A Step Above: The 2025 Oprah Daily Footwear O-Wards

We poured our soles into finding the very best flats, sandals, heels, wedges, sneakers, and more. Comfy, supportive, and stylish—those were our criteria, and these pairs passed with flying colors.

By The Editors

 

 

Our feet are our foundation. Not only do they keep us grounded, but if they’re happy, we’re happy. “The right shoe can help align your ankles, knees, hip, back, and neck joints,” says Jackie Sutera, MD, a doctor of podiatric medicine and member of the innovation lab at Vionic, a footwear brand specializing in plantar fasciitis and other issues. “Proper shoes help the entire skeleton.”

This is why we are thrilled to present our first annual Footwear O-Wards—42 stylish pairs of shoes that will keep you firmly planted in your comfort zone, because pain is never cute. Our winners include sneakers, sandals, slides, and loafers—and even high heels that make you feel like you’re walking on air. “People of all ages are looking for comfort these days, but these are not your grandma's orthopedic shoes,” says Oprah Daily creative director Adam Glassman. “They marry function with style.” We’ve also addressed foot concerns like plantar fasciitis and bunions, and scenarios like dressing up for work and sightseeing all day on vacation.

Across the board, Sutera explains, you must have adequate arch support. “It’s crucial for maintaining foot health, especially during extended periods of walking,” she says. “It also helps distribute weight evenly across the foot, minimizing discomfort,” and keeps you from overpronating and supinating, or bearing most of your weight on the inner or outer edges of your feet. Ultimately, she says, the right shoes keep your body in balance. All of our picks deliver.

 

First, Some Shoe Shopping Tips

The ideal pair of shoes must check three boxes. “They should fit well, suit your needs and lifestyle, and be worth the price you pay for them,” says Glassman. Quality shoes with high-tech construction and special features may cost a bit more. Make that four boxes: They should also be comfortable from the get-go. “I wouldn’t rely on a break in period,” Glassman says. If you’re shopping in a store, avoid doing so first thing in the morning. “It’s always better later in the day when your feet are a bit swollen, so you can get your best fit.” Walk around in them for at least a few minutes and pay attention to how your pressure points feel; and make sure you don’t slip. Above all, be honest with yourself about your needs, what you’ll wear them with, and how many times, he suggests. Lastly, always check the return policy, especially if you are shopping online.

 

How We Tested and Selected These Winners

“At Oprah Daily, we give our honest, expert opinions and reviews for everything we do,” says Glassman. “Since day one, we’ve considered our readers first—their needs, lifestyles, ages, how they move around in the world.” Our live-your-best-life mission involves not only bringing you goods to enhance your everyday but also making sure they’re excellent. “We like to help our readers make well-informed, relevant purchases that bring joy to their lives,” says Glassman. To determine the winners of our first inaugural Footwear Awards, editors with varying foot concerns (and dreams) walked the walk-in sneakers, flats, sandals, pumps, and booties. We logged our neighborhood strolls, weekend runs, high-octane gym sessions, and full days in heels. We tested shoes with traction on a range of terrains and took notes on arch support, cushioning, and sole thicknesses—all while applying our years of style expertise. Without further ado, let’s kick things off.

 


 

Elizée Adriana Platform

 

The rule for dressy shoes: “They should straddle support and style,” says Glassman. The worst heels make you feel like you’re painfully teetering on tiptoes. These beauties do the opposite. They’re made to evenly distribute the weight and pressure of your whole foot and have three tiers of cushioning embedded within for support and shock absorption. And let us not forget the elegant design: They’re versatile enough for work, dinner out, parties, you name it.

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