8 Stylish Winter Work Outfits For Women

December 8, 2023

As soon as the temperature outside drops past the point of comfort, people get confused about how to look polished for work. They want to have stylish winter work outfits, but they also want to stay warm.

So how do you strike that balance between not freezing and still looking professional?

Cozy up and read on for our best tips and examples for giving your winter wardrobe a raise.

3 Tips for Creating Winter Office Outfits (With Examples)

Let’s start with our style building blocks. For winter and cold weather professional dressing, you should always:

  1. Stock up on the basics
  2. Lighten up your layers
  3. Protect your ankles

Let’s explore each of these tips a little deeper.

1. Stock Up on the Basics

Stock up on basics

The NLW style team has been in the fashion industry for over 20 years. In that time, one of the biggest problems we’ve seen with clients is overbuying.

Sure, this happens year-round. People don’t know what clothes they should have in their closet so they overcompensate by buying too much.

However, overbuying happens even more when the seasons change and when the weather turns cold. 

Think about it, you want to bundle up— excuse number one to buy more clothes

Holidays and sales? There’s your second excuse to hit the shops again. 

However, you can avoid wasting your time and money this time of year (and always) by having the essentials in your closet.

This is a core principle of the NLW Style System. No matter the season, if you have these wardrobe staples, then you have a solid style foundation.

Good staples to have are:

  • A pair of dark wash jeans (Avoid distressing and opt for a slim, straight, or wide-leg silhouette for a modern feel.)
  • Trousers in core colors (black, grey, navy blue, and white).
  • A white tee
  • Long sleeve basic knits also in core colors
  • White or neutral sneakers 
  • Brown or black boots
  • A cardigan or soft-knit blazer
  • A wool (or wool-like) winter coat

Of course, you can add to this and personalize it based on your lifestyle and needs. But these are must-haves that go with everything. Having these will set your winter business casual outfits up for success.

2. Lighten Up Your Layers

The second biggest issue around winter work outfits is that women often don’t know how to layer correctly. 

So many people think that if you dress warm, you have to look bulky and broad.


The key is to start with a thin layer and build up in thickness.

The picture above is a great example of what we mean. 

NLW founder Cassandra Sethi kicks off this outfit with a lightweight knit turtleneck tucked into her trousers.

(The tuck-in is important! Without it, the outfit looks sloppy. Tucking in your shirt helps your ensemble look like you took the time to style yourself instead of just throwing pieces on.)

Then on top of that goes a Cashmere cardigan. 

Stylists love cashmere because it’s a sort of wonder material. It’s extremely soft and warm while still being durable and lightweight. That means you can cozy up without looking like the abominable snowman.

Last but not least comes the thickest layer: a sturdy coat. In this picture, Cassandra went for a wool coat. Like cashmere, it’s great for keeping warm and layering up while still looking polished. 

She also went for a simple, clean-cut style to maintain that polished vibe. 

So to refresh:

Base layer = lightweight knit

Mid layer = mediumweight sweater

Outer layer = Thick or heavyweight coat

It’s that simple!

3. Protect Your Ankles

Protect your ankles

One of our biggest winter pet peeves? That feeling when an icy winter wind hits your ankles. 

You’ve bundled up the rest of you, so why leave your ankles out in the cold?

Cropped pants are a popular style for women’s workwear. But once winter hits, people don’t know how to style these. So they either avoid them altogether, or they take the hit and deal with the discomfort.

The answer is simple: socks. 

If you’re worried about if they’ll look funny peeking out from your outfit, follow this rule of thumb.

Always match your sock color to your pants or your shoes. Grey pants? Grey socks. Black shoes? Black socks. It doesn’t have to be an exact match, just something in the same color family keeps your look cohesive.

And here’s another tip: boots are the ultimate winter business casual shoe

Don’t limit yourself to only heels, flats, or sneakers – especially if you live somewhere with constant rain and snow.

Chelsea boots, for example, are a stylish, yet classic option that won’t have you slipping on ice, freezing your ankles off, or looking unprofessional.

A Few of Our Favorite Women’s Winter Work Outfits (and Where to Where Them)

You’ve got your building blocks, now let’s put them into action! Here are five more winter outfits for women that we love. 

We’ll break down why these work, and where to wear them.

1. Belt It Out

Why it works: 

A skirt or dress paired with a blazer is a fun way to make business wear your own. It balances softness with structure.

But what’s really key to this look is the belt. The belt ties it together (literally) and gives this ensemble some shape. Without the belt, it’d be easy for this to look messy.

To make this look even more winter-ready add on tall leather boots to protect your legs and ankles while looking chic. Remember, winter office outfits should be functional too.

Where to wear it: 

Formal events (like a holiday party) or an evening out.

2. Snuggle Up in a Skirt

Why it works: 

You can get all the cozy vibes of a sweater without resorting to sweats. A great way to do this is with a knit skirt. 

You could wear this skirt as a set as shown above, or opt for a tucked-in blouse for a little more definition.

Where to wear it:

Business casual or casual occasions.

3. Chill Out in Chocolate

Why it works: 

Monochrome is a year-round outfit formula. Wearing the same color-head-to-toe is an easy way to hack finding separates that match.

BUT you can level up by mixing in different shades and textures of that same color. 

We also love the rich tans and chocolates to make this look feel more modern.

Last but not least, this look is as practical as it is stylish. Notice the turtleneck under the button-down for extra warmth. 

You could easily transition this into a spring look by removing the turtleneck later in the year.

Where to wear it: 

Formal or business casual dress codes.

4. Make a Pattern Power Play

Why it works: 

Don’t worry, we’re not just about neutrals and monochromes for winter office outfits. Patterns and prints are part of the fun of fashion!

The secret to pulling them off is pairing them with core colors, like in the picture above. That way the pattern gets to be the star of the show instead of clashing. 

Another detail that makes this ensemble a hit? The subtle texture of the pants. Textures like corduroy, velvet, and ribbed knits add that wintry, warm touch to an ordinary outfit.

Where to wear it: 

Depending on your footwear, anywhere. Sneakers make it casual, leather loafers or boots say business casual, and heels or boots upgrade it to formal.

5. Brighten Up With Winter Whites

Why it works: 

As always, we love the mixing of a soft knit with a tailored trouser. This makes for the ultimate power casual moment. 

But what’s the biggest reason why this is an A+ look for the season?

The color

As much as we love dark colors, they tend to dominate the wintertime.

The mark of a successful wardrobe is versatility and variety, which is why love the light color palette of this look. 

Wearing white in winter instantly freshens up your appearance. You’ll make more of a statement and stand out from the crowd without overdoing it.

Where to wear it: 

Power casual or business casual occasions. You can always make it more formal by swapping out the cardigan for a blazer.

Want to level up your winter work outfits even more? Apply for Next Level Wardrobe’s women’s styling services. Our seasoned stylists go beyond what you read on Instagram or in magazines and give you real, actual advice for changing how you dress. 

They’ll work with you one-on-one to create a customized plan and transform how you approach shopping for good.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

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Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

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