Don’t forget your feet when bundling up in cozy knits and full-length pants. Choosing the right shoes for winter work is just as important as updating your wardrobe for the season—especially in cold climates like Chicago or New York, where winter is serious business.
Need help deciding what shoes make the cut?
Next Level Wardrobe’s winter shoe guide has you covered. We’ll break down the best office-ready shoe options to pair with dresses and pants and settle the debate on whether open-toe shoes are winter-appropriate.
Grab a hot coffee, and let’s dive in!
Shoes to Wear to Work in Winter
You’re not alone if you’re stumped on what shoes to wear to the office in winter. Our clients often ask us this question, confused about what’s appropriate and what’s comfortable, warm, and stylish.
The key is to consider your climate. What works for a chilly NYC winter may not work for a milder LA season.
For example, our founder, Cassandra Sethi, adapts her choices based on location. In NYC, she prioritizes boots with lug soles or high-grip treads for safety on icy streets. In LA, relaxed office dress codes make loafers and sneakers her go-to for staying warm without overdoing it.
Notice a trend? Closed-toe shoes are a winter staple, but does that mean open-toe shoes are completely off-limits? Scroll down for the answer!
Can You Wear Open-Toe Shoes in Winter?
The short answer is yes if it’s suitable for the weather.
- Cold climates
Open-toe shoes are a no-go if you live somewhere like Montreal, where you have to trudge through the snow. You don’t want to risk frostbite just for a chance to wear your favorite peep-toes.
However, if snowfall isn’t a concern but you’re still dealing with low temps, winterize your open-toe shoes with tights. This is another of my favorite tricks for staying warm and professional.
Black or nude pantyhose is a workwear staple and an easy way to layer up your legs and feet. For extra protection, try fleece-lined tights or thicker, sweater-like options. These will go great with all winter office shoes. - Warmer climates
Open-toe shoes are probably a year-round staple for you. While you don’t have to stress about frigid feet, you might want your shoes to look more winter-themed.
- Choose darker colors
Rich tones like plum, emerald, and cognac brown give your outfit that seasonal cheer without the chilly air. - Choose the right fabrication
Suede, velvet, satin, and leather are all cozy and wintery materials. Consider these fabric options when choosing shoes to wear in winter.
- Choose darker colors
Let’s clarify one thing about winter work shoes: open-toe options do not include sandals. Sandals, flip-flops, and espadrille wedges are a definite no for winter—and never appropriate for the office. Save those for beach days!
Shoes to Wear with Dresses in Winter
Oftentimes, clients feel like they have to save their dresses for warm seasons. But with a little layering and the right shoes, you can turn just about any dress into a cold-weather outfit.
Wondering what dress-and-shoes for work in winter combos you can wear?
Boots are the way to go. This is a styling trick we’ve been using with our clients a lot this year. Since boots come in so many different styles, it’s easy to find the perfect pair for any dress or skirt. Here are our top three picks:
1. Knee-high Boots
Product by MICHAEL by Michael Kors, shop here.
When you picture what shoes to wear in winter, knee-high boots likely come to mind. These are the quintessential shoe choice for cold weather.
The height makes them perfect for wearing with dresses. They’ll keep your legs warm while looking chic and put-together.
We recommend opting for a fitted silhouette, like these black ones from Michael Kors. The sleek, close-to-the-body design ensures your outfit looks streamlined rather than bulky or overdone.
You can partner these with any dress from a fitted knee-length option to a flowy maxi.
2. Chelsea Boots
Product by Rag & Bone, shop here
Chelsea boots are the next winter business shoes you need in your arsenal. They’re easy to pull on and have that classic, London-style appeal. Pick up a pair with a heel to add a little extra sophistication to your ensemble.
This style pairs well with midi skirts and feminine a-line dresses.
3. Flat Combat Boot
Product by All Saints, shop here.
We couldn’t resist placing flat combat boots on our list of must-haves. Opt for a sleek black leather pair like these boots from All Saints. We especially love these if you’re dressing to fit your personal brand and want to add edginess.
Stylist tip: Pick out minimalist combat boots to maintain a professional vibe. Avoid pairs with excessive buckles, metal eyelets, or studs.
Winter Shoes to Wear with Work Pants
Most of us choose to wear more pants during the colder months. It’s functional, easy, and warm. So of course, we had to put together a list of what winter business shoes go best with pants. Here are our 3 favorite office-approved styles:
1. Heeled Ankle Boots
Product by La Canadienne, shop here.
Say it with us: boots work with everything.
Winter calls for low-key heeled booties paired with your favorite trousers. Heeled ankle boots are the perfect solution—tall boots and pants can feel bulky, but these shorter options offer a sleek alternative. Plus, they provide just enough height to keep your ankles warm.
Going for a heel over a flat silhouette is a subtle way to elevate your outfit as well. We love these brown suede ankle boots from La Canadienne. They look toasty yet polished and professional all in one.
2. Loafers
Product by Vince, shop here.
Loafers are the best option if you live in a mild climate. This shoe is having a major resurgence right now, and we can see why.
Just take a look at the camel-colored ones above from Vince.
Loafers are a work wardrobe staple. On top of being comfortable, they look professional and have a unisex appeal.
3. Ballet Flats
Product by Chloé, shop here.
Last but not least: ballet flats. These are truly a 24/7, 365 days a year type of shoe. They’re always going to fit any office dress code.
Much like loafers, we only recommend ballet flats for mild or warm winters. If you live somewhere that gets colder than 30 degrees during the workday, stick to boots.
But if not, these black scalloped flats from Chloe are an excellent winter shoe choice.
Need professional help finding the best workwear shoes this winter?
Apply for our women’s virtual or in-person styling services. Our team of experts will reset your wardrobe and get you prepared for next winter!
