17 Cool, Casual Work Outfits to Wear All Winter Long

Updated 11/02/18

Now that summer’s over, you don’t have to worry about sweating through your clothes during your morning commute. Yet 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 work-appropriate winter ensembles on hand is always a good idea. Read on to see our favorite work outfits that anyone can put together in minutes.

Easy outfit for work

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

Violeta Check Unstructured Blazer $100

Every working woman should have a check blazer.

Le Nouveau Cropped Mid-rise Straight-leg Jeans
Frame Le Nouveau Cropped Mid-Rise Straight-Leg Jeans $235

Perfect for casual Friday.

What to wear to work in the winter

A deep-hued sweater with a wool skirt will look so chic.

& Other Stories Relaxed Fit Cashmere Sweater $169

Classic for a reason.

Redvalentino - Houndstooth Wool Blend Mini Skirt - Womens - Camel
RedValentino Houndstooth Wool Blend Mini Skirt $350

Style this with tights and over-the-knee boots.

Simple work outfit for winter

Add some color to your winter wardrobe with a royal-blue sweater.

Cutout Ribbed Wool And Cashmere-blend Turtleneck Sweater
Antonio Berardi Wool and Cashmere-Blend Turtleneck $1595

This color is so good.

Farrah Skinny
AG Farrah Skinny $178

Can’t go wrong with classic black skinnies.

Casual work outfits for winter

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

ASOS Knitted Cardigan in Brushed Yarn
ASOS Knitted Cardigan $40 $20

This color is perfect for fall.

Women's Plus Size Seamed Asymmetric Hem Slip Skirt - Who What Wear™
Who What Wear Seamed Asymmetric Hem Slip Skirt $33

Wear this all season long.

Over the knee boots work outfit for winter

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

Cashmere Cable Sweater
Ryan Roche Cashmere Cable Sweater $995

Ryan Roche makes some of the best knits out there.

Loko smooth-leather knee-high boots
Isabel Marant Loko Smooth-Leather Knee-High Boots $1175 $470

You’ll love wearing these.

Winter work outfit with pleated skirt and blazer

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

ASOS DESIGN Curve mix & match tailored blazer
ASOS Curve Mix & Match Tailored Blazer $64

No such thing as too many blazers.

Pleated Draped Plaid Midi Skirt
Vince Pleated Draped Plaid Midi Skirt $395

Pleated skirts are always welcome at the office.

Winter work outfit with green blazer

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

Jaira Cable-knit Wool Turtleneck Sweater
Vanessa Bruno Jaira Cable-Knit Wool Turtleneck Sweater $455

This asymmetric sweater is perfect for the chilly weather.

Helena Cropped Distressed Mid-rise Straight-leg Jeans
Grlfrnd Helena Cropped Distressed Mid-Rise Straight-Leg Jeans $230

These are so flattering.

Puffer coat work outfit for winter

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

Hide Vegan Leather Puffer Coat in Black
Nanushka Hide Vegan Leather Puffer Coat $625

This puffer is a fashion girl favorite.

Violeta Houndstooth Trousers $60

Wear these with loafers for a more relaxed ensemble.

Easy winter work outfit with sweater
Style Stalker

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

Cropped Open-back Cotton And Cashmere-blend Sweater
Victor Glemaud Cropped Open-Back Cotton and Cashmere-Blend Sweater $325 $98

Just wait until you see the back.

Wool-blend pants
Joseph Wool-Blend Pants $350

Perfect for those colder offices.

Yellow sweater blue skirt work outfit
Style Stalker

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

crew neck sweater
Moncler Crew Neck Sweater $535

This will brighten up anyone’s day.

draped front leather skirt
Saint Laurent Draped Front Leather Skirt $413

Add a pop of color to your outfit with this skirt.

Neutral winter work outfit
Style Stalker

Wear your paperbag pants for the winter with a cool neutral colorblock sweater.

Lofty Colorblock Sweater
3.1 Phillip Lim Lofty Colorblock Sweater $395

So cute.

Mora Suiting Stella Wide Leg Paperbag Pants with Removable Belt
Tibi Mora Suiting Stella Wide Leg Paperbag Pants $550

We’ll always love Tibi for the office.

Casual winter work outfit with fur coat
Style Stalker

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

Cropped Faux Fur Jacket
Blank Denim Cropped Faux Fur Jacket $98

Every fashion lover needs a chic faux-fur jacket.

Women's Rag & Bone/jean Bella Flare Jeans
Rag & Bone Bella Flare Jeans $225

Wear these with boots or heels for the office.

Easy winter work outfit with plaid blouse
Style Stalker

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

Beaufille Cupra Tie Neck Blouse $645

Vintage vibes get a modern upgrade.

Linen Wide-leg Pants
Mansur Gavriel Linen Wide-Leg Pants $565

These are essential, no?

These cool, casual work outfits will make getting ready a breeze, even in the dead of winter.

These cool, casual work outfits will make getting ready a breeze, even in the dead of winter.

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