From Casual to Cocktail: 10 Winter Outfits That Look Polished Every Time

While every season has its fashion perks and downsides, I have to admit I find winter to be especially difficult to dress for. Sure, I love the luxe fabrics and the coats and the boots, but between the weather and the elements and the layering, it can sometimes feel tough to look as cool as I'd like while staying as warm as I must. Not to worry—for every problem, there's a solution.

As I do every season, I recently did a little internet sleuthing in search of chic outfits to serve as my inspiration for the months ahead. Below, you'll find 10 outfits to keep you looking chic this winter using pieces you likely already own, from legging-clad ensembles to more dressed-up outfits. Of course, if your wardrobe is lacking something or you simply want to do some shopping just because, I've got you covered there too. Just keep scrolling to get started.

Outfit 1

polished-winter-outfits-311099-1701969854567-image

(Image credit: @mcristinastyling)

Style your maxi skirt with chunky loafers and a tonal cardigan. 

Get the look:

Outfit 2

polished-winter-outfits-311099-1701969854865-image

(Image credit: @slipintostyle)

Give new life to your old shearling jacket by pairing it with leggings and matching accessories.

Get the look:

Outfit 3

polished-winter-outfits-311099-1701969853732-image

(Image credit: @anoukyve)

Keep it casual in a camel coat styled with a simple button-down, a classic belt, jeans, and loafers.

Get the look:

Outfit 4

polished-winter-outfits-311099-1701969853948-image

(Image credit: @cassklatzkow)

That maxi knit dress you wore all of fall will look even cooler with a leather trench and pumps this winter.

Get the look:

Outfit 5

polished-winter-outfits-311099-1701969854248-image

(Image credit: @emmarosestyle)

A belted blazer always looks polished, so why not style it with your favorite baggy jeans and chunky boots?

Get the look:

Outfit 6

polished-winter-outfits-311099-1701969855181-image

(Image credit: @aimeesong)

For a party dress you'll want to wear year after year, opt for a black strapless maxi and just add pumps.

Get the look:

Outfit 7

polished-winter-outfits-311099-1701969855449-image

(Image credit: @thedailydeb)

Curious about what I wear on repeat? You're looking at it. An oversize blazer with cropped pants and slingbacks will never get old. 

Get the look:

Outfit 8

polished-winter-outfits-311099-1701969854406-image

(Image credit: @honeybelleworld)

Say it with me: leggings, oversize sweater, Mary Jane flats.

Get the look:

Outfit 9

polished-winter-outfits-311099-1701969853559-image

(Image credit: @alexisforeman)

When you pair a duster coat with a balaclava and loafers, it doesn't even matter what is underneath—you'll look chic regardless.

Get the look:

Outfit 10

polished-winter-outfits-311099-1701969853088-image

(Image credit: @annelauremais)

I'm taking notes on this combination of a cable-knit sweater, a miniskirt, and flats.

Get the look:

Editor-at-Large

Since starting as an intern back in 2013, Nicole Akhtarzad Eshaghpour has held several roles here at Who What Wear, and she is currently Editor-at-Large. It was a less expected route, seeing as she was graduating from business school at USC when this all began, but it has turned out to be the best one for her. Fast-forward to 2024, and she's moved to NYC from her hometown of Beverly Hills and spends her workdays a little differently from when she was an intern starting out. Currently, she focuses on a weekly mélange of shopping content. As far as her personal style goes, she's largely drawn to classic pieces and neutral basics but will always make an exception for something colorful, printed, or bejeweled as long as it's deemed worthy enough. After all, the only thing she loves more than a good party is dressing up for one. On weekdays, she can usually be found at home eating something delicious for dinner and trying to force her husband to watch Summer House.