15 Easy Winter Outfits That Will Make You Love The Cold

December 5, 2024 Ashley Rollins

Cozy winter fashion could be your saving grace this season.

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Are you already dreading the colder weather? Well, cozy winter fashion will be your saving grace. Depending on your location, you may already have your wool coats and cable knit sweaters pulled out of the closet. If not, in a matter of days you’ll want to.

If you’re not used to the cold weather, remember that layering will be your fashion sidekick during the winter. For the chicest and warmest winter outfits, we suggest layering with leggings, tights, cozy winter hats, scarves, and the thickest socks.

With our holiday schedules getting busier—including those gatherings with friends and family and holiday office events—we don’t want to just look like a walking pile of heavy clothes. Instead, we’re sharing winter outfit inspiration for any chilly day coming your way.

Comfy, Casual Winter Outfits

There are easy ways to create cute, everyday winter outfits without feeling like you’re just piling on everything in your closet. Wearing sweaters, long sleeves, coats, and warm socks will be a great place to start, since you probably already have these items in your closet. Plus, the winter season gives you a chance to mix and match this pieces to create casual outfits for any winter day.

Layers on Layers

Shop: Coat | Cardigan | Trousers | Handbag | Boots

The blustery weather during the winter months makes staying warm difficult, so layering fabrics and lengths of clothing is the key to staying cozy. Pair a loose-fitting sweater or cardigan with trousers or casual pants for a comfortable base layer. You can play with colorful pairings or go for a monochrome look, but top this layer with a long coat to keep the warmth in (bonus points for a pattern here, too). Finish the outfit with a leather bag that you can toss over your shoulder and boots.

Dress & Sneakers

Shop: Blazer | Dress | Bag | Sneakers | Bracelet

Sweater dresses can make easy, casual winter outfits. We love a ribbed sweater dress for the added texture, especially when worn with retro sneakers. You can keep this outfit casual. yet elevated, with accessories like gold hoops, a layered necklace set, or nothing at all, if that is your personal style. If your area is cold, you’ll also want an extra outer layer. Find a blazer or long coat that complements your height and pairs well with the dress and shoes. For a more fashion-forward look, try a cropped jacket with another layer that falls right above your knees.

Everyday Winter Outfit

This winter outfit is perfect for running errands or sipping a warm drink in a coffee shop. It’s the perfect balance of casual and easy, but is coordinated enough to look intentionally styled. Start with a fleece or sweater layer in a fun print or solid color and match a puffy vest or coat to ensure that you’ll be ultra comfy and warm. On the bottom, wear your favorite denim jeans and the faithful Mini Uggs that are trending right now. You’ll be aligned with the current styles without having to overexert yourself or your wardrobe. Top the look with a beanie and you’re ready to walk out the door.

Cool & Casual

A pair of jeans in a dark wash is easy to elevate with other items, making a wintery look with items you likely already have at home. Wear the denim bottoms with a slim bodysuit to keep the look balanced. Style this outfit for a night out, a casual after-work event, or casual hangouts by wearing a heeled boot, a puffer jacket, and sunglasses.

Dress-y In The Winter

Dresses should still be in your rotation during the winter season, so don’t think about storing them away just yet. Consider your little black dress, sweater dresses, and skirts key players in your winter wardrobe. Again, layers-on-layers will keep you warm and fashionable.

Floral Dress & Sweater Combo

Shop: Dress | Cardigan | Bag | Necklace | Boots

We are all about making your wardrobe as versatile and sustainable as possible. A floral dress is yet another staple item during the warmer parts of the year, but you can easily make it into a winter outfit. Pair a cozy sweater with the dress on top, giving the illusion that it is actually a skirt. Or, simply add a cropped cardigan to break up the long line of the dress and provide the extra warmth that you need during the colder months. After that, it’s all about easy accessories! These lace up boots give a casual-cool vibe to your outfit and an initial necklace gives the look a personalized touch.

Long Dresses (And Layers)

Monochrome looks make for a chic, yet simple winter outfit, especially when it’s all black. A heavy coat is a winter must-have when layered over an oversized tunic or long sweater dress. Since the look itself is so simple, this is a great time to play with a unique patterned tight. Converse make sure that the look isn’t too dressy, and these black or white sneakers are a huge trend for fall and winter outfits. Top it off with your favorite accessories (you can never go wrong with a black crossbody bag) and this is a ‘fit that is effortlessly cool.

