In the wintertime, weather conditions aren’t always ideal for wearing heels. The ground gets wet and slushy and temperatures drop below freezing, making walking in anything void of traction risky business. But wearing heels in the winter is still enticing, so what’s the best way to do so? According to fashion stylist and style expert Naina Singla, the key to wearing heels in the winter is to do so safely, and that means scouting out styles that can handle whatever the day’s forecast has in store.
“The key is to have a stable base, so a chunky boot, wedge, or block heel are going to be your best options,” Singla says. “If you're deciding between stilettos and boots, I always recommend ankle boots and tall boots with a low heel (2" or less). In contrast to high heels, lower-heeled shoes will keep you warmer and safer.” Bottom line: The best way to wear heels in the winter is to pick out a style you can walk in, safely.
The goal is to feel as good and comfortable as you look, so we’ve rounded up some of the best options for the season.
The kitten style is an excellent winter heel option for a few reasons. First, kitten heels are short heels; because they’re low to the ground, your sole has more control over your shoe, making it easier to walk. You can also find the occasional kitten heel with a chunkier heel, so you’ll have a bit more traction crossing streets and traveling up sidewalks.
Pair them with a dress or skirt, hosiery or thick tights on warmer winter mornings, or high-waisted trousers and a cozy sweater.
What we love about this chunky shoe is that it’s versatile. You can wear them with knee-high socks and a skirt or skort to channel dark academia vibes or use a pair to elevate a simple jeans and t-shirt combo. The benefit to wearing platform loafers that act as a pseudo-heel is that the lift doesn’t come from one end of the shoe; it’s raised all away across, so you score added height without risking your balance on a slippery sidewalk.
Chunky Combat Boots
Fashion intersects function in a combat boot. This type of footwear was made for harsh weather conditions, as it’s sturdy—made from materials like rubber, nylon, and leather—and waterproof. Though commonly worn with pants, they also pair well with leggings and tights, adding an element of edge to feminine silhouettes like dresses and pleated skirts.
Over-the-knee boots are the best of both worlds when it comes to winter heels. They come in varying lengths, so you can score a pair that snakes up the thigh if you’d like, offering you not only a fashion-forward style but a shoe that doubles as an extra layer of warmth for a good portion of your leg. On slightly warmer days, pairing them with a mini skirt is always an option, but we love how this style streamlines a maxi skirt or dress moment. We’d even go as far as pairing them with roomy trousers to save our skin from a frigid draft.
While knee-high boots don’t offer quite the same amount of coverage as over-the-knee boots, they’re still another great option for winter heels because you can find pairs made from durable materials and styles that boast chunkier block heels for optimal support. Though also highly versatile, our favorite way to style knee-high-heeled boots is with a pair of skinny jeans, a chunky knit sweater, and a long overcoat.
You might assume stilettos are a no-go in the winter, but, don’t forget, there are no rules in fashion—just precautions. We don’t advise donning inches-high stilettos if your daily commute involves a lot of walking, but our most trusted pairs are still in rotation for date nights and special occasions. The extra height elongates legs in dress pants and trousers, but if you’d rather flaunt your footwear, fashion influencer Yoyo Cao (photographed here) makes a strong case for wearing a mini dress with matching tights. This way, your shoes are displayed, and you’re still covered up from the cold. Just add a fuzzy overcoat for additional coverage.
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