Oprah’s product recommendations have never led us astray, especially when it comes to shoes. The 71-year-old media mogul has impeccable taste in footwear, whether she’s sporting fresh running shoes in the gym or running errands in a pair of rain loafers. She’s nailed the perfect balance between style and comfort. During a taping of Oprah’s Book Club on CBS Mornings, Oprah donned a pair of Vivaia Regina Pro Block Heel Boots in a navy shade to match her pinstriped outfit. This isn’t the first time we’ve seen the lifestyle mogul step out in these shoes, either. She wore them in a caramel color back in December 2024 for a different taping of Oprah’s Book Club. And I get it.
Despite what we assume to be an endless supply of shoes in Oprah’s closet, our editors have spotted her wearing the same comfortable ankle boots in multiple colors.
As someone who also wears and loves Vivaia’s footwear, I completely understand Oprah’s dedication to the brand—and why she decided to snag this pair in multiple colors. The brand’s insoles feature ergonomic arch support and plush cushioning for a sneaker-like feel, so you can stay dressed up without any discomfort. In addition to improved arch support and plush feel, this pair also features a diamond pattern stitched into the comfy micro-fibre insole to help relieve pressure on the arch and heel of the foot.
While these particular boots didn’t secure a spot on Oprah’s 2025 Favorite Things List, Vivaia’s warmest pair of boots, the Tyler 2-in-1 Detachable PufferTherm Warm Boots, did get a shout-out. But we wouldn’t be surprised to find the Regina Pros on this year’s list, which have stretchy sock-like uppers for easy on-off that the foot for additional support. Even better, the knit fabric is also water repellent, making it a perfect choice for rainy weather (and even snow!). The square toebox is roomy, and the unique, two-inch block heel is structured for all-day comfort.
Oprah always knows exactly what the people want, which is why we’re not surprised to see these boots have a five-star rating from more than 1,700 reviewers, in addition to her own approval. “Kept my feet dry and comfortable through 6.5 miles of walking in the rain and steep terrain,” one reviewer said. “SO COMFY!” wrote another. “These have literally become my walking shoe.”
A pair of comfortable boots is a closet must-have, and Oprah’s navy Vivaia boots are already out of stock in some sizes, so I recommend acting quickly if you want to score her exact pair. But if it’s already too late to snag a pair in your preferred size or color, fret not. I’ve rounded up a few similar styles to shop on Amazon, below.
Shop More Stylish Ankle Boots on Amazon
VIVAIA Regina Pro Booties
CUSHIONAIRE Russel Knit Ankle Boot
Now 33% Off
VIVAIA Ryan Slip-On Chelsea Boots
DREAM PAIRS Retro Elastic Chelsea Ankle Boots
Now 20% Off
Amazon Essentials Knit Stretch Ankle Boots
Lauren Gruber is an commerce editor at Hearst Magazines, where she writes for publications like Good Housekeeping, Cosmopolitan, Prevention, Country Living, House Beautiful, and more. She has over four years of professional experience covering a variety of lifestyle topics from home to fashion, with an advanced background in beauty and fragrance. When she’s not researching the most worthy Prime Day deals or hands-on testing all the latest perfume launches, Lauren is probably hanging out with her cat Serafina or flexing her AMC A-List membership at the movie theater. You can find her previous work at Entertainment Tonight, Shop TODAY, USA Today, Self Magazine, L’Officiel USA, V Magazine, and Modern Luxury Media.
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