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Just last week, Oprah paid a visit to New York City for the first time since the pandemic, meeting up with King for a visit to see the Broadway revival of August Wilson's play The Piano Lesson at the Ethel Barrymore Theatre.
Throughout her trip, Oprah tapped some cozy styles to stay warm through the harsh East Coast weather, but it was her final look leaving the Four Seasons Hotel New York Downtown that caught our eye. The media mogul layered a luxurious striped wrap over an oversized turtleneck. And because it was rainy, the star wore one of winter's staple boot styles to stay dry: Chelsea boots.
Made of water-resistant material, Chelsea boots are slip-on boots with an elastic side panel that is designed to keep you warm and dry. The rubber sole provides ample traction, so they are a great choice for rain, snow, or sleet — and we found so many stylish and comfortable pairs starting at $29.
Chelsea Boots Inspired by Oprah Winfrey
Soda Pilot Lug Sole Chelsea Boot, $28.95–$59.95 (orig. $108.99); amazon.com
Sorrel Hi-Line Chelsea Boot, $104.95 (orig. $175); zappos.com
Cushionaire Sasha Slip-On Chelsea Boot, $49.99; amazon.com
Toms Charlie Chelsea Boot, $59.96–$83.98 (orig. $119.95); nordstrom.com
Athlefit Lug Sole Chelsea Boot, $53.99 (orig. $65.98); amazon.com
Chinese Laundry Piper Fine Faux Suede Chelsea Boot, $89.95; nordstrom.com
Sam Edelman Laguna Waterproof Boot, $99.37 (orig. $170); zappos.com
The Lug Sole Chelsea Boot by Soda Pilot is beloved by shoppers for its sleek style and level of comfort. Plus, it's Amazon's best-selling Women's Ankle Bootie. The boots have a croc-embossed pull tab that makes slipping them on so effortless, and the elastic side panels offer lots of breathing room for your feet while you walk around. They also feature a durable rubber lug sole block heel that has traction, and as a bonus, you can snag them for up to a whopping 73 percent off right now.
Buy It! Soda Pilot Lug Sole Chelsea Boot, $28.95–$59.95 (orig. $108.99); amazon.com
One of Oprah's favorite shoe brands also makes a popular Chelsea boot (and it's on sale). Designed with a waterproof sealed seam, the Sorel Hi-Line Chelsea Boot is made for rainy days, keeping the wet elements out so you can stay warm and dry. The shoes have a synthetic insole that cushions your feet, plus a molded rubber outsole that's designed to grip the earth while you walk. You can get these sustainable-certified shoes in five staple colors: black, brown, yellow, chestnut, and gray.
Buy It! Sorrel Hi-Line Chelsea Boot, $104.95 (orig. $175); zappos.com
If you want a higher platform without compromising comfort, the Sasha Slip-On Chelsea Boot by Cushionaire are it. Featuring a 2-inch block heel, the shoes can be dressed up if you pair them with baggy jeans, leather pants, or a skirt. The outer is made from vegan leather, so you'll still stay protected from the elements, and they also have a memory foam insole to offer your feet even more support as you walk. "They are super comfortable and my feet don't grow weary after a long day of wearing them," one reviewer said.
Buy It! Cushionaire Sasha Slip-On Chelsea Boot, $49.99; amazon.com
Rain or shine, Chelsea boots are a comfortable and practical way to look stylish and stay dry. Shop more booties from Amazon, Nordstrom, and Zappos below.
Buy It! Toms Charlie Chelsea Boot, $59.96–$83.98 (orig. $119.95); nordstrom.com
Buy It! Athlefit Lug Sole Chelsea Boot, $53.99 (orig. $65.98); amazon.com
Buy It! Chinese Laundry Piper Fine Faux Suede Chelsea Boot, $89.95; nordstrom.com
Buy It! Sam Edelman Laguna Waterproof Boot, $99.37 (orig. $170); zappos.com
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