33 Chic Chelsea Boot Varieties Worth Shopping Right Now
Try as you might, you probably can’t resist the appeal of Chelsea boots. Because while some items suffer from omnipresence—becoming frustrating, repetitive and tedious—Chelsea boots seem to benefit from it. They seem to grow more sleek, more versatile, more necessary with every appearance. No matter how many times they appear in Instagram ads, or on the feet of street style stars, or in the windows of brick-and-mortar stores, they never seem basic. No, Chelsea boots only grow increasingly essential.
When Chelsea boots first pervaded the style sphere a couple years ago, I resisted them. Ankle boots—flat ankle boots—seemed like a strange choice for any season. Too heavy for spring/summer, too ankle-bearing for fall/winter, ankle boots seemed like an impractical choice compared to, say, a pair of killer over-the-knee boots or something similar.
But the more I saw Chelsea boots, the more convinced of their value I became. Short boots suddenly seemed more convenient and more practical than taller options. The ankle-bearing thing started looking less weird—plus, socks could account for the disparity in colder temperatures. By the end of 2017, I’d caved and bought a pair of Chelseas. And when I’d thoroughly worn those out, I bought another. Chelsea boots had officially become a necessity in my wardrobe—carrying me through a number of occasions, both casual and formal, and every season, too. I’d finally taken a sip of the sartorial Kool-Aid, and I was hooked.
These days, Chelsea boots are perhaps more available—and more diverse—than ever before. The Chelsea boot selection is vast and varied, and I’d be lying if I said I wasn’t tempted to shop the whole damn thing. Did you know high-heeled Chelsea boots are on offer now? Snakeskin ones? Metallic gold ones? Dream up your ideal Chelsea boot, and it probably exists. And the best part is: Since winter’s nearing a close, that dream shoe of yours is probably on sale, too.
Marc Ellis Chelsea Boots, $131 at Farfetch
The sock boot trend got a structured makeover, thanks to the Chelsea style. Needless to say, here for this.
A-GAME Chelsea Boots, $108 at Topshop
Who knew utility boots could look this good rendered in a futuristic, metallic shade?
Oasis Heeled Chelsea Boots, $36 at ASOS
In case the cowboy boot trend intrigued you, but not enough for you to sacrifice your go-to Chelseas.
Wide-Fit Bravo Patent Chelsea Ankle Boots, $38 at ASOS
Wide-fit, shiny AF Chelseas—need I say more?
Aeyde Ankle Chelsea Boots, $318 at Farfetch
You know you’d benefit from owning Chelseas in a couple different colors.
Ascend Studded Chelsea Boots, $35.50 at ASOS
Officially party-appropriate (not that OG Chelseas weren’t, of course).
New Look Wide-Fit Chelsea Block Heel Boots, $45 at ASOS
Yup, you can now own leopard print, high-heeled Chelsea boots. Your maximalist prayers have been answered.
Atom Leather Chelsea Boots, $40 at ASOS
Retro and versatile? We’ll take 12.
Alversa Chunky Chelsea Boots, $56 at ASOS
You now never have to take your Chelsea boots off. Not even when you’re hiking.
Evita Conker Leather Chelsea Boots, $41 at ASOS
Perhaps the most office-appropriate take on the Chelsea boots trend.
Alexa Chung Python-Print Leather Chelsea Boots, $150 at Matches Fashion
Snakeskin is pervading everything this year—you didn’t expect it to stay away from Chelsea boots, did you?
Aldo Chelsea Wellie Boots, $33.50 at ASOS
Waterproof Chelsea boots. Need I say more?
Coach Studded Chelsea Boots, $295 at Farfetch
A particularly contemporary spin on the trend.
Hillier Bartley x Crockett & Jones Bonnie Leather Chelsea Boots, $456 at Matches Fashion
Perfect for pairing with your favorite sundress.
Leather Chelsea Boots, $155 at & Other Stories
These are so cute and so comfortable. (Trust me—I used to own a snakeskin pair.)
Fendi Sock Detail Chelsea Boots, $788 at Farfetch
Everything about these sock Chelsea boots screams 2019. (And to be clear, I love it.)
Chalayan Chelsea Boots, $399 at Farfetch
The purple-and-white combo is one I didn’t see coming—but I’m into it.
HOGL Panelled Chelsea Boots, $152 at Farfetch
Maybe the sleekest Chelsea boots on the block.
Alexa Chung Stud Embellished Patent Leather Chelsea Boots, $228 at Matches Fashion
Kind of retro. Kind of edgy. Very fashion-forward.
Moncler Chelsea Boots, $735 at Farfetch
These look super intense, but also super wonderful?
Via Roma 15 Fringed Stud Trim Chelsea Boots, $145 at Farfetch
The fringe trim on the front of these is downright adorable.
ALDO Eraylia Stud Chelsea Leather Boots, $93 at ASOS
Stud-lined Chelsea boots are officially happening.
Stradivarius Elastic Side Chelsea Boots, $64 at ASOS
These look like space boots. And I’m pretty sure they’d pair well with any party piece in your closet.
Marc Ellis Studded Chelsea Boots, $188 at Farfetch
Because the cutout doesn’t have to feature a rounded rectangle.
Harrison High Heel Leopard Ankle Boots, $150 at Topshop
Somehow very 2019 and very 1980 at the same damn time?
Sam Edelman Chelsea Ankle Boots, $177 at Farfetch
Chelsea boots rendered in kitten heel form? A thing I never knew I needed—but am now pretty sure I can’t live without.
Alexander McQueen Black and Red Chelsea Leather Boots, $689 at Farfetch
A pop of red is always a good idea—trust Alexander McQueen on this one.
Our mission at STYLECASTER is to bring style to the people, and we only feature products we think you’ll love as much as we do. Please note that if you purchase something by clicking on a link within this story, we may receive a small commission of the sale.
