22 Awesome Outfits for Holiday Gatherings for Men, Women, & Children this Winter

Outfits for holiday get-togethers can be dressy to casual, warm to cool; celebrating Christmas around the world means everything from a cabin in the snow to a condo on the beach. This holiday season check out all of the awesome outfits for holiday gatherings that parents and children alike will love. Keep yourself looking calm and collected while the kids look cute and cool in all of these seasonal outfits for holiday celebrations and beyond!

Dudley Stephens

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

When we think of perfection and innovation, we think of the team working at Dudley Stephens. Every piece they have is crafted from recycled fabrics. They are also versatile and durable, ensuring that you will get the most comfort and wear from every piece. Our favorite reason to shop from Dudley Stephens is that it was founded and is run by a team of fabulous women.

One of the most popular selections from Dudley Stephens is the Cobble Hill Turtleneck. This tunic-style turtleneck is soft and curve-friendly. Offered in either Vello Fleece for chilly days, or Terry fleece for milder weather, the Cobble Hill Turtleneck is available in over 10 different colors. Its collar can be fashioned either standing straight up or folded down.

If we haven’t said it enough, let us say it again. We love the Cobble Hill Turtleneck so much, we grabbed a second one in red. All of the Cobble Hill Turtlenecks will pair well with slim black pants for an evening out or yoga pants for a day spent lounging on the sofa next to a crackling fireplace. The red Cobble Hill Turtleneck is our go-to piece for upcoming holiday parties and of course, let’s not forget Valentine’s Day.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

What can we say? We love turtlenecks especially when they’re designed by Dudley Stephens! The Greenpoint Turtleneck offered in Heather Grey is the perfect sweater to wear with blue jeans or sweat pants. For days when you have to leave the house, rest assured, you can still take comfort and style with you when you slip on this sweater. This midi-length turtleneck has long sleeves and is made from 100% polyester. Its signature stand-up collar will keep unpleasant breezes at bay.

For grey, winter days, give yourself a pop of color when you wear the Bleecker Pullover. Available in several color combinations, our favorite is the neon pink pullover with yellow and cobalt. Made with Polartec® fleece, this thermal pullover will keep the nastiest chill in the air away while you navigate your day. Its oversized fit makes it incredibly comfortable to wear.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Bleak winter days never looked or felt so good thanks to this amazing collection by Dudley Stephens. Embrace warmth, comfort, and fashion when you dress up in one of these incredible sweaters. For frigid days when you have to leave the house, make sure you stock your closet with Dudley Stephens.

Cobble Hill Turtleneck | Greenpoint Turtleneck in Heather Grey | Bleecker Pullover in Neon Pink/Yellow/Cobalt
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22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

The holiday season is filled with magic, but it’s not as fun if you’re not dressed in clothing that will keep the chill at bay. Appaman takes the magic experienced by children in nature and transforms it into clothing styles that provide functionality and fun.

Experiencing the holiday season requires specific clothing types for different occasions. When it comes to outerwear, it must be comfortable and warm while looking great. The Woodland jacket seen here in Buffalo Plaid is everything you could want in a jacket. Warm and soft, this jacket helps will zip right up and help him look the part when he’s out exploring this season. This jacket is lightweight enough to let keep him moving without uncomfortable bunching and pulling. Similarly, the Bomber Jacket, Rosin is another awesome choice if you want a trendier look with a double zipper, two layer jacket.

For a more vintage look, the Heritage Cord Jacket Sierra fits the bill. Soft and durable, he will love this sherpa lining that goes all the way to the collar. The buttons give this jacket a rustic look and feel while the corduroy outer can accompany him outside on an adventure or even to Christmas dinner. Feeling like you need more from your outerwear?

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

For a lighter option, she may enjoy the Nikki Bomber Jacket in Black Luxe. This gorgeous jacket is soft enough to keep her cozy but light enough that she can wear it as a transitional piece between seasons. With a soft collar and an easy zipper, she can pair this with any of her favorite holiday outfits to keep her toasty and ready to play.

The key to cooler weather is layering, so finding shirts that can be adorably worn on their own or make the perfect foundation for those long winter days can be tricky. Choose a tee that is soft with a little bit of stretch, like the Bulldog Tee. These 100% cotton shirts can make a great base layer to any winter outfit, but they also stand out on their own with their soft quality and adorable design. Add the Half Zip Hoodie and the Gym Sweats for a day of play.

Is it even a winter wardrobe without some plaid? Keep the flannel look but add a dash of warmth with the Snow Fleece in Windom Plaid. This plaid is great for layering over a tee or under his favorite coat for those extra-snowy days. This warm color scheme looks great with the Skinny Twill pants in Pecan or Moss.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter
22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Start her layers with the Willow Top in Blue Depths over her favorite leggings or jeans. This top is like wearing a warm cloud. Fully lined so she’ll stay cozy, this adorable top is lightweight enough to wear on a more mild day. Top off her look with the Apex Puffer Vest, Metallic Rainbow when she’s ready to start her next adventure. This fully insulated vest has deep, puffy pockets so she will have everything she needs to play while she’s staying warm.

