Keep It Cozy This Winter With These 15 Comfy Business-Casual Outfits

Whether it's the Hailey Bieber oversize-blazer effect or the fact that working from home is more commonplace than not, our definition of business clothing has shifted dramatically over the last few years. CEO approved or not, the interpretation of business casual has expanded to include cozy and comfortable pieces like leather, jumpsuits, and even sneakers. This means your weekend winter clothes and your work clothes no longer have to be stored in different drawers—it’s all game.

Below, you’ll find 15 business-casual outfit combinations to inspire you through the next several months of winter. Most of the pieces included can also be mixed and matched seamlessly, which is a dream at 6 in the morning.


1. Skirt Suit + Sweater
(Image credit: @aimeesong)

Skirt suits will forever remind me of Clueless, and for that reason, I'm eternally sold on the look. Pair yours with a sweater and button-down for extra warmth.

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2. Shearling Jacket + Layered Knits
(Image credit: @erinoffduty)

When layering knits, stick to the same color family, and you're golden. Add a shearling jacket on top, and you might as well be in Miami.

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3. Tailored Vest + Trench Coat
(Image credit: @torivanbreugel)

Tailored vests are having a moment—as are leather trenches. The two worn together look cool enough to wear to any event you have planned after work.

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4. Knit Top + Pleated Pants
(Image credit: @jaimeridge)

Pleated pants are my go-to business-casual style this year. The menswear-inspired cut is both relaxed and elevated. It's rare you see work pants in the center of that Venn diagram.

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5. Maxi Skirt + Blazer + Loafers
(Image credit: @frannfyne)

Maxi skirts are such a cool and unexpected choice in a work environment, mostly because they're associated with more carefree archetypes. Lately, though, maxis have been popping up in thicker materials and streamlined shapes that look work appropriate. Wear them layered with your blazers, sweaters, and button-downs, and polish off the look with a fresh pair of loafers.

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6. Sweaterdress + Square-Toe Boots
(Image credit: @monamali_)

Wake up late? A long sweaterdress is a must for all my habitually late risers. Add a pair of square-toe boots, and you'll look even more polished than your early rising co-workers.

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7. Pleated Skirt + Crew-Neck
(Image credit: @fongminliao)

I just love this outfit. Pleated skirts can either be dressed up with a blouse or down with a simple crew-neck sweater or T-shirt (as pictured).

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8. Sweater + Dress
(Image credit: @dinahansen)

Dresses are so easy to put on and go in the winter. Maximize the wearing potential of each dress by simply adding different sweaters on top. If you invest in your sweater game, you might be able to get away with wearing the same dress two to three times a week! We work smarter not harder around here.

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9. Maxi Dress + Blazer + Belt
(Image credit: @hannamw)

Leather is the newest member of the business-casual club. Let's give her the warm welcome she deserves and dress her up with a maxi dress and a waist-cinching belt.

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10. Oversize Basics
(Image credit: @stephaniebroek)

We may have the Olsen twins to thank for elevating oversize basics and making them acceptable work attire. 

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11. Jumpsuit + Turtleneck
(Image credit: @chrissyford)

Before we get too excited, not all jumpsuits are appropriate for work. Look for tailored and structured jumpsuits that approximate other tailored classics you'd wear.

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12. Quilted Vest + Trousers
(Image credit: @annaaborisovna)

Balance out the casual vibes of a quilted vest by pairing it with tailored trousers.

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13. Pencil Skirt + Long Trench
(Image credit: @msorrig)

We all have a stack of pencil skirts that we never wear because they can feel a little racy worn alone. Tone down the Jessica Rabbit energy by wearing them with a trench coat and loafers.

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14. Shacket + Loafers
(Image credit: @basicstouch)

The T-shirt-and-jeans outfit of the bunch, this one's an easy classic to repeat over and over again.

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15. Elevated Basics
(Image credit: @lindatol_)

Now that our weekend and weekday closets are married, invest in elevated basics that will work 24/7/365.

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