Say hello to your new staple shoe
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If I had to guess how many times per week I reach for my best Chelsea boots, I’d say at least five. I can’t help but let my winter outfits revolve around these sleek black shoes. Time and again, they’ve gotten me through every type of occasion—particularly when it’s cold, and getting dressed feels like more of a challenge.
Whether I’m heading out for a casual day of press appointments or meeting up with my girls at our favorite wine bar, I can depend on the best Chelsea boots to take me from one event to the next effortlessly. During the day, you’ll find me wearing my precious shoes with a pair of jeans, a fitted turtleneck, and my go-to trench coat. By night, I’ll transform my look with a satin slip skirt, a chunky knit sweater, and a lengthy wool coat.
Fashion experts agree these boots are more versatile than others. “Chelsea boots are wardrobe building blocks because they’re versatile and timeless,” says Joni Pangsaeng, senior director of design and merchandising at Reformation. Take a moment to look back through fashion history, and you’ll notice that Chelsea boots have proven their tenacity over decades. It all comes down to their inherently uncomplicated design, according to Nordstrom women’s fashion director Rickie De Sole. “It’s an iconic shoe that’s easy to wear thanks to its slip-on-and-off functionality."
Shop the 15 best women’s Chelsea boots that will pull together any look with ease, all winter long, ahead.
One of the best ways to upgrade your collection of statement accessories is to invest in a pair of ivory-colored shoes. Sam Edelman’s Chelsea boots will draw the perfect amount of attention to your outfit without overwhelming your look.
What reviewers are saying: “Love these shoes! They fit true to size and are so comfy, I can wear them all day. They go with everything and are so cute! Definitely recommend!”
“The Katerina is one of my absolute favorites and a style that has been in the collection since we first launched boots,” Pangsaeng says. It’s not surprising these sleek boots have remained a steady part of Reformation’s boot collection. The sensible silhouette and durable construction keep them relevant year after year.
If you’re going to splurge on Chelsea boots, De Sole recommends this pair from Prada, which can easily be dressed up or down. “They look just as good peeking out from the bottom of a romantic skirt as they do accompanying a high-rise straight-leg jean,” the fashion director says.
What reviewers are saying: “Such beautiful boots! Can style in many ways. Pricey but worth it!”
For drizzly days, you’ll want to slip into this pair of Hunter boots, which fuse the functionality of a rain boot and the style of a Chelsea. Their natural latex rubber will keep you completely dry in the strongest showers.
What reviewers are saying: “These are perfect for keeping your feet dry as the weather turns wetter and colder.”
These Tod’s Chelsea boots might be made of supple suede, but that doesn’t mean they’ll lose their sturdy shape over time. Thanks to the leather backing on these boots, they’ll last for years to come.
Not all Chelsea boots are low to the ground. With a three-inch heel, this pair from Tory Burch is a departure from the typical Chelsea design. If you’re concerned about comfort, don’t stress. These shoes are made with a chunky block heel and a cozy leather sole for extra support.
What reviewers are saying: “I’m always on the hunt for a classic comfortable and versatile bootie and these checked all the boxes!”
Manolo is widely known for its high-heeled satin pumps (thank you, Carrie Bradshaw), but the low-heeled shoes are just as fantastic. If you despise the idea of walking around in stilettos, let us introduce you to the designer’s Chelsea boots—your new go-to shoe.
If you peer into my closet, you’ll immediately discover shades of caramel, chestnut, and my personal favorite, chocolate. I’ve always believed that brown fits perfectly into any winter color palette, so good luck trying to convince me I don’t need Gianvito Rossi’s leather boots this season.
Wearing a boot with a heel is the best way to boost your look (literally). For those days when your outfit feels a bit too dull, consider trying on Ganni's Chelsea boots with a 1.5-inch platform.
An oversize buckle adds some glamour to a shoe that otherwise conforms to Chelsea boot standards. There’s absolutely nothing wrong with keeping it simple—trust me, minimalism is the foundation of my wardrobe—but sometimes it doesn’t hurt to spice things up a bit. Gold hardware will always do the trick.
We often think of wearing cashmere in the form of a sweater or scarf, but this soft fabric can also be worn on our feet. Gabriela Hearst’s Hobbes shoes aren’t the first pair of cashmere-trimmed boots I’ve seen, and they certainly won’t be the last. They’re that warm.
Veronica Beard’s Winnie shoe is a fascinating hybrid of two styles. The stretchy elastic side panels reference the classic features of a Chelsea boot, while the thick rubber sole speaks more to the iconic design of a combat boot.
As if fitting into a pair of Chelsea boots couldn’t get any easier, the Row introduced an innovative design that features a front zip fastening. If you’re bundling up with a pair of heavy socks, slipping into these shoes is not a problem—just ask the dozens of fashion insiders who wear them all winter.
If your foot is on the wider end of the spectrum, you’ll want to look for a Chelsea boot crafted with elasticized gussets, such as this pair from Proenza Schouler. This feature increases the shoe’s flexibility, specifically around the ankle area, to provide a seamless slip-on-and-off experience.
Subtle styles resonate more with me, but I’ve found ways to experiment with embellished looks. I love the way Valentino’s signature gold hardware shimmers against the polished leather backdrop of these Chelsea boots.
For more than 150 years, Harper’s Bazaar has been the preeminent fashion, beauty, and lifestyle resource for women at every age. We cover what’s new and what’s next in fashion by working with the world’s leading authorities in ready-to-wear, footwear, accessories, and more. Every story we publish has been thoroughly researched and vetted by our team of editors and industry experts.
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