15+ Cute Cold Weather Outfits For The Chilliest Of Days

Wondering what to wear when it’s chilly outside? You can still bundle up and look cute with these chic cold weather outfits!

collage of four women wearing stylish cold weather outfits

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Cute Cold Weather Outfits

When the warmth of summer fades and cold weather hits, you’ll need something to wear besides big puffer coats and your go-to sweatpants. Enter these super cute cold weather outfits. Up ahead, I’ve gathered my favorite functional (and fashionable) outfit ideas that will keep you chic, warm, and stylish all fall and winter long.  

No need to dread the cold weather season! These outfit ideas are sure to spark inspiration for even the dreariest winter days. 

Sporty chic.

Woman wearing leggings, a puffer coat and sneakers.

get the look:

This cold weather outfit proves you can look effortlessly chic even in athleisure. Recreate Emelie’s look by pairing your workout outfit with New Balances, long socks, and a quilted jacket. This sage green jacket is stunning, but any color will achieve the same model-off-duty aesthetic!

A slicked-back bun, handbag, and sunnies add a touch of elegance to this laid-back look. I’d wear this sporty chic outfit running errands, working from home, or picking up my post-Pilates latte.  

All bundled up.

Two women wearing jeans and coats sipping coffee outside a cafe.

get the look:

Now’s the perfect time to pull out your cutest winter accessories!

Pieces like fuzzy mittens, scarves, earmuffs, and hats will protect you from cool temperatures, harsh winds, and snow flurries while adding a stylish touch to your overall outfit. Pair these with wool coats, faux fur lined jackets, and cozy boots for a street style look you can wear out and about in cold weather.

Matching sweat suit + trench coat.

Woman wearing a grey sweat set with sneakers and a trench coat.

get the look:

A matching sweat set is the cutest (and comfiest) way to stay warm this fall and winter. In my opinion, matching sets look infinitely more put-together than separates, especially when you style them with cool accessories and thoughtful layers. 

For a casual outfit you can wear on chill weekends, picking up your go-to coffee order, or studying at school, start with a matching sweat suit you feel good in. A neutral color palette is more versatile—think gray, cream, beige, navy, and black—but a pop of color would look equally stylish!  

Take it up a notch with chunky sneakers, a trendy trucker hat, and a trench coat. The trench coat adds a sophisticated element to this low-key look, making it look like you tried much harder than you actually did!

Quilted jacket, turtleneck + Chelsea boots.

Christal wearing jeans with chelsea boots and a black puffer jacket.

get the look:

For an easy outfit to rock when the weather is a tad warmer, try this next look. Closet staples of jeans and a turtleneck sweater are simple throw-on pieces guaranteed to keep you warm and stylish. While a quilted jacket is the perfect lightweight jacket over thicker knits. Complete your cold weather outfit with a cute pair of Chelsea boots. 

The outfit above would be my go-to on crisp fall or early winter days when I’m running errands or doing outdoor activities. It’s practical but elegant—what’s not to love?

Cute in cashmere.

Woman wearing a matching sweat set with a long cardigan jacket, a grey scarf and black boots.

get the look:

If you love the idea of wearing a sweatsuit but want something more elevated, try a matching cashmere set instead. This luxe material is equal parts chic and cozy, making even a pair of sweatpants feel special!

I love this combination of a cashmere set with an oversized wool coat. Add dimension (and extra warmth) with a cashmere scarf, beanie and mid-calf boots for the perfect winter weekend outfit. You’d find me wearing this to the grocery store, on a coffee run, or for an evening movie since it’s so cozy. 

Burgundy babe.

Woman wearing jeans and a puffer coat while shoppings outside.

get the look:

I love burgundy in the colder months; it perfectly complements everyday neutrals while still spicing things up. Take notes from Francesca’s combination of casual blue jeans, an oversized white knit, practical black boots, and a chic shoulder bag. 

But The Frankie Shop burgundy quilted jacket is the star of the show—take one size up for a more dramatic fit! The pop of burgundy is *chef’s kiss* but you can achieve a similar vibe with wintery blues and greens too!

Faux fur flair.

Woman wearing oversized black jeans with a faux fur jacket and black hat.

get the look:

Look hot in the cold with a fun (faux) fur jacket! If you’re intimidated by rocking such a statement piece, take a page from Rebecca’s style book by dressing it down with casual pieces like baggy jeans and a black top. Round-toe boots make the outfit feel more laid-back, while fun accessories like a chic beret and trendy orange bag have a playful vibe. 

This look transitions perfectly from day to night, in my opinion! Making it a great outfit choice for bar hopping, trying a new restaurant, or hanging out with friends. 

Long coat, jeans + sneakers.

Woman wearing wide leg jeans with a black sweater and an oversized trench coat.

get the look:

You can’t take on cold weather without a long coat—it’s the ultimate winter wardrobe essential. In addition to being chic and warm, a long neutral coat will go with just about anything in your closet.