Turtleneck Dress

Shop: Coat | Dress | Boots | Sunglasses | Bag

A long wool coat is the ultimate staple in any daily wardrobe. An oversized turtleneck sweater dress provides an extra layer of cozy warmth. The winter often means lots of snow, so a pair of knee-high boots will keep your feet and legs protected against the cold. If you’re feeling brave, wear this look without tights, however, we’re leaning into a pair of fleece-lined tights to make sure our legs stay extra warm. These retro sunglasses are giving us all the Hailey Beiber vibes.

Fancy Winter Outfits

For the winter evenings that you want to show out! Maybe you have a winter wedding or upscale holiday party on the books, these outfits will be perfect for these winter soirees. There’s a way to wear winter glam without overdoing it.

(Wrap) Coat And (Wrap) Sweater Dress

Shop: Coat | Dress | Heels | Mini Bag | Bracelets

A festive way to upgrade a winter outfit is to include rich, textured fabrics—such as suede or wool—as they can elevate any outfit. Pair this long coat with a sweater wrap dress for extra warmth and coverage. Style with sheer black tights if you want to add yet another layer. If you’re looking for an opportunity to wear heels this winter season, this fancy outfit is calling your name more than ever!

Silk Slip Dress

A silk slip dress of any color can be a key player in your winter wardrobe. It doesn’t have to be saved for spring or summer, so wear it to your next holiday party. Depending on the attire for the event, style the dress with pumps, patterned tights, and a cashmere scarf. If the weather asks for it, wear a pair of gloves as a chic, yet useful accessory. Lastly, grab your winter coat and adorn your ears with ear-hugging hoops. You’ll be ready to step out for your fancy winter event in no time!

New Year’s Eve Ready Sequined Dress

Shop: Sequined Dress | Faux Fur Jacket | Pumps | Clutch | Earrings

This winter outfit is far from business casual and meant for you to shine and sparkle! If you’re in the mood to be festive, wear a glittery, sequined mini dress to your next holiday party. Pair it with your favorite faux fur coat and patent pumps for shine. If you want to dress it down, you can wear your favorite flats or platform boots for an edgier, but effortlessly cool outfit. Top it off with a shimmery lip gloss to tie this unforgettable winter look altogether. Maybe you’ll save it for a fun New Year’s Eve party, but this outfit will make you want to dance all night.

Holidays With The Family

Holidays with the family are meant to be comfortable and cozy. However, there’s a high chance your photos will be taken, too—maybe more than you’d like. There’s no harm in wanting to be picture-ready! These outfits are ultra-comfortable to lounge in, but will make sure you’re dressed well for all the possible photo ops.

Oversized Cardigan With Leggings

Pull out your favorite oversized sweater for a cozy family holiday gathering. Wear a basic pair of black leggings or dress up a bit more with a faux leather pair. Comfort is a priority, especially when you’re spending time in the family living room, which might mean a lot of sitting and chatting with a warm beverage in hand. Feeling extra merry? Wear a pair of holiday-themed earrings, such as a North Star, mistletoe, or even cute ornaments. Lastly, wear your favorite sneakers to keep the outfit casual and cool.

Relaxed Dark Monochromatic

We’re not sure how your family celebrates during the holidays, but we like to relax, so wearing comfortable and loose clothing is a must for us during the holidays at home. Wear your favorite pair of pants and a cotton tank for an easy, put-together winter outfit. Style it with chunky boots to elevate the look and be ready for any full-body photos with your loved ones. (Plus, we love a dark, monochromatic color palette!)

Jeans With A Festive Touch

If you’re not into trousers and want to keep it casual with denim when with the family—wear your stretchiest pair of jeans. Whatever wash you decide to rock, pair it with a cropped cardigan, simple tee, and festive earrings. Try bold statement earrings, such as red, deep green, and metallics. Don’t forget your winter boots! This is an ideal “last-minute” outfit that you can easily put together with what you already have in your closet!

Holiday Graphic Sweater

For the extra-casual holiday gathering with the family, wear a holiday-themed graphic sweatshirt with light wash jeans. The graphic top options are endless, so pick one that matches your style (or your favorite Christmas movie). Lastly, stay warm with your favorite beanie, put on your go-to boots, and accessorize with a pair of gold hoops. You will be comfortable and fashionable while lounging with the family without overdoing it!

Ugly Christmas Sweater Party

Okay, so there might not be anything in this outfit that screams “wearing on repeat” but is it the Christmas holiday season without at least one party? If you’re throwing an Ugly Christmas Sweater Party, you know that the goal is to find the most outlandish ensemble imaginable. So, why not mix it up by adding in a Christmas bulb necklace and tree fringe earrings? Add to the whimsy, we say!