13 Cool, Casual Work Outfits to Wear All Winter Long


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Winter has its downsides, but at least you don’t have to worry about sweating through your clothes during your morning commute like warm summer months. That said, getting dressed for the office during the winter can be just as difficult. As tempting as it is to reach for your regular sweater-and-boots combo, you might find yourself in a sartorial rut sooner than you think.

Which is why we rounded up a whole batch of easy work outfits that’ll keep you feeling fresh every day this winter. Whether you work in a more casual environment or only have a few casual Fridays here and there, having simple winter ensembles that are also work-appropriate is always good to have on hand. Read on to see our favorite work outfits that anyone can put together in minutes.


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You can’t go wrong with a casual blazer-and-jeans combination. Add a sweater when you need extra warmth.


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Don’t be afraid to combine unexpected colors like green and orange together.


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Yes, you can wear over-the-knee boots to work. Just style them with a chunky sweater and black skinny jeans.


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You’ll never go wrong with a long pleated skirt and a blazer.


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A turtleneck under a bright blazer will be so unexpected during the winter.


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Haven’t you heard? Mary Janes are the It shoes right now. Here, our Senior News Editor Erin Fitzpatrick wears hers with an oversized blazer and jeans. 


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We can’t say no to a warm puffer coat and plaid pants.


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Style a cool cropped sweater with a pair of high-waisted trousers for the office.


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A warm, oversize sweater will look so good with a bright leather skirt.


(Image credit: Style Stalker)

Wear your paper-bag pants for the winter with a cool neutral color-block sweater.


(Image credit: Style Stalker)

An oversize sweater with a lace midi skirt is always a good idea.


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A faux-fur coat and flared pants will look so cool at the office.


(Image credit: Style Stalker)

A chic plaid top will look so good with a pair of wide-leg pants for the winter.

Next, Jessica Biel wore ankle boots in the unexpected color we need for 2020.

Dale Arden Chong