Shoes to Wear with Dresses in the Winter

Whether you choose a little black dress for a rooftop party or a flowy maxi for a summer concert, dresses have long been one of the most important staples in a woman’s wardrobe.

Come winter, though, dresses take on a different vibe. Hemlines are often longer, sleeveless numbers are shoved to the back of the closet, and fabrics shift from light and airy to luxe and lustrous. This has its own allure, but it also prompts every fashion-conscious woman to ask how to wear dresses in winter while remaining cozy and comfortable. And what shoes to wear with dresses in winter?

It may go without saying that this hinges on your personal aesthetic, the event you’re attending, and the weather. Nonetheless, this guide was designed so you can put your best foot forward—now and throughout the entire winter season.

Choosing the Right Shoes for Winter Dresses

Reaching for your softest, comfiest sneakers when the temperature dips may seem like the most natural choice in the world. And while pairing dresses with sneakers has been a chic street-style combo for decades, the look seems to work best in spring and summer. Plus, it might not be the best option for your workplace or upcoming winter soiree (and we all know that shoes can make or break an outfit).

So, let’s look at 5 of the leading winter dress trends and the shoes you might want to have in your winter wardrobe:

#1. The Sweatshirt Dress

Consider this your go-to dress for everything from Sunday brunch to running errands. The sweater dress and boot look is a classic staple when it comes to women’s winter outfits. Characterized by its long, soft sleeves and above-the-knee hemline, a sweatshirt dress provides extra warmth for those chilly but not quite frigid winter days and nights.

Pair it with:

Sweatshirt dresses are casual in nature, so your shoes can be too:

Sneakers – In this situation, sneakers definitely work, especially if you really are out running errands. Plus, shorter hemlines can contrast brilliantly with hightops and heavier, chunkier styles.

Ankle boots – Alternatively, you can dress up your sweater dress—and take it from day to night—with a stylish pair of ankle boots. The Belmont Ankle Bootie, for one, has a chic heel and a classic silhouette that balances out the sweatshirt dress’s easy-breezy look. These shoes will keep your feet warm in winter while still being exceptionally stylish.

#2. The A-Line Shirt Dress

At first glance, an A-line shirt dress might appear a little too lightweight for winter’s demands. Couple the timeless dress with fleece-lined tights, a scarf, and a beanie, however, and you might strike that perfect feeling of “warm but not overheating.” You can also choose a heavier material, like wool or denim.

Pair it with:

A-line shirt dresses are just as appropriate for a day in the office or a drink out with your colleagues. For extra warmth in the winter months, add a leather jacket or wool coat. Elevate your look by going with:

Tall boots – Don’t know how to wear knee-high boots? Tall boots can add a touch of edge or classiness, depending on the style you choose. Knee-high boots with a short heel, such as the Fallbrook Knee High Boot, combine lug moto with riding style for a cool-girl vibe. These boots also feature a rounded toe and water resistance, making them a versatile footwear option for different weather conditions. Craving a touch of elegance, without looking too overdressed? Check out the Bixby Slouchy Knee High Boots. They boast a traffic-stopping pointed-toe and super-cozy, all-over suede.

Heeled boots – Heeled boots can also elevate an A-line shirt dress just enough that the whole ensemble becomes ideal for lunch with a client or a day at the office. The Truckee Heeled Ankle Boot has a 3.25” heel that’s appropriate for dozens of settings. Even more appealing, though, is that it was built for all-day comfort and all of the elements. This includes contoured arch support, excellent traction, and weatherproof materials to withstand the colder months.

#3. The Maxi Dress

Maxi dresses are a summer staple for countless women; after all, nothing quite compares to that barely-there feel floaty frocks offer. But they’re just as comfortable when the temperature drops—that is, if you choose a winter-ready fabric like:

Cashmere
Chenille
Knit
Wool

Pair it with:

One of the benefits of maxi dresses is that they can be dialed down or up according to your accessories—and shoes play a part in this. When it comes time to pair shoes with a maxi dress, consider polishing off your look with:

Ballet flats – Ballet flats epitomize subtleness and delicacy, and look gorgeous with ankle-grazing maxi dresses. Just be sure to go with a pair of women’s flat shoes that offer protection against the winter weather.

Platform sneakers – Eager to add some height to your silhouette? Platform sneakers are genuine statement makers, and they pair exceptionally well with long maxi dresses.

Weatherproof boots – A smart pair of weather-resistant boots can look on-trend while also keeping you safe and comfortable. Capture attention by contrasting a shape-hugging maxi dress with the Lani II Lace-Up Boot, which features a water-repellent upper for rainy occasions.

