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

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

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Outfit 2

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

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Outfit 3

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

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Outfit 4

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

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Outfit 5

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

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Outfit 6

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

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Outfit 7

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

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Outfit 8

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

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Outfit 9

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

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Outfit 10

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

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