These boots were made for walking.
Chelsea boots are wildly popular for good reason. The simple ankle height style is versatile enough to dress up or down, plus they’ve got elastic panels to make slipping in and out of them a walk in the park. Although they were invented during the Victorian era, Chelsea boots got their British nickname after exploding onto the London rock ‘n roll scene during the fifties. (The Beatles were huge fans.)
And they’ve stood the test of time. Today, tons of designers put their twist on the iconic boot — from J.Crew to Doc Martens to Coach. You can find waterproof, printed, heeled, and colored versions. The best part? Most styles come with lug rubber soles, so they’ll hold up against the pavement as you get your steps in. And even though Chelsea boots are trending this season, the style is so functional that they’ll remain a fashion staple for years to come.
Whether your style is classic, edgy, or you like to take chances on trending colors, there’s a Chelsea boot that’s begging to be worn. Not sure how to rock ’em? Toss them on with your favorite jeans and hoodie for an off-duty look, or pair them with a maxi dress and beloved leather jacket for an edgy (but comfy!) night out.
From rubber rain boots to a pair under $50, we rounded up our favorite Chelsea Boots across different categories for you to shop below. So, what are you waiting for? Give your feet the gift of comfort!
Best Classic Chelsea Boot
Ugg Markstrom Chelsea Boot
Zappos
The perfect Chelsea boot does exist. UGG’s slip-on style is crafted with a hard-working rubber sole and genuine leather. It’s the easiest style to rock every day, no matter the occasion.
Best Modern Chelsea Boot
Nisolo Everyday Chelsea Boot
Nisolo
Just as the name implies, this boot is one you’ll want to wear every single day. It has the same timeless silhouette as most Chelsea boots, but the ankle elastic is in a chic “v” shape instead of the “u” shape found on other styles. Pull tabs at the heels ensure you can slip them on easily, and a heavy-duty (but not bulky) sole ensures you don’t slip on slick surfaces.
Best Heeled Chelsea Boot
Hutch Boot by Steve Madden
Steve Madden
If you like your boots to add a little lift to your look, choose this chunky (chic) style by Steve Madden. The elastic at the ankles has a thick ribbed texture, which gives a little extra oomph, too.
Best Chelsea Rain Boot
Sherpa-Lined Chelsea Rain Boots by J.Crew
J. Crew
Slip into these sherpa-lined Chelsea boots from J.Crew on wet days. We also love this sleek and shiny pair by Marc Fisher that has a patent leather look.
Best Trendy Chelsea Boot
Laguna Chelsea Boot by Sam Edelman
Nordstrom
If you already own a pair of black Chelsea boots, then try the trend out with this stone-colored Sam Edelman style. They’re still neutral enough to pair with all of your favorite outfits.
Best Printed Chelsea Boot
Aersoles Camila Lug Sole Boot
Aerosoles
As far as we’re concerned, leopard print is a neutral. Kick up your feet in Aerosoles’ ultra comfy calf hair boots that feature plush padding and a hardworking lug sole.
Best Chelsea Boot Under $50
Dream Pairs Chelsea Ankle Booties
Amazon
Classic Chelsea boots for less than $50? We’ll take two! Just kidding — but this style is so easy to slip on and will become your go-to on fall days spent walking around town.
Best Platform Chelsea Boot
2976 Quad Platform Chelsea Boot by Dr. Martens
Nordstrom
Doc Marten’s makes iconic lug sole boots, and this Chelsea style is sure to standout (and hold up) over the years.
Best Waterproof Leather Chelsea Boot
Caslon Miller Water Resistant Chelsea Boots
Nordstrom
If you want to wear your Chelsea boots throughout the slush of winter, these Caslon boots (made with waterproof leather) are a must-have.
Best Neutral Chelsea Booties
Timberland Courmayeur Valley Chelsea Boot
DSW
Fall in love with these Timberland booties that feature cushion padding and a rubber sole. They also come in three other colors, including that yellow-tan work boot color that Timberland is known for (which is on sale for $60!).
