One of the best things about colder weather is Chelsea boots. They’re streamlined, easy to slip on and off, and have been classic since mods made them cool in 1960s Britain. To find the best Chelsea boots out there, we reached out to stylists and fashion bloggers for their favorites, from sleek black leather ones to tan versions with a high heel. Below, 31 stylish pairs — a mix of their recommendations and ours.
The best classic Chelsea boots
This chunky take on the Chelsea was called out as a favorite by two of our panelists, including London fashion writer Pandora Sykes, who says she’s “currently living in a pair of chunky-soled, patent oxblood short Chelsea boots. I just know that they’re the ideal shoe for a woman with a young baby! Next on my list are a white pair.” Freddie Harrel, Blogger turned founder of ethical hair extensions company Big Hair No Care, also loves the Dr. Martens Chelsea for its thick sole and signature yellow line. “This pair adds an extra badass edge to any outfit,” she says.
Fashion stylist Lindsey Shores also chose Dr. Martens’s Chelsea boots, but in the ’90s-influenced Bianca style, which features a shorter shaft and a triangular elastic side panel. “Style them with frayed jeans, trousers, or a midi skirt for some ‘Avril’ funk,” she says.
Jane Aldridge of the blog Sea of Shoes recommends these Chelsea boots by Daryl K. “I always wear them a lot this time of year,” she says. “They’re about as classic as it gets, and I always get compliments on them when I wear them. Great travel boots, too.”
Celebrity stylist Tara Swennen, who is best known for dressing Kristen Stewart, recommends Frye’s Melissa boot: “This is a staple boot that’s not only durable but also super sleek.”
Brooklyn-based fashion blogger and stylist Allison Graham behind the website She Does Him, which tracks her European-menswear-inspired style, likes these men’s boots by Saint Laurent in a tan suede. “I’ve always been a huge fan of Saint Laurent’s Chelsea boots, as I’m very big on quality and colors.”
For a super comfortable version, try these boots by podiatrist-approved brand Vionic.
“I have had these boots for years, and they are my all-time favorites,” says London-based fashion blogger and stylist Alex Stedman. “They’re such a classic pair, and they’ll definitely come into their own again this season.”
For something luxurious, Mimi Cuttrell, stylist to stars like Gigi Hadid, Priyanka Chopra, and Ariana Grande, loves these Chelsea booties from the Row: “I am a sucker for anything cozy. The cashmere ankle in these Row boots represent just that.”
The best high-heeled Chelsea boots
Swennen recommends this white pair with a pointed toe and elevated with a spiky stiletto that screams mod. “The perfect minimal and effortless-cool-girl boot that your wardrobe has been needing,” she says.
According to fashion and lifestyle blogger Madelynn Furlong of Wide Eyed Legless, the very best Chelsea boots are old Céline, which she says you can find on resale at times, but the closest dupe to that elusive pair’s chunky heel and smooth leather is this style from Church’s.
The best Chelsea-inspired boots
Graham also recommends these Western-inspired boots by Amiri, a line she loves: “I love how different and unique his Chelsea boots are. Another one of my favorites, and per usual, quality truly matters to me.” They are available in both men’s and women’s sizes.
For something a little edgier, Aldridge recommends these chunky Eytys boots that she’s been eyeing for a while: “I love any boots with monstrous proportions, so these clunky Chelsea boots caught my eye immediately. Got to love a steel toe, too; it definitely sets a tone.”
Photographer and graphic designer Shini Park of Park and Cube likes these square-toed socklike boots from By Far: “These ankle boots are the perfect ‘winter whites.’ Pair with classic jeans or with a skirt — great heel height for stomping around, too.”
Park also recommends this avant-garde pair that is “a delicious, edgy twist to the classic Chelsea boots,” she says. “I love the odd leg length, and with the hourglass-heel, it’s almost futuristic! Perfect to pair with a miniskirt.”
The Strategist is designed to surface the most useful, expert recommendations for things to buy across the vast e-commerce landscape. Some of our latest conquests include the best acne treatments, rolling luggage, pillows for side sleepers, natural anxiety remedies, and bath towels. We update links when possible, but note that deals can expire and all prices are subject to change.
Every editorial product is independently selected. If you buy something through our links, New York may earn an affiliate commission.