While finding beautiful, functional clothing is typically a task that is hard to undertake, Appaman makes dressing kids easy this holiday season. Keep the youngest members of the family warm and stylish with Appaman.

Bomber Jacket, Rosin | Woodland Buffalo Plaid | Heritage Cord Jacket Sierra | Puffy Coat, Black | Skinny Twill Pecan | Skinny Twill Moss | Bulldog Tee | Snow Fleece Windom Plaid | Half Zip Hoodie | Gym Sweats, Orange | Willow Top Blue Depths | Apex Puffer Vest Metallic Rainbow | Nikki Bomber Jacket Black Luxe
Appaman | Facebook | Instagram | Youtube | Pinterest


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

The days of shopping ’til you drop for that perfect seasonal outfit are on their way out the door because FabKids takes the work out of coordinating little outfits while simultaneously delivering quality outfits to your door. This holiday season, dress your children with FabKids and they’re certain to be the cutest kids around the table.

Keep the chill at bay with the adorable warm selections offered by FabKids. Brightly colored and ready for a turkey dinner, the Plaid Flannel Long Sleeve Shirt is as warm as it is soft. With darling white buttons down the front and adorning each pocket, he can wear this tucked and tidy or over a t-shirt while playing a game of football outside with his cousins.

For a merrier look, the Plaid Hooded Overshirt is a look that Kris Kringle himself would envy. This shirt is intended to be layered, so it’s lightweight and softer than your average flannel. Black buttons give this overshirt a sleek look so it’s perfect to pair with dress slacks or his favorite jeans.

If he needs a new pair of jeans (that are certain to become his new favorites), then the Skinny Jean are a must. This soft denim stretches and moves with him, so uncomfortable bunching is a thing of Christmas-past. Featuring an adjustable waist, snap closure, and a working zipper, these jeans can be worn to the playground or to Church and will last for more than just one season.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Keep the plaid rocking through the family with the On Beat Outfit. This soft, lightweight dress is made for layering. No matter what climate she’s in, she’ll rock this look. A single-button closure at the nape of the neck means that this dress is a no-drama, comfortable option for all your holiday adventures. It falls just below the knee, so she’ll be wearing it from Thanksgiving to Valentine’s Day, even if she grows a few inches. Pair it with leggings and boots for a sleigh ride or tights and pumps for a more dressed-up look.

We aren’t sure who is going to love this outfit more: her, or Mom! This Pretty In Plaid Outfit is a total throwback to all the best parts of fashion in the 90s. This jumper is 100% cotton and perfectly pairs with the Long Sleeve Mock Neck Tee. Dainty pockets adorn the front while oversized buttons bring this entire ensemble together. These straps are adjusted easily with hidden buttons, so even if she grows faster than we expect (when don’t they, right?) she’ll be able to wear this outfit as long as she likes.

Every gal needs some basic layering gear, and the Soft Legging paired with the Long Sleeve Mock Neck Tee can be worn on their own, but just in case they leave plenty of room for vests, jackets, boots, and sweaters. The soft elastic waistband does not squeeze into the skin leaving uncomfortable marks, but they are oh-so-soft and the best option for those days where she’ll go from reading by the fire to throwing snowballs at her brother in the same breath.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Speaking of snowballs, don’t forget to keep their feet warm and dry this season! She will love the Unicorn Printed Lace Up Boot and it’s sturdy construction. The upper is wipe-clean polyester and the bottom will keep the water and snow out of her shoes all day long. The bright purple won’t be hard to keep an eye on, even in the most wintery weather, and she’ll love the sweet unicorn pattern. For him, the Sherpa Lined Lace Up Boot is the obvious wintery winner. These duck boots are weatherproof and perfect for puddle-jumping and snowman building. The lining inside is unbelievably soft and warm, no matter where his day takes him, we’re certain he will want to wear these all day long.

For daily wear, the Light Up High Top Dino Sneaker will have your dinosaur-lover stomping all over. These sneakers have a three-strap closure so his foot will be secure, and the bottom of his shoe will provide a colorful light show with every step. The frill on the back will leave his friends guessing-what type of dinosaur will he be today?

For her, the Tall Moto Boot is the classic winter boot that can be paired with every single one of her favorite outfits. The combinations are endless! Is she a city girl or does her heart belong in the countryside? No matter, these comfortable cowboy boots feature original stitching and a low heel for easy, all-day wear. Regardless of her agenda, she’ll be able to pull these on and go!

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter
Read More: How to Light a Menorah

Your little ones may still be writing their secret letters out to Santa and whispering their holiday plans to each other, but parents, check off finding the perfect holiday outfits off of your list. FabKids has already thought of everything and it’s more than we could have ever wanted.