Throw it on over your favorite pair of jeans and sweater (or sweatshirt) for an easy everyday ‘fit. If you’re walking around the city or running errands, accessorize with chunky dad sneakers and a beanie. For a night out look, swap in some pointed-toe boots and a long-sleeve bodysuit.

The statement coat.

Christal wearing jeans with black booties and a black coat with matching scarf.

get the look:

Scarf jackets have quickly become winter’s most sought-after coat trend, and I have to say I’m a total fan! They’re the perfect statement coat, in my opinion. The built-in scarf and chic silhouette are a total game changer for making getting dressed in cold weather effortless and exciting. 

Scarf jackets make such a statement on their own, so I keep the rest of my outfit simple. Here, I’ve paired my Toteme Scarf Jacket with distressed jeans, a gray knit, and heeled boots for an outfit I can wear from day to night. 

All-black baddie.

Woman wearing black sweat pants, a black hoodie and a grey puffer vest with moon boots.

get the look:

On drizzling, gloomy days, you’ll want your cold weather outfit to be practical and comfortable. Go for matching all-black pieces that look stylish and put-together but also won’t get stained in the snow or rain. 

I love how Sam styled a casual black sweat set with chunky combat boots, trendy sunglasses, and a puffer vest for a low-key look. For a dressier all-black outfit, go for leather trousers, a knit top, and an oversized blazer instead.

Wool blazer + boots.

Woman wearing jeans, black booties and a grey oversized blazer coat.

get the look:

If your cold weather aesthetic is classic and refined, this next look is for you. A wool blazer is a winter wardrobe staple that looks gorgeous paired with a fitted mock neck top and cuffed jeans, a denim trend you can expect to see in 2024 and beyond. Western-style boots are a nice contrast to the modern, tailored ensemble. Finish off with silver jewelry and a mini bag for a high-fashion touch.

This is a stunning cold weather outfit when you don’t need a heavy coat. Wear this to the office or out for dinner and drinks. Either way, you’re guaranteed to turn heads.  

Shearling details.

Woman wearing jeans with a brown leather jacket, a tan beanie and sherpa Ugg slippers.

get the look:

If it’s freezing outside but you still want to look cute, try this next outfit idea. Start by slipping into a simple base of jeans and a sweater. From there, throw on a shearling lined leather jacket, some slouchy socks, UGG Tazz Slippers, mittens, and a beanie.

Shearling is one of those materials I look forward to wearing once winter rolls around. Not only will it keep you warm in chilly temperatures, but it’ll also add a cozy chic element to your cold weather outfits. You can keep it minimal with just the shearling jacket, but why not lean into the winter vibes by incorporating it into your accessories, too?

Puffer coat, leggings + boots.

Christal wearing leggings with a turtle neck sweater and a puffer coat.

get the look:

This next winter outfit is an easy yet stylish option you can recreate with pieces you likely already own. On cold days, you can’t go wrong with a sweater and leggings base. Winterize the look by adding a puffer jacket (this Quince one is incredible) and fur-lined combat boots. Up the ante even more with chic sunglasses and a crossbody bag. The end result is cozy, cool, and effortlessly put-together.

Oversized coat + Hunter Boots.

Woman wearing leggings with Hunter boots and an oversized puffer coat.

get the look:

Picture this: It’s a cold, rainy day when you’d rather snuggle in bed instead of getting up and dressed. The solution? A cozy outfit that’s just as comfy as it is cute. 

To pull off this look, start with a pair of high-quality black leggings thick enough to keep your legs warm. Leggings and Hunter boots are a match made in heaven, especially when it’s raining or sleeting. This timeless shoe keeps your legs dry and adds an elegant touch to casual outfits.

You can throw on either a sweatshirt or oversized knit, depending on your preference. The pièce de résistance is this super oversized puffer jacket which can act as your personal blanket as you bop around town. If it’s really cold, I’d top it off with matching gloves and a beanie, like Ekin Su did here.

Gorgeous grays.

Woman wearing jeans with a turtle neck sweater and a long goat with Birkenstocks.

get the look:

If there’s one positive thing about gloomy, overcast weather, it’s wearing a gorgeous gray outfit to match the vibe! I’m obsessed with Vanessa’s pairing of gray straight-leg jeans and a gray wool coat. The combo is oh-so-chic but will keep you warm on drizzly winter days. 

Versatile items like Birkenstock Boston Clogs and a cream turtleneck go with anything in your wardrobe and add a cool girl aesthetic. This is something I’d throw on for a day of shopping, a relaxed brunch with the girls, or anytime I want my outfit to strike the perfect balance of casual and classy.

If you loved this article of cold weather outfits, don’t miss 15+ Winter Going Out Outfits That Are Chic & Toasty!


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