Comfy, Cozy and Chic: 6 Stylish Orthopedic Shoes to Wear During the Holidays

Between the cold temperatures and inclement weather, winter is really tough on your feet. It may seem like an impossible quest to find shoes that keep your feet warm, offer the support you need and still look fashionable enough for holiday parties. But don’t give up yet because we’ve done the work for you and rounded up six of the most stylish orthopedic shoes on the market that are perfect for the winter months.

Vionic Women's Joy Jolene Ankle Boot

1. Vionic Women's Joy Jolene Ankle Boot

Whether you’re shopping for Christmas presents, attending a work party or toasting in the new year with friends, short boots go with every winter occasion. These stylish Vionic ankle boots feature a water-resistant leather upper that comes in both brown and black. The exposed zipper on the side with a sharp-looking pull offers a nice design touch while still remaining versatile. The zipper also makes it easy to take the shoe on and off, as well as swap out the removable microfiber wrapped EVA footbed. If you prefer a suede upper, be sure to check out the Serena ankle boot as well, which offers a similar design.

2. Dr. Comfort Women's Cara Casual Comfort Boots

If you’re searching for a more casual winter bootie without a heel, look no further than suede shoes from Dr. Comfort. The large toe box gives you plenty of room to move while offering protection, and a firm heel counter provides extra lateral and medial support. The insoles are removable, so you can swap them out for your own custom orthotics if you want. However, the factory insole itself is very supportive, combining a cushy polyurethane layer with gel pods in the heel and forefoot and polyethylene cushioning. The shoe also comes in medium, wide and extra wide widths for superior comfort.

Revere Women's Rhodes Ballet Slip-On

3. Revere Women's Rhodes Ballet Slip-On

Ditch the heels and wear these cute ballet flats to the office holiday party instead. You’ll still look great and your feet will thank you for it. Choose from a solid cognac leather, an onyx suede with a snakeskin patterned toe or a black or champagne leather with tasteful diamond cutouts. Each style offers a slip-resistant outsole and soft leather uppers that won’t chafe or rub. The foot bed comes with a 3mm filler that can be used to further customize the fit, or you can remove the insert entirely and replace it with custom orthotics of your choice.

4. Dr. Comfort Men's Ruk Dress Boots

Ladies aren’t the only ones who need a pair of versatile boots for the winter—and these Ruk dress boots deliver for the guys. This chukka boot style is lightweight and versatile, and will look at home at the office, the store or a party. The leather and suede material help regulate heat, keeping your feet cool and dry. The sturdy toe box protects your feet while offering plenty of room to move, and the lightweight outsole provides a skid-resistant finish. The shoe’s construction also provides extra medial and lateral support and stability for day-to-day activities.

Orthofeet Men's Highline Boots

5. Orthofeet Men's Highline Boots


These substantial boots will protect your feet from the elements during a tough winter while still looking and feeling stylish. The Highline boots unite a soft genuine leather exterior with a seamless, breathable lining on the inside. The shoe upper is padded with foam, with extra padding on the tongue and collar for added comfort. The ½-inch heel height (the difference between heel and forefoot) promotes proper walking and standing posture, while the thick sole absorbs shocks and cushions your foot. For superior fit, the shoe is also constructed on an anatomical last, with extra width across the midfoot and toe-box.

6. Apex Men's Black Ariya Moc Toe Oxford Casual Shoes

If you need a versatile pair of men’s dress shoes instead of boots, these Moc Toe Oxford Casual Shoes from Apex just might fit the bill. The more casual style won’t look out of place at a house party or a shopping trip, but it’s also appropriate for the office as colder days set in. As with all Apex shoes, these oxfords incorporate Apex's patented Mozaic Customization Technology for superior customized comfort and pressure relief. The full grain leather uppers and polyester/leather linings transfer moisture to keep feet happy, healthy and dry.
You can’t go wrong with a pair of these stylish orthopedic shoes for winter—but if none of them fits your needs, you can keep browsing our collections of the most comfortable dress shoes for women and men.

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