Plaid Flannel Long Sleeve Shirt | Skinny Jean | Plaid Hooded Overshirt | Sherpa Lined Lace Up Boot | Light Up High Top Dino Sneaker | Soft Legging | Pretty In Plaid Outfit | On Beat Outfit | Long Sleeve Mock Neck Tee | Unicorn Printed Lace Up Boot | Quilted Tall Moto Boot
FabKids | Facebook | Instagram | Youtube | Pinterest


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Don’t take it off. There’s literally no reason to take off loungewear that feels incredibly amazing and keeps you relaxed, sane, and horribly comfortable. Designed by OCIO, they created the reason to stay so comfortable in your clothes, sized XXS – 4X, so you probably won’t feel like ever taking them off, because, why not? This holiday, grab the Classic SoftCore Hoodie in Bloom that makes you feel at home no matter where you are, lazy boy, laundry room, or living it up at the bookstore with a java.

SIne it’s comfortably fitted to your form and rests at your hips, leggings, jeans, skirts, or shorts, it’s a versatile statement piece that screams…I love this! And who wouldn’t with a flattering fit, soft rib cuffs, a front pocket, and of course, the double-lined hood to block out anything unnecessary.

Might as well complete the ensemble with the mid-weight choice of the Classic SoftCore Jogger in Bloom to hug all the right feminine curves with pockets that don’t scrunch, or the Classic SoftCore Short in Bloom to allow those legs to breathe and be revealed. Either one you choose for yourself or a sister you hold dear, the custom fabric blend will have you swimming in supportive, flexible, and silky soft luxury.

If you are wondering, what’s to hold in your lovely bosom underneath all of that comfort, the Double Scoop Tank in Bloom combines a balance of support, stretch, and the same softness against your bust. In a nutshell, it’s the loungewear piece that allows your natural form to hold up nicely while comfortably keeping everything in place without discomfort.

Read More: 4 Things You Didn’t Know About the History of Silent Night

With everything in the world stressing you out and creating uncomfortable situations, this holiday, relaxation comes in the form of organic, biodegradable materials, and a lovely Bluesign® Certified Dyehouse color that makes your clothing… simple. Now that’s a gift worth indulging in!

Classic SoftCore Hoodie in Bloom | Classic SoftCore Jogger in Bloom | Classic SoftCore Short in Bloom | Double Scoop Tank in Bloom
OCIO | Facebook | Instagram

Mott & Bow

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

City sidewalks (busy sidewalks) aren’t the only ones who need to be dressed in holiday style this year, and they have nothing on the hustle and bustle that families experience during the holiday season. Instead of choosing between boxers or briefs for Dad this holiday season, give him the gift of beautiful wardrobe staples that will keep him looking and feeling his best all year long with Mott & Bow.

For a denim that can go from date night to dinner at the in-law’s house, the Straight Mosco featured here in medium blue, is the perfect choice. A lightweight denim with a forgiving stretch, these jeans will move with his movements and avoid the uncomfortable bunching that can sometimes accompany jeans. Pair these jeans with a polo for an evening on the town or a button-down for a more dressy look.

The Slim Button Down Collar – Kent is a soft blue that complements any skin tone. A classic Oxford-style shirt, this button-down can be worn tucked or untucked and offers a button-down collar or a spread collar. He can choose his style while looking and feeling his best.

When it’s time to get cozy, he’ll adore the Classic Cashmere Crew – Bergen. This sweater will look and feel amazing over a t-shirt for those mild winter days, or over a button-down for that snowy New Year’s night. However he decides to wear it, he’ll be able to enjoy this soft sweater year-round. Paired with his favorite denim, or the Straight – Mercer (seen here in Light Khaki), he will be ready for anything this holiday season tosses his way and he’ll be doing it in style.

This holiday season, give him the gift of year-round comfort and style with Mott & Bow.

Slim Button Down Collar – Kent | Classic Cashmere Crew – Bergen | Straight – Mercer – Light Khaki | Straight – Mosco – Medium Blue
Mott & Bow | Facebook | Instagram | Twitter


There are some people in our lives whose beauty seems so effortless. This holiday season, give a gift that captures her essence with Splendid and their line of versatile clothing.

This holiday season, the Cella Jane Sweater Coat captures our attention. This soft piece combines the coziness of a sweater knit with the look of a tailored coat. Throw this oversized piece over a pair of jeans and a tank for a Hampton-esque look for the family gathering. Or, combine it with your favorite pair of slacks and a blouse when you return to the office after the holidays. The front pockets and long sleeves make this as functional as it is beautiful. However she decides to wear it, this Cashblend fabric (a perfect blend of cashmere and wool) will leave her feeling and looking warm and ready to conquer her day.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

There’s nothing better than the perfect oversized sweater unless that sweater is the Cella Jane Relaxed Sweater. This comfortable sweater has a classic look and an irresistible feel. This sweater is crafted with a wool blend so it’s going to keep her warm, but the rib trims give it that certain je ne sais quoi that everyone can agree makes this the perfect piece for fall, winter, and early spring. Wear it tucked in or untucked, either way, she’ll find herself reaching for it again and again.

