Looking for clothes on cold days requires a certain knack for wearing them. The Style Collection has years of practice in this department, designing cool weather looks to carry them to shows, parties, and dinners in comfort. We used their research to collect the best casual winter wear - those that truly transition from the high fashion ecosystem to everyday life. Our consensus? Cool style stands a chance of facing the doldrums of winter.

Be prepared to over-indulge on shearling, leather, and cashmere — aka those skinny fit fabrics that are easy to layer and make great insulators. There are a few trends that take a back seat, like strappy sandals and cut-out shirts, that don't stand a chance against sub-zero gusts of wind. Not to worry: Its seasonal alternatives are equally inspiring. Grooved combat boots (a la Proenza Schouler) and puffed bottoms make facing the cold even sweeter. Come spring, you will mourn their parting.

Best Casual Winter Outfits

best casual winter outfits

1- Shearling Vest & Maxi Dress

Do you have a sensual poplin dress that you'd like to transform into winter wear? Choose a fur jacket - a jacket that allows the puffy sleeves of a dress to speak for itself. Add more opulent embellishments with a pair of cow-print ankle boots and a crocodile-embossed handbag. This look is for downtown hanging and shopping.

2-  Leather Trench & Vibrant Button-Down

If a wool peacock coat isn't for you, consider replacing it with a leather trench. This Fashion Week attendee uses her guidance to channel two color trends in Winter 2021/2022: chocolate brown and kelly green. Put a button down at the bottom and finish the look with split hem pants.

3-  Fur-Trimmed Coat & Python Pants

It may seem overwhelming, but the python can be the style needed to spruce up any casual winter outfit. This guest pair combines snakeskin pants with a cropped coat. The monochrome combo will stand out against the freshly fallen snow-lined city streets.

4- Gingham Coat & Statement Heels

Gingham is a safe choice when shopping for winter coats, staying on-trend amid changing trends. Take a page out of this reviewer's book by expanding the coat palette in black and white—with Bottega Veneta's zebra heel boots.

5- Cable-Knit Scarf & Dress

Some of the best winter casual outfits are centered around knitwear. This Fashion Week attendees are creating a knitted dress with a scarf for an opulent look. Consider this formula for those days when you don't want to get out of bed. Finish it off with a pair of buttercream boots and a Loewe phone bag.

6- Scarlet Coat & Kitten Heels

Good news: *You can* wear straw bags during the colder months. To make the transition easier, pair it with a vibrant wool coat (basic colors are encouraged) and a pair of cat heels. A casual handbag transforms into a chameleon with these directional silhouettes.

7- Gabardine Coat & Cognac Ankle Boots

While gabardine coats are a favorite during fall and spring, they can easily be warmed up with the help of a duster. Wear it over a long pink button-down (in the style of James Williams' Mecca) and tie in a Wandler's Georgia bag to match. A simple layering hack accentuates the usual trench-and-shoe ensemble for casual afternoon errands.

8- Winter Whites & Chelsea Boots

Brilliant white gives casual winter clothes a sophisticated boost—even when using soft-soled shoes. Choose a milky wool coat and a matching turtle neck with the Proenza Schuller Chelsea boot, which features contrast stitching for a bold look. Don't forget to tie the neck in this beloved Staud's Moon bag.

9- Sheepskin Coat & Corduroy Pants

The '70s are back with a vengeance this season. For cooler days, team the most luxurious textures of the era with a sheepskin coat and corduroy pants, both of which bring warmth without compromising style. For a western kick, complete the look with cowboy boots and a puffed blouse.

10- Textured Puffer & Bucket Hat

Nothing eliminates the fuss of winter clothing like a down jacket. Whether you love it or hate it, bouffant coats are essential for creating casual winter wear on the go—especially on the days when you're running late and don't have time to build a layered look. Style a woven bouffant with a matching bucket hat. Sculptural silhouettes may seem overwhelming at first, but nothing a pair of cigarette pants can't balance.

11-  Shearling-Lined Moto Jacket & Jeans

Fact: Warm outerwear can be irritating. Choose this shearling brocade moto jacket for the best of both worlds. The silhouette makes a big splash on its own, so opt for blue jeans, a Chanel flap bag, and Chelsea boots to balance out the statement coat. Voilà - You have the perfect outfit for getting into vintage stores all over town.

12- Leather Bomber & Fair Isle Sweater

The bomber is often overlooked as a winter jacket, but who said a feathered leather iteration wouldn't do the trick? The duo, collaborating with a fair island jacket, will provide all the insulation needed to withstand bitter cold days. Complete the look with every New York girl's companion: clutch, Prada's Re-Nylon bag and everything.

13- Faux Fur

Faux fur is one of the best casual winter outfits! It is not necessary to look up. Short faux fur jackets tend to look sharp while midi-length coats look elegant, so choose what works best for you.

14- Wool Blazer

Wool Blazer coats are fun because they differ from common winter outerwear (jackets, puffer coats, etc.). It usually hits the middle of the thigh, which is a great length to keep warm without allowing the coat to overpower. Wear skinny jeans, a knit jacket, and loafers or sneakers.

15- Puffer Coat

For a more tailored look, try a matching puffer coat. This winter's long puffer sweater is a cashmere cardigan that falls - easy to pull off when you're running out the door. I style it with lace-up boots, faux-leather leggings, and a beanie.

16- Puffer Jacket

Oversized jackets paired with jeans and loafer boots are trending in street style. If you love this look, an easy way to wear it is with straight jeans and a relaxed jacket.