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Our 12 Favorite Boots That Are Both Comfortable and Dressy
Your feet deserve better!
For the next several months, boots and coats are your wardrobe pillars. The elements can be unpredictable this time of year, so give your feet something to rely on with a supportive and stylish pair of dressy boots. When you hear the words “support” and “comfort” in relation to shoes, you might think the worst. I’m here to change that with a few of my favorite brands.
Podiatrist-turned-shoe designer Marion Parke is the mind behind one of these brands. With her extensive knowledge on the subject, Parke advised me on some key points to keep in mind when shopping. “A person with a higher arch is going to struggle to put on a pull-on boot because their foot has a fixed arch,” she says. Meanwhile, “People with flat feet, especially if they’re flexible, really need arch support.” Parke recommends a simple trick to test out any pair of shoes you’re thinking of buying. “Pick up the shoe from heel to toe, flex it, and then turn to see where the shoe bends. A shoe should only bend through the widest part of the toe box,” she says. I’m making a mental note to self.
With these tips in mind, I compiled 12 comfortable dress boots that will keep you on-trend and ready to make a fashionable feat of the winter months.
It’s so hard to narrow it down, but this might be the overall top boot everyone needs in their closet. It’s classic yet stylish and can be worn over and over again. The subtly heel elevates both yourself and your ensemble.
Sizes: 5-10
Colors: Black Venice, Vixon Vanilla
Heel height: 2 inches
As a former podiatrist, Parke takes her unique understanding of feet and biometrics, blending it with her love for fashion to create styles that are sure to be a favorite for comfort seekers.
Sizes: 35-42 EU
Colors: Dark Chocolate, Black
Heel height: 2.8 inches
Beyond the appeal of seasonless style and soft leather composition, these boots are backed by podiatrists—and associate fashion commerce editor Meg Donohue, who wrote an entire love letter to the shoe.
Sizes: 6-13
Colors: Tan, Black
Heel height: 2.7 inches
Toteme Wide Shaft Croc-Effect Leather Knee High Boots
Toteme’s boots add an effortlessly cool touch to your wardrobe. One of my coworker raves about the comfort and support of the brand’s footwear.
Sizes: 35-42 EU
Colors: Dark Brown
Heel height: 2 inches
I have a friend who always calls me for outfit approval before a night out. She never fails to ask which shoes she should wear, and my answer is always the same: “Your Marc Fishers!” These have made many journeys from the Upper East Side to the West Village, never ceasing to provide the support required to dance the night away.
Sizes: 5-12
Colors: Black, Medium Natural, Dark Brown
Heel height: 3 inches
Metropolitan elegance takes form in these calfskin leather boots from Parisian designer Roger Vivier. As long as I’ve worked in fashion, I’ve always admired the brand’s elegance and expert craftsmanship.
Sizes: 5-12
Colors: Nero
Heel height: 3.25 inches
If I ask my friends which shoe brands they trust, Stuart Weitzman is a common denominator. Weitzman himself believes the beauty of a shoe is only solidified by its comfortability. These are also available in an over-the-knee silhouette.
Sizes: 5-12
Colors: Black, Cream
Heel height: 1.75 inches
Schutz Maryana Knee High Boots
For those hoping to add some flair to their shoe lineup, look no further. Still, these are comfortable enough that you won’t be left wondering how soon you can take them off.
Sizes: 5-11
Colors: Natural, Eggshell, Dark Chocolate, Black
Heel height: 3.5 inches
Is any shoe collection complete without a pair of red bottoms? What I love about these—beyond the soft suede and sock-like shaft that makes them easy to wear—is how versatile they are. You can wear these with anything.
Sizes: 5-11.5
Colors: Black. Grey
Heel height: 2.75 inches
Leopard is the new neutral, didn’t you know? These feature a reasonably low heel that you don’t need to be intimidated by. Concrete jungle or otherwise, the only thing getting wild will be your friends once they see these beauties.
Sizes: 5-11
Colors: 7 options
Heel height: 1.9 inches
Veronica Beard’s beloved Cecile slingback makes its bootie debut with this cap toe style. The brand focuses on creating updated classics for the multifaceted woman, and that mission is evident here.
Sizes: 6-9
Colors: Ecru/Black
Heel height: 1 inch
The Row Zipped Ankle Boots
Every item from The Row is like a pot of gold at the end of a very elusive, secretive, no-phones-at-the-fashion show rainbow. I love that these boots are dressy AND flat, as does senior fashion commerce editor Dale Arden Chong, who counts them among her most-worn shoes.
Sizes: 35-42 EU
Colors: Black
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