Cella Jane Sweater Coat | Cella Jane Relaxed Sweater
Splendid | Facebook | Instagram | Twitter | Pinterest

Carve Designs

Founded in 2003 by two friends: Jennifer and Thayer, Carve Designs was initially a surf apparel shop specializing in boardshorts made for real women with real bodies. Since then, Carve Designs has grown, offering both beach and lifestyle apparel for women. Real women with real bodies. We’re super-excited to share our favorite Carve Designs with you!

Comfortable like your favorite pair of sweats but definitely more stylish, the Carson Jean is a stretch denim that’s relaxed in both the hips and the thighs. Made with 99% organic cotton and 1% spandex, the Carson Jean is perfect for both busy days and casual getaways. Sizes run large so be sure to purchase one size down from your regular size.

The cooler days ahead require a little extra comfort. If you’re looking for something to pair with your Carson Jean or Carson Cord, Carve Designs has the perfect solution. Grab one of their Rockvale sweaters. The Coral Bold Stripe sweater will pair perfectly with the Carson Cord. We love wearing the Birch Bold sweater with our white Carson Jean. All of the Rockvale Sweaters have a kangaroo pouch, a drawcord neck, and provide a relaxed fit making them the perfect sweater for slow days next to a crackling fire.

Carve Designs has plenty of options to keep you warm and comfortable when you’re on the go. Whether you’re running errands or grabbing coffee with a friend, don’t walk out the door without the Laughlin Vest. Made with recycled polyester, this fully-lined fleece vest is perfect for layering! The side pockets have an invisible snap enclosure that will keep your keys and wallet secure.

Providing UPF 50 protection from unpleasant UV rays, the Carson Cord offers all the style of a classic boyfriend jean with a corduroy touch.  These relaxed fit pants are made with a soft stretch corduroy and can be styled either cuffed or uncuffed. Available in multiple colors, our favorite is the Saddle. If you need help finding the right size, visit Carve Designs and check out their fit predictor for the perfect fit every time.

Loungewear never looked better thanks to the Leland Top! Pair it with the Carson Jean or your favorite sweats. However you wear it, one thing is for sure. You’ll love its loose fit and classic V-neck cut. Perfect for laundry days or movie night, the Leland Top will always help you feel right at home.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Speaking of crackling fires, Carve Designs has additional options for chilly, winter days. We love their Fireside Sweater. Made with soft, plush yarn, this open-front sweater features deep pockets and is a relaxed fit. The Fireside Sweater is available in two colors. Our favorite is Saddle. Wrap yourself inside this sweater and curl up next to a warm fire with a glass of wine and your favorite person!

If you’re looking for comfort and fashion, look no further than Carve Designs. Let Carve Designs dress you for colder weather. Always fashionable. Always fun. Fill your closet with clothing from Carve Designs.

Carson Jean | Carson Cord Saddle | Rockvale Sweater Birch Bold | Fireside Sweater | Laughlin Vest Heather GreyLeland Top
Carve Designs | Facebook | Instagram | Twitter | Pinterest | TikTok


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Sometimes the search for the perfect black blazer seems daunting! But never fear, with DuetteNYC, the perfect black blazer is here just in time for the holiday season. Sexy, sophisticated, and sustainable, all of the monochrome clothing from DuetteNYC is made to mix and match, travel along with you, and look fabulous for every occasion. DuetteNYC offers sustainably made fashion choices that keep you looking chic in the city or comfy at home no matter where your holiday takes you!

Whether you are headed out on the town to simply to the office the Lux Long Blazer is perfect for pairing over jeans and a tee or even a dress. This single button elongated blazer features a slim stretch design with a fit that flatters. Designed using DuetteNYC’s sustainable, exclusive premium knit fabric this soft blazer is easy to wear for just about anything!

Pair the blazer with the Lux Boatneck Tunic and the Lux Perfect Flare Leg Pants for a seasonal look that will never go out of style. The Lux Boatneck Tunic features a 3/4 length sleeve, side slit detail, and tunic-length silhouette. Designed in DuetteNYC’s sustainably forested fabric, this tunic is sleek and classic. When paired with the Lux Perfect Flare Leg Pants with their elastic waist, wider waistband, and easy pull-on style featuring 40-way stretch, she will be ready and out the door in no time this season!

Lux Long Blazer | Lux Boatneck Tunic | Lux Perfect Flare Leg Pants
DuetteNYC | Facebook | Instagram

Buckle Me Baby Coats

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Winter is finally here, and the holidays are fast approaching! While you’re shopping for your little one, be sure to grab them something that they can use to enjoy the cold season. While jackets and blankets are cute, it can be unsafe for your kids to wear them while driving around to see the holiday lights. Buckle Me Baby Coats brings us a line of coats that are not bulky and so safe for your little ones to wear every car ride!

