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Home » Are These Oprah-Owned Ankle Boots Actually Comfy? My Honest Thoughts
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Are These Oprah-Owned Ankle Boots Actually Comfy? My Honest Thoughts

News RoomBy News RoomFebruary 3, 2026No Comments5 Mins Read
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When Oprah recommends something, it’s always a good idea to listen. But when Oprah wears something herself, we take notice. So when the 71-year-old lifestyle mogul was spotted wearing a pair of ankle boots from orthopedic-friendly shoe brand, Vivaia, in multiple colors last year, I took an interest.

Truth be told, I haven’t had a solid pair of heels in my closet since college. I prioritize comfort and casual vibes above all else, even though my 5’3” frame could use a literal pick-me-up, but the Oprah-worn Vivaia Regina Pro Boots, which feature a heel just above two inches, claim to boast sneaker-like comfort and zero break-in time. Not only that, but they’re also said to repel water, thus offering a chic alternative to rubber rain boots and bulky snow shoes. But did they live up to their claims? I decided to put them to the test.

Before you join the Vivaia hype and add the trendy footwear to your cart, be sure to read my full review of the Regina Pro Boots below.

VIVAIA Regina Pro Boots

Features at a Glance

Sizes 5-11
Heel 2.17”
Material Knit, sock-like shaft, rubber outsole
Cushion Moderate

How I tested

I threw on the Regina boots a handful of times over two weeks, testing how they fared for walking throughout the day. I missed the chance to try them out on a rainy day, so I performed an at-home test under the faucet to see if their water-repellant claims truly held out.

What I like

First things first, I appreciate that the brand uses recycled and eco-friendly materials for all their footwear. I also love the shape and construction of the boot, from its super light weight to the square-toe and futuristic sculpted block heel. It’s sleek and modern—like the Balenciaga sock boot at a fraction of the price—and the stretchy shaft and pull tabs make it effortless to throw on and take off.

footwear featuring stylish gray socks and a block heel on a textured surface

Courtesy of Michele Ross

casual outfit featuring green cargo pants and gray socks with heels on wooden floor

Courtesy of Michele Ross

I was nervous to venture back into heel territory after so long, but the Regina Boots really are as comfortable and stable as they claim to be in this regard. This is largely thanks to its cushioned insole, the extra-wide heel, and anti-slip rubber outsoles. In addition, my arches feel supported, my feet didn’t ache by the time I slipped them off in the evening, and the heel height really does feel accessible enough for day-to-night wear. Overall, I’d say that this venture back into wearing heels was a lot less intimidating (and much cozier) than I expected. For reference, my shoe size varies from 6.5 to 7, and I ended up ordering the 7 to avoid feeling too pinched. I made the right choice, so I’d recommend sizing up.

Last but not least, I held one boot under the faucet for 30 seconds to check out the water-repelling capabilities. The splashes really did bounce right off. After feeling both boots a minute later, I couldn’t discern any differences in moisture between the two. Given these results, I wouldn’t shy away from wearing the Regina Boots when I want to feel a bit fancy the next time a storm hits.

water being tested on a grey socklike shoe

Courtesy of Michele Ross

What I don’t

My feet are on the wider side, and these shoes do not come in a wide width, so they did feel a tad constricting on the first wear. Because they are made of such a comfy stretch knit, I wouldn’t rule them out completely for my fellow wide-footed folks (especially since the square toe box was so spacious!), but I did feel like the claim for zero break-in time was not true, for me at least.

I also wanted to go for the all-black boot so it’d be as versatile as possible. Unfortunately, they were sold out of this colorway in my size, which was disappointing. (I thought this could be attributed to ordering them during the holiday season; however, they’re still unavailable a month into the new year.) While I do like the glitz and sparkle of my silvery grey boots, they’re a bit less practical for daytime and year-round wear. At the time of writing, I see that there are a lot of unavailable sizes across several colors—due to several colorways going on sale on the brand’s website). Unless you’re luckier than I was, you may have to wait to place your order.

The bottom line

I didn’t expect to like the Vivaia Regina Boots as much as I did. I’m grateful I had the opportunity to test them, as it made me realize that not all heels are treated equally. The Vivaia Regina Boots aren’t only versatile enough for day-to-night wear, but they’re actually comfortable—maybe not quite as much as a sneaker, but definitely more so than pretty much any other heel I’ve owned before. They offer a modest amount of height and elevate casual outfits, so I’ll continue to turn to them, rain or shine, when I want a little something extra for my standard outfits. Per usual, Oprah knows best.

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Headshot of Michele Ross

Michele Ross is a freelance writer of 10+ years specializing in wellness, beauty, and culture. Her work has appeared in Coveteur, Editorialist, GQ, Marie Claire, Oprah Daily, Popsugar, SELF, Teen Vogue, VICE, and Well+Good, among others. She’s also crafted editorial content for brands including HUM Nutrition, Jones Road, Moon Juice, and Peloton. She’s grateful to cover her many interests, including but not limited to self-care, self-development, skincare, and Korean culture. Ever the wanderer, Michele is currently a digital nomad by way of LA, Tel Aviv, and NYC.

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