#4. The Turtleneck Sweater Dress

A turtleneck sweater dress offers the best of both worlds for your winter wardrobe: the extra warmth and coziness of a high neck, long sleeves, and soft material, and a splash of sass to brighten up a dull January. This is especially true if you opt for a dress in one of winter’s hippest colors, such as:

Olive green
Chocolate brown
Burgundy
Peony pink
Eggshell

Pair it with:

If you live in an ultra-cold climate or simply want to be as content as possible when you step out for the day, you’ll probably want to slip on a pair of leggings or tights. So, what are the best shoes to wear with leggings? Try finishing your look with:

Tall boots – Tall boots exude sophistication, especially when they’re worn with an equally sophisticated turtleneck sweater dress. The Trabuco Knee High Boot is perfect for nearly any occasion. What’s more, its seam-sealed technology protects against ice, rain, and snow.

Ankle booties – Ankle booties redefine versatility: They’re made in a host of silhouettes and styles, from coquettish kitten heels to fashionable flats. Considered one of the best shoes to wear with dresses in winter, they allow you to show off a bit of a leg (and look unquestionably modern). The Bishop Ankle Boot fits the bill with its contemporary mini lug sole and 2.25” heel. Meanwhile, its shock-absorbing cushioning and deep heel cup will keep your feet happy from dawn to dusk no matter the winter weather.

#5. The Midi Dress

Happen to live in a mild climate, like San Francisco, Portland, or Charleston? You may be eyeing winter dresses that provide more coverage than your summer frocks but still let your skin breathe.

If so, a midi dress may be in your future. Defined as dresses that hit between the knee and ankle, They serve as the perfect office holiday party outfit or ensemble for a winter wedding.

Pair it with:

First things first: consider the weather. If your winters are minor at best (such as in San Diego), you may be able to get away with a pair of strappy stilettos or leather, open-toed flats. For more protection, or to play into the season, consider:

Tall wedge boots – A tall wedge boot, like the Ashland Tall Wedge Boot, offers an element of surprise to feminine, flowy midi dresses or snug, “ordered” midis (especially if they have a slit). The Ashland is also crafted for comfort with Vionic’s Vio Motion technology, complete with shock-absorbing cushioning and forefoot stability.

Loafers – Up your coolness factor with a pair of swoon-worthy loafers. The Tiburon Heeled Loafer is especially in vogue and iconic, whether you wear it with a business-casual midi dress or a romantic midi with lace details.

Tips for Dress and Shoes in Cold Weather

Sure, you may be tempted to wear your favorite heels with your winter dresses, particularly if you’re going for a more formal look. But to keep yourself safe, warm, and cozy this season, consider the following tips on pairing shoes with dresses:

Look for shoes with weather-appropriate materials – Leather and suede are two top choices for winter shoes, but you aren’t limited to just these materials. You can also go with canvas, for example, as long as the shoes are weatherproof. Some options to try: are the Uptown Sur Ankle Boot and the Aria Wedge Ankle Bootie, both of which look adorable with a sweater dress.

Prioritize tights, leggings, and socks – Tights, leggings, and/or socks are must-haves in some climates, as they’ll help keep your legs and feet dry, warm, and insulated. Just be sure to select the right material, like sweat-wicking wool, fleece, or knit—and save your cotton accessories for a sunnier season. Also when choosing between wide calf vs regular boots, choose the option that fits best with thick socks and leggings.

Slide Through the Winter Season in Style With Vionic

Winter weather often inspires our snuggliest sweatshirts and baggiest flannels. But some occasions call for a winter dress. How to wear dresses in the winter comes down to finding a pair of shoes that will ensure your comfort and security. Luckily, Vionic offers a broad array of winter-suitable styles, from weatherproof boots to wedged and heeled boots. And since all of our shoes are designed with medical knowledge and footwear science, you can rest assured that your feet will stay cozy and comfortable—no matter what winter activities you get into.

Pamper your feet this winter with Vionic. Shop our collection today.

Sources:

Vogue. 17 warm winter dresses to seize the day in.

https://www.vogue.com/slideshow/warm-winter-dresses

The New York Times. Can I wear sneakers with a dress?

https://www.nytimes.com/2022/07/01/fashion/style-sneakers.html

Refinery 29. The internet’s best winter dresses, according to warm & happy customers.

https://www.refinery29.com/en-us/winter-dresses-for-women

InStyle. 7 types of sneakers that look perfect for any dress in your closet.

https://www.instyle.com/dress-with-sneakers-8421192

Who What Wear. 6 colors I’m wearing to look on-trend this fall.

https://www.whowhatwear.com/fall-winter-color-trends-2024