Buckle Me Baby Coats are crash tested, CPST and CPSC approved, making them the safest coats for car rides! These warm and super stylish coats, like the A-Doe-rable will keep your kids warm while they run around the playground in the snow or as you’re waiting for your spouse to help you with a flat tire. These coats simply fold over the harness and secure tightly, without bunching in the back.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

With styles like the Little Darling and the limited addition A-Doe-rable, there is a coat for every kid in the family! Buckle Me Baby Coats are made to keep your family safe and warm all season long and make for cute and practical gifts!

A-Doe-rable | Little Darling
Buckle Me Baby Coats | Facebook | Instagram | Twitter | Pinterest


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Living an active lifestyle doesn’t mean you’re constantly wearing basketball shorts and cotton t-shirts, in fact, Rhone has carefully curated a line of men’s clothing that is designed to move with him regardless of whether he’s on the basketball court or in court. Designed to provide stretch and breathability, Rhone clothing can accompany him anywhere his busy life takes him.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

With moisture-wicking Polartec® Delta™ Lightweight mesh fabric with cooling yarn technology and flatlock stitching for chafe-free seams, he’ll be crazy cozy in his Delta Pique Polo. This comfortable fit is meant to make him comfortable in every way.

Flex-Knit™ fabric is a unique best-seller and it’s no surprise. Pants that have some “give” and stretch while looking as great as they feel are a no-brainer, and that’s why he needs the Commuter Pant under the tree this season. Wear it to the office and go straight to the park for a quick game-no matter what, this pant fits the bill. A gusset provides a comfortable fit and a media pocket ensures that his gear will stay close to him.

For a more tailored look with that same lightweight feel, the Commuter Jogger is what he needs. With all the features we love about the Commuter Pant, this jogger features a look that will turn heads all while feeling like his favorite pajama bottoms.

This season, give him the gift of fashion that feels good with Rhone.

Commuter Pant | Commuter Jogger | Delta Pique Polo
Rhone | Facebook | Instagram | Twitter | Youtube | Pinterest

Neon Buddha

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Snuggle up this season with gorgeous boho sweaters from Neon Buddha. Let’s start with the Tied & True Pullover. This cozy top features a textured knit-like material, long sleeves, flattering length and cute tie-closure with wooden accents.

Sport this slip-on gem with your favorite skinny jeans and boots for a winter look, or throw on with shorts and your favorite sneakers for four seasons of style. The options are endless!

You deserve a break from all of the holiday craziness, so why not kick back and relax in the Ever After Pullover? This cute and chunky sweater brings the drama of a wide-ribbed cowl neck and adds some fun vertical fringe trim.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

This long sleeve solid top features an intricate criss-cross pattern and will keep you stylishly warm all winter long. The Ever After Pullover is made for your perfect fit. It has a curve-hugging shape which gives the look of a chunky sweater without the typical bulkiness. We adore it and think you will, too!

On a chilly day, there’s nothing more comforting than snuggling up in a cozy sweater, right? The Begonia Pull-over is lightweight but warm, and will give you an extremely soft and comfortable fit. We especially love the lace-up arm detailing, which reminds us of festive holiday ribbons and bows. Make her holiday wishes come true by placing some Neon Buddha under the tree this year!

Tied & True Pullover | Ever After Pullover | Begonia Pull-over
Neon Buddha | Facebook | Instagram | Youtube

The Children’s Place

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Specializing in children’s apparel for 40 years, no one does better at creating lasting fashion for children than the designers at The Children’s Place. With a huge selection to choose from, parents will love dressing their kids from head to toe! Never run out of options for your growing children when you shop from The Children’s Place.

You’ll love the look and he’ll enjoy having all kinds of fun while wearing the pants in this 2-pack of Boys Straight Jeans. This set comes in two colors: Dark Jupiter and Carbon wash. Each pair is 100% cotton and comes with 5-pockets. We love the inner adjustable waist tabs that allow parents to customize the fit.

The Boys Stretch Straight Jeans will give your growing boys all the comfort they need! They come pre-washed which will reduce future shrinking. We love how soft these jeans feel!

For fancier occasions, style your favorite fellow with the Boys Uniform Stretch Pull-On Chino Pants. Available in multiple colors, we love the black pants for school picture days. The Boys Uniform Stretch Pull-On Chino Pants are made with cotton and spandex.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

For older boys, check out the Boys Uniform Stretch Chino Pants. While these are not pull-on pants, this two-pack is still stylish and perfect for more formal occasions. The pants in this two-pack are available in three different color combinations: black, flax, and white. They are also available in three different styles: slim, regular, and husky.

For chilly days, dress your sons up in the Boys Thermal Henley. This pull-on shirt is machine washable and has long sleeves. Parents will love that this shirt can be styled with any of The Children’s Place denim jeans as well as their chino pants.

