Photo: Courtesy of the retailer
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.
Dr. Martens Chelsea Boot
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.
Dr. Martens Bianca Chelsea Boot
at Urban Outfitters
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.
Daryl K Chelsea Girl Boot
at Daryl K
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.”
Frye Melissa Chelsea
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.”
Everlane Modern Chelsea Boot
Everlane’s Chelsea boot is classic all the way, too, with a leather heel tab, squared elastic panels, and a toe that’s pointed just so.
Cole Haan Ferri Bootie
These Cole Haans have a shorter shaft — great for cropped trousers.
Saint Laurent Wyatt Men’s Chelsea Boot
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.”
Steve Madden Dover Chelsea Bootie
For something a little more affordable, we recommend these Steve Madden booties in a cognac suede.
Russell and Bromley Cadogan Brogue Chelsea Boot
at Russel and Bromley
“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.”
Tod’s Classic Chelsea Boot
These Tod’s also feature a sophisticated but understated brogue details.
The Row Fara Ribbed Cashmere-Paneled Leather Chelsea Boots
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.”
Blundstone Dress Boots
These Blundstones dress boots, a sleeker take on the original Blundstone work boots, is a similar alternative, even if there’s no cashmere sock to speak of.
Manolo Blahnik Dildi Leather Booties
at Saks Fifth Avenue
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.
Diane Von Furstenberg Mollo Chelsea Bootie
Or try these black booties by Diane von Furstenberg that are a tad less money than the Manolos.
Mason Chelsea Boots
“For another upcoming trend staple, go for a Western-inspired look from Topshop,” says Shore. The chunky heel, pointed toe, and crocodile-effect leather make this pair look tough and glam.
Morty Chelsea Boot
A more streamlined choice from Topshop, this time with angled heel.
Church’s Chunky Heel Chelsea Boots
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.
Jeffrey Campbell Hurricane Waterproof Boot
Here’s a similar style by Jeffrey Campbell that’s waterproof and could theoretically hold up to an inch or two of flooding, thanks to its chunky heel.
For a look with a pointier toe, try these Aldos that also come in patent and suede options.
Everlane Heel Boot
Another elevated style from Everlane. Try the warm cognac color to get you in the mood for fall.
Italian Shoemakers Bonnie
Go a little darker with chocolate leather Chelseas with a 1.5-inch heel.
Amiri Bandana-Strap Suede Jodhpur Boots
at Barneys New York
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.
Eytys Nikita Crocodile-Effect Leather Chelsea Boots
at Matches Fashion
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.”
Dirty Laundry Lisbon Sedona
If you like the chunky block heels and soles of the Eytys boots, try this vegan leather pair for a similar effect.
Calvin Klein Claire Ankle Boots
If Furlong were to buy another pair, she would opt for these (also) Western-inspired Calvin Klein boots: “They have an amazing shape, a sturdiness to them, and I love the metal toe detail.”
Marc Fisher LTD Yale
These Marc Fishers sport a similar vibe with their subtle hardware detailing at the toe. Go with the snakeskin-effect leather to make an even bolder statement.
By Far Estes Leather Ankle Boots
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.”
Calvin Klein Perron
Or go the chunky route with these on-sale, white Calvin Kleins.
Marques’Almeida Hourglass-Heel Leather Chelsea Boots
at Matches Fashion
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.”
Prada Leather and Neoprene Ankle Boots
These Chelsea-inspired ankle boots by Prada feature a neoprene cuff and removable buckles. “I love the combination of neoprene and leather,” says Cuttrell. “The sharp, pointed toe looks great under a sharp pair of mom jeans.”
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