The Winter Outfits We’ll Be Wearing On Repeat All Season Long | Swift Wellness (2024)

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

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 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 wool coat to keep the warmth in. Finish the outfit with a canvas bag you can toss over your shoulder and weatherproof boots, like stylish Dr Martens.

Dress & Sneakers

Sweater dresses can make easy, casual winter outfits. We love a ribbed sweater dress for the added texture, especially when worn with tall socks and chunky retro sneakers. You can keep this outfit casual. yet elevated, with accessories like gold hoops or a layered necklace set. If your area is cold, you’ll also want an extra, outer layer. Find a blazer or long coat that compliments your height and layers well with the dress and comfortable sneakers. 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 working in a coffee shop. It’s a perfect balance of casual and easy, but is matched enough to look intentionally styled. Start with a fleece layer in a fun print or solid color and match a puffy vest or coat so you’ll be ultra comfy. 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 wide-leg jean in a dark wash is easy to elevate with other items, making a wintery office look with items you likely already have at home. Wear the wide-leg bottoms with a bodysuit and a structured balconette bra to keep the look balanced. Style this outfit for a night out, a 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.

Strappy Mini Dress

One of the best parts about winter is the ability to layer! A strappy mini dress is likely already in your closet and a staple during the spring and summer months. However, it doesn’t have to be hidden in the back of your closet during the cold winter months, either! Try layering a dress over a super soft turtleneck sweater. Add black tights for added warmth and your favorite pair of black booties. Add a matching crossbody bag and you’re ready to go!

Floral Dress & Sweater Combo

We are all about making your wardrobe as versatile and sustainable as possible. A floral dress is yet another staple item during the warm parts of the year, but you can make it into a winter outfit easily. Wear a cozy sweater over the top, giving the illusion that your dress is actually a skirt. After that, it’s all about easy accessories! Sneakers give a casual-cool vibe to your outfit and these round sunglasses are a wardrobe staple we have on repeat.

Oversized Tunic

Monochrome looks make for a chic, simple winter outfit, especially when it’s all black. A wool coat is a winter must-have when layered over an oversized tunic sweater. This top is long enough to take the place of a short dress and blends in with the rest of the look. 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

Who said blazers are only for business casual outfits in the office? An oversized wool blazer can double as a coat and 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 flat 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. A beanie keeps your head and ears protected in the cold and 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.

Sherpa Coat And Sweater Dress

A festive way to upgrade a winter outfit is to include faux fur! It can elevate any outfit and maybe make you feel a little “bad and boujee,” in the best way. (Let’s be real, there is nothing wrong with that.) Pair it with a turtleneck maxi dress for extra warmth and coverage. Layer with sheer black tights and lastly, wear your favorite stiletto boots. If a skinny heel isn’t your style, platform boots will do the trick. 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

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 black coat, tights, and pointy ankle boots. If you want to dress it down, you can wear your favorite flat, platform boots for an edgier, but effortlessly cool outfit. Top it off with your favorite 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.

Black Trousers & Cropped Blazer

Not in the mood to wear a dress to your next holiday party? Wear a nice pair of black trousers or dress pants instead! There are many styling options to choose from when centering your outfit around this versatile garment, but we suggest a cropped blazer and colored bodysuit. Put your hair in a sleek low bun, wear a gold choker with matching earrings, and as a final touch, put on your sharpest cat eye. This outfit is chic, and sexy, and will make you want to strut your stuff all evening!

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 platform sneakers to keep the outfit casual and cool.

Relaxed Corduroy And Turtlenecks

Not sure how your family celebrates during the holidays, but we like to eat throughout the day. There’s usually a large food spread, 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 turtleneck for an easy, put-together winter outfit. Style it with chunky loafers to elevate the look and be ready for any full-body photos with your loved ones.(Plus, we love a winter color palette!)

Jeans With A Festive Touch

If you’re not into trousers and want to keep it casual with denim with the family—wear your stretchiest pair of jeans. If you have a pair already, wear a comfortable pair of light blue jeggings. Whatever wash you decide to rock, pair it with a cropped blouse and festive earrings. Try bold statement earrings, such as red, deep green, and metallics. Don’t forget your winter coat and your favorite ankle 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