The  Boys Uniform Basic Layering Tee works well as either a standalone shirt or underneath a sweatshirt. Available in multiple colors, the Boys Uniform Basic Layering Tee can be purchased individually or in packs of 2s, 3s, 4s, and 5s. Shirts purchased in the multipack come with varying color combinations. Parents will love the versatility of this shirt. Kids will love that this shirt is tagless and won’t make their necks itch.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

For bitter cold days, send your kids to school wearing the Boys Uniform Zip Up Mock Neck Sweater. This zip-up sweater has a rib-knit mock neck that will keep cold air +away. It’s also pre-washed, making it super soft.

Family fun was never more adorable thanks to the fabulous collection of cotton pajamas offered by The Children’s Place. First on our list of cuteness, are the Family Christmoose Snug Fit Cotton Pajamas. This two-piece collection comes with a long-sleeved shirt and plaid, pull-on pajama bottoms.

If wearing a merry moose to bed isn’t your child’s cup of tea, check out the Family Winter Bear Snug Fit Cotton Pajamas. Both pieces in this collection have the same bear and tree print all over. These pajamas are so soft, your child will sleep comfortably all night long.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Last on our list of favorite pajamas is the Unisex Kids Family Believe Snug Fit Cotton Pajamas. These pajamas are the perfect pair to wear for a Christmas Eve viewing of The Polar Express. The top has long, red sleeves. The body of the shirt is white with ‘Believe 2021’ written across it. The plaid pajama bottoms are super cute and comfortable with an elastic waistband.

The Children’s Place has an endless selection of clothes for every occasion. Whether you need school clothes for picture day or play clothes for summertime adventures, you’ll never have any problem finding what you need for your kids. Shop at The Children’s Place and watch your kids grow in style.

Boys Straight Jeans – 2 Pack Basic | Boys Stretch Straight Jeans | Boys Uniform Stretch Pull-On Chino Pants | Boys Uniform Stretch Chino Pants – 2 Pack | Boys Thermal Henley | Boys Uniform Basic Layering Tee | Boys Uniform Zip Up Mock Neck Sweater | Unisex Kids Family Christmoose Snug Fit Cotton Pajamas | Unisex Kids Family Winter Bear Snug Fit Cotton Pajamas | Unisex Kids Family Believe Snug Fit Cotton Pajamas
The Children’s Place | Facebook | Instagram | Twitter | YouTube | Pinterest | TikTok


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

In the cool of winter short-sleeved shirts just won’t do the trick, and the typical long-sleeved versions aren’t formal enough for holiday events. The 2.0 Collar-free Long Sleeve Shirt has been redesigned for a far more comfortable, softer fit in the fabric composition while looking fabulously chic. Engineered with NASA technology for unprecedented temperature regulation, these long sleeve shirts are not your typical everyday shirt. Stain-resistant and machine washable, the 2.0 Collar-free Long Sleeve Shirt has revolutionized what it means to wear high-quality clothing.

Even after a long, busy day, your new long sleeve shirt will be free of wrinkles and stains, ready to step into the nightlife and any holiday party you have planned! Cheegs fits your man’s needs, no collar or comfort limitations required.

2.0 Collar-free Long Sleeve Shirt
Cheegs | Facebook | Instagram


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Get her everything she loves about Mer-Sea this holiday season wrapped up into one gorgeous kimono. Featuring a super-soft cashmere knit, the Chelsea Kimono can take her from the airport to Christmas dinner without stopping to change her outfit.

The gorgeous Chelsea Kimono is elegant and soft with a shape that flatters all body types. Chelsea drapes elegantly over her back and the sleeves snugly fit her wrists, adding that extra sense of sophistication that make this piece so special. Available to own in a selection of peaceful earth tones, the Chelsea Kimono is ready to make her holiday season oh-so-cozy and memorable for all the right reasons.

Chelsea Kimono
Mer-Sea | Facebook | Instagram | Twitter | Pinterest


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Make your Christmas extra-special this year with Tees2UrDoor. Add a fun and colorful touch to your holiday attire with this vibrant Make it Merry Christmas T-shirt. Made from 100% preshrunk cotton, the unisex tee features a printed “Make it Merry” design in various “Christmas-y” patterns, including candy canes, decorated trees, snowflakes, and lights. 

Looking for a lightweight cardigan to take the edge off of crisp winter nights? Pair your tee with the Lucy Lightweight Slub Cardigan for some candy cane-striped holiday style! This 100% polyester, stretchy, and machine washable cardigan is available in four sizes. The versatile, open-weave cover-up comes in 23 (yes, that’s 23!) vibrant and classy colors. Wow! Even better than that, its price is extremely affordable, so you can grab several and switch up your style all season long!

For that tough-to-buy-for tween, snag a Peace Love Christmas T-Shirt, too. Made with a cotton and polyester blend, it’s super comfortable to wear all day. This fun printed shirt features Santa Claus making a peace sign with his signature glove, a sassy leopard heart, and a fully decked-out Christmas tree. Prepare to peace out this season!

