Best Designer Chelsea Boots
Prada Chelsea Boot
Best Designer Chelsea Boots
Prada Chelsea Boot
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!”
Sizes: 5–10
Colors: Black
Materials: Leather, rubber
Best Waterproof Chelsea Boots
Hunter Original Waterproof Chelsea Rain Boot
Best Waterproof Chelsea Boots
Hunter Original Waterproof Chelsea Rain Boot
Now 45% Off
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.”
Sizes: 5–11
Colors: Red, green, black
Materials: Rubber
Best Everyday Chelsea Boots
Reformation Katerina Lug-Sole Chelsea Boot
Best Everyday Chelsea Boots
Reformation Katerina Lug-Sole Chelsea Boot
“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.
Sizes: 5–11
Colors: Black
Materials: Leather
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Best Suede Chelsea Boots
Tod’s Suede Chelsea Boots
Best Suede Chelsea Boots
Tod’s Suede Chelsea Boots
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.
Sizes: 34–42 IT
Colors: Black, brown
Materials: Suede, leather
Best Ivory Chelsea Boots
Sam Edelman Laguna Waterproof Lug-Sole Chelsea Boot
Best Ivory Chelsea Boots
Sam Edelman Laguna Waterproof Lug-Sole Chelsea Boot
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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!”
Sizes: 5–12
Colors: Ivory, black, brown
Materials: Leather
Best High-Heeled Chelsea Boots
Tory Burch Banana Chelsea Boot
Best High-Heeled Chelsea Boots
Tory Burch Banana Chelsea Boot
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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!”
Sizes: 5–11
Colors: Black, brown, multicolored
Materials: Leather, textile, rubber
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Best Brown Chelsea Boots
Gianvito Rossi Leather Chelsea Boots
Best Brown Chelsea Boots
Gianvito Rossi Leather Chelsea Boots
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.
Sizes: 36–41 IT
Colors: Brown
Materials: Leather
Best Buckled Chelsea Boots
Roger Vivier Viv Rangers Buckled Leather Chelsea Boots
Best Buckled Chelsea Boots
Roger Vivier Viv Rangers Buckled Leather Chelsea Boots
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.
Sizes: 35–42 IT
Colors: Black
Materials: Leather
Best Low-Heeled Chelsea Boots
Manolo Blahnik Chelata 30 Leather Chelsea Boots
Best Low-Heeled Chelsea Boots
Manolo Blahnik Chelata 30 Leather Chelsea Boots
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.
Sizes: 34–43 IT
Colors: Black
Materials: Leather
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Best Cashmere-Trimmed Chelsea Boots
Gabriela Hearst Hobbes Ribbed Cashmere-Trimmed Leather Chelsea Boots
Best Cashmere-Trimmed Chelsea Boots
Gabriela Hearst Hobbes Ribbed Cashmere-Trimmed Leather Chelsea Boots
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.
Sizes: 36–42 IT
Colors: Beige, black
Materials: Leather, cashmere
Best Platform Chelsea Boots
Ganni Patent-Leather Platform Chelsea Boots
Best Platform Chelsea Boots
Ganni Patent-Leather Platform Chelsea Boots
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.
Sizes: 35–41 IT
Colors: Black
Materials: Leather, rubber
Best Chelsea Boots With a Zip Fastening
The Row Beige Zipped Boots
Best Chelsea Boots With a Zip Fastening
The Row Beige Zipped Boots
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.
Sizes: 35–42 IT
Colors: Beige
Materials: Leather, rubber
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Best Embellished Chelsea Boots
Valentino Garavani Vlogo Embellished Leather Chelsea Boots
Best Embellished Chelsea Boots
Valentino Garavani Vlogo Embellished Leather Chelsea Boots
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.
Sizes: 35–41.5 IT
Colors: Black
Materials: Leather
Best Chelsea Boots With Elasticized Sides
Proenza Schouler Beige Lug-Sole Boots
Best Chelsea Boots With Elasticized Sides
Proenza Schouler Beige Lug-Sole Boots
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.
Sizes: 35–41.5 IT
Colors: Beige/ black
Materials: Suede, rubber
Best Hybrid Chelsea Boots
Veronica Beard Winnie Water-Resistant Leather Lug-Sole Chelsea Booties
Best Hybrid Chelsea Boots
Veronica Beard Winnie Water-Resistant Leather Lug-Sole Chelsea Booties
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.
Sizes: 4–12
Colors: Black
Materials: Leather, rubber
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