The 10 Best Chelsea Boots for Women To Wear for Years to Come

You’ll want to add Madewell’s Bradley Boot to your online cart immediately

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chelsea boots

Jhett Thompson

Think of the Chelsea boot as the versatility queen in your entire shoe closet. Not only do they slip on and off easily, thanks to the elastic gore on each side of the ankle, but their classic style is sure to elevate any outfit, from a long dress with an oversized blazer to the simplest of jeans-and-a-tee outfit. We’re appreciative of the classic Blundstones of the bunch, but it seems like nearly everyone out there makes their own iteration now, so it can be tough to determine which are better than others. 

That’s why we shopped for you. From suede to leather to heeled to waterproof, we got you — and your growing shoe collection — covered. At the top of our list is Madewell’s Bradley Chelsea Lug Sole Boot, which balances all the traditional features of a Chelsea boot with a few twists that will have you daydreaming about them until they arrive on your doorstep. But keep reading for more of our favorites. 

Best Overall

Madewell Bradley Chelsea Lugsole Boot

Madewell The Bradley Chelsea Lugsole Boot