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

To top it off, add a Varsity Cardigan to the cart. Snuggle up like a polar bear in this cozy 100% polyester outerwear. The lightweight open-front sweater has four buttons to close it up when a chill hits the air. Warm your hands or carry phones and candy canes in the soft front pockets. While we love red for Christmas, it comes in many other colors, so you can enjoy Tees2UrDoor with just about any outfit this season and then some!

Varsity Cardigan | Peace Love Christmas T-Shirt | Make it Merry Christmas T-Shirt | Lucy Lightweight Slub Cardigan
Tees2UrDoor | Facebook Instagram Twitter Youtube


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

If soft, stretchy denim is your jam, then Mavi has the selection you need this holiday season. Whether you are gifting your guy, or yourself, or shopping for other’s on your holiday list, Mavi’s denim is a cozy, comfy choice this season.

For him we love the Mavi Men’s Matt Relaxed Fit Straight Leg Jeans. Featuring a comfy mid rise fit with a roomy yet tailored leg, these jeans offer maximum stretch while still maintaining their shape. Soft and supple, these jeans are worn in and ready for wear right out of the box!

Pair with the Mavi Men’s Rio Shirt in all seasons. Stylish and on-trend, this button up shirt features a vintage wash and is both lightweight, yet warm enough to wear all year.

Finally, for her, the Mavi Women’s Kathleen is a timeless classic. The ankle-length boyfriend fit is cozy, comfy, and provides the perfect amount of stretch. Made of organic cotton with just a bit of slouch and distressing, these jeans are versatile for every occasion wear.

This holiday season Mavi has all the denim you need to keep everyone comfy, cozy, and oh so stylish!

Mavi Men’s Matt Relaxed Fit Straight Leg Jeans | Mavi Men’s Rio Shirt | Mavi Women’s Kathleen
Mavi | Facebook | Instagram | Twitter | Pinterest

Motherhood Maternity

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

The weather is changing and with it comes more and more layers! If you’re breastfeeding you may wonder how on Earth you’re going to feed your little one with a sweater or jacket on. Don’t worry about it, because Motherhood Maternity has you covered! With their magnetic x me motherhood collection, you’ll be able to nurse your little one easily and comfortably.

The Magnetic Me x Motherhood Maternity Nursing Hoodie is perfect for a comfortable fall day. With its casual design, it can go over nearly any outfit you wear! Nursing is a breeze with its hidden magnetic fasteners. Simply “pop-off” the magnets and your baby has easy access to nurse! The Magnetic Me x Motherhood Maternity Nursing Hoodie has magnetic access on both sides, so you don’t have to worry about tugging and pulling your jacket to breastfeed.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Wanting something lightweight but will still cover you while you nurse? Sick of nursing covers going over yet another layer? The Magnetic Me x Motherhood Nursing Cover Nursing Cardigan has everything you need to stay covered without adding on too much weight. This long sleeve and drape neck design are perfect for wearing to the office or on a walk around the neighborhood. You can wear it as a traditional cardigan, or use the magnetic design to feature a drape neck. When you need to nurse your little one, you can simply use one side of the magnet snap for a little more privacy.

Breastfeeding this fall has never been easier than with Motherhood Maternity! Magnetic nursing wear is something you definitely need to keep you and your little one comfortable this fall.

Magnetic Me x Motherhood Maternity Nursing Hoodie | Magnetic Me x Motherhood Nursing Cover Nursing Cardigan
Motherhood Maternity | Facebook | Instagram | Pinterest

Paper Cape

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

While visions of sugar plums dance in their heads, make sure they look the part in their new favorite clothing from Paper Cape. These pieces are delicately crafted to not only be beautiful, but comfortable and durable, too. Whether you’re asleep or awake, keep the magic of the holiday season alive with Paper Cape.

Snuggle up as you wait for Santa with the terrifically twirly Midi Lounge Dress in the Candy Cane pattern. This lounge dress is perfect for baking cookies, watching your favorite holiday movie, and trying to sneak a peek at St. Nicholas as you drift off to sleep. This 100% Pima Cotton is extra soft, so she will want to wear it all season long.

The little gentleman of the home will look the part in his Classic Pajamas featured here in Red. These pajamas are constructed with Peruvian Pima cotton, known for being the world’s softest, strongest cotton. The sweet accents of piping and lapels make these pajamas both comfortable and classic.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Say “cheese”! These sweaters will be the must-have top for the family photo this season. For her, the Madeleine Sweatshirt is the perfect staple she’ll be able to wear all year long. The wide sleeves add a touch of elegance while the wide collar will make her feel oh-so-dainty. Perfectly paired with a skirt and boots or leggings over a dress, this sweater can take her anywhere she needs to be this season.

