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

Many of you are either already back in the office or counting down the days till that time. While things seem to be “getting back to normal,” the last two years have definitely made a lasting impact on our clothing decisionsnamely, our tolerance for uncomfortable work attire. Yes, that feeling of being buttoned up at work can translate into productivity, but WFH life has shown us that it’s not absolutely necessary. Whether the CEO at your company likes it 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 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 six in the morning.

1. Skirt Suit + Sweater
Business casual winter outfits: skirt suit and sweater



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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A blazer you can wear with anything.

Shop the matching Mini Skirt ($36)

2. Shearling Jacket + Layered Knits
Business casual winter outfits: shearling jacket and layered knits


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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The kind of jacket that stays on at work because it's just that good. 

3. Tailored Vest + Trench Coat
Business casual winter outfits: tailored vest and trench coat


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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I've seen a lot of vests this season, and this is my favorite.

Here, I present to you the vintage cut and style we all dreamed of finding.

4. Knit Top + Pleated Pants
Business casual winter outfits: knit top and pleated pants



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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Ribbed sweaters have the power to make your whole look more polished.

Pinstripes can be styled punk or preppytake your pick.

5. Maxi Skirt + Blazer + Loafers
Business casual winter outfits: maxi skirt, blazer, and loafers



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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Zero clinginess in this A-line skirt so you're free to live your best life.

6. Sweaterdress + Square-Toe Boots
Business casual winter outfits: sweater dress and square-toe boots


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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Does it get any comfier? I think not.

These Miista boots are half off! A square-toe heel makes any outfit 10 times cooler.

7. Pleated Skirt + Crew-Neck
Business casual winter outfits: pleated skirt and crew-neck



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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Thick pleats like this are the move.

Layer a turtleneck underneath for added warmth.

8. Sweater + Dress
Business casual winter outfits: sweater and dress



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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This dress is styled perfectly. Add a white sweater-vest, and you're off to the races.

This cropped sweater hits at the perfect length to layer with flared and A-line dresses.

9. Maxi Dress + Blazer + Belt
Business casual winter outfits: maxi dress, blazer, and belt


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

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On Fridays, wear this blazer with a dress to seamlessly transition from day to night.

Everyone needs this dress in their closet. You'll reach for it every week.

When layering black or neutral pieces, I always look for texture to add dimension to the outfit.

10. Oversize Basics
Business casual winter outfits: oversized basics



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

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The weight of this jacket is perfect for the indoors.

11. Jumpsuit + Turtleneck
Business casual winter outfits: jumpsuit and turtleneck



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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Wear this in the winter with a sweater and in the summer with heeled sandals.

Go ahead and give yourself a hug for making it this far. You deserve it.

12. Quilted Vest + Trousers
Business casual winter outfits: quilted vest and trousers



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

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Eureka! These are the ideal length and cut. 

Don't let the finance bros dissuade you from trying on quilted vests. It's all in the styling.

13. Pencil Skirt + Long Trench
Business casual winter outfits: pencil skirt and long trench


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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OMG this is hot. Definitely wear tights underneath.

I'm partial to this shade of camel because it just as easily pairs with the light and darker colors in your closet.

14. Shacket + Loafers
Business casual winter outfits: shacket and loafers


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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I wear mine buttoned up and with brown trousers.

These classic '90s Weejuns are the perfect shape and are super affordable too. Thank me later.

15. Elevated Basics
Business casual winter outfits: elevated basics



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

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