For him, the Maxwell Pullover with Bear Pocket is an undeniable winner. These sweaters are both so soft, but his little pocket with the bear accent is almost too adorable to “bear”. Whether he’s wearing it for a holiday program or running around the yard playing football with his cousins, he’ll look as good as he feels.

Paper Cape is intended to be a hand-me-down, and these pieces are built so carefully and designed to last, so no matter where their holidays take them down the road, their hearts are sure to warm up knowing that someone they love is dressed in Paper Cape.

Midi Lounge Dress-Candy Cane | Classic Pajamas-Red | Madeleine Sweatshirt | Maxwell Pullover with Bear Pocket
Paper Cape | Facebook | Instagram | Pinterest

Rose Paulino

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Fashionistas know that a denim jacket is a staple in every woman’s wardrobe. But to take your jean jacket game up a notch, you will be in awe over the Harper. Labeled as a dramatic fringe western denim jacket, the Harper uses a traditional jean jacket to showcase a long, black fringe along the back and arms. This jacket is a head-turner and will become your go-to for cool nights out on the town. Even the most casual outfits can be leveled up by simply wearing this jacket. Rose Paulino uses their bold voice to create stylish women’s apparel for all body types and sizes.

Harper- Dramatic Fringe Western Denim Jacket
Rose Paulino | Facebook | Instagram | Twitter


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Dress up in style this holiday season with celebrity-loved kid’s fashion from Kultkid. They design stylish gender-free kid’s clothing inspired by urban street style. The lavender

Oversized Kult Logo Tshirt with Resistain® is made from ultra-soft premium cotton, has drop shoulders, oversized sleeves, and is designed to resist stains (including juices & smoothies, soups & sauces, milkshakes & ice cream, and water & rain).  

Liquids will drip straight from the t-shirt for heavier stains; just wipe and go. So this holiday season, impress family and friends with your keen sense for fashion with kid’s stylish clothing from Kultkid.

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Oversized Kult Logo Tshirt with Resistain® in Lavender
Kultkid| Facebook | Instagram | Twitter | Pinterest

OshKosh B’Gosh

22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

OshKosh is a family favorite everywhere and has been for years. Winter, spring, summer, or fall, OshKosh has the styles parents love their kids to wear and kids love to wear for play. From dressing up to tucking them in for the night, and everything in between, OshKosh has cute and classic looks for kids.

This winter a few of our favorites from OshKosh include soft and cozy winter styles our littles love to wear outdoors. Whether they are headed to preschool or the park, these easy to wear, mix and match styles of long sleeve tees, sweatpants and cozy half-zips and hoodies keep them warm while at play, without complaint. Even if you have a child who hates tags or despises wearing a coat, these fluffy, comfy looks will keep them warm all winter:

Half Zip Sherpa Pullover Camel | Zip Up Fuzzy Lined Jacket | TreeRex Graphic Tee Shirt | 3 Pack Long Sleeve Tees | Sun Washed Pocket Henley | French Terry Joggers in Forest | Button-Front Plaid Flannel Shirt
OshKosh B’gosh | Facebook | Instagram | Twitter


22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter

Clothing for her can be simply and trendy this season with so many affordable styles from WMNSWR. From the Christmas tree farm to the kids’ holiday program at school, WMNSWR has the outfits you need to look and feel your best.

This season our favorites include a few staple pieces:

  • Kayla Grey Steele Long Sleeve Tee: Alone or as a layering piece, this sold long sleeve pocket tee is easy to wear with jeans or leggings.
  • Darby Optic Plaid Shacket: A flannel and a jacket, this plaid shacket can we worn with jeans or a dress and its black and white pattern is a classic.
  • Shea Brick Burgundy Babydoll Dress: Babydoll dresses never go out of style, with a pair of boots and tights, this waffle knit dress will keep you cute and on-trend all season.

Kayla Grey Steele Long Sleeve Tee | Darby Optic Plaid Shacket | Shea Brick Burgundy Babydoll Dress
WMNSWR | Facebook | Instagram | Pinterest

Shopping is oh so simple this season with all of these awesome outfits for holiday wear and the ability to find them all online! Kick back in front of the fire, grab a hot toddy, and enjoy shopping for all the holiday clothing you, the hubs, and the kiddos need this season of celebration! Happy Holidays!

Check out this article on 14 Fancy Holiday Outfits & Accessories for the Family.



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22 Awesome Outfits For Holiday Gatherings For Men, Women, & Children This Winter



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Kristin dePaula
Kristin dePaula
Kristin is a Montessori Mama who spends her days working as a lawyer with at-risk youth and her nights chasing her 4 boys on their latest adventure. She spends a significant amount of time in the kitchen creating healthy, organic, and delicious meals for her family, reading books with her boys, and at the soccer fields. Aspiring to make a difference in lives of others one child at a time, Kristin is passionate about social justice, early literacy, and early childhood education. While she loves scarves and boots, Kristin lives at the world's most famous beach with her husband, kids, extended family, and enough pets to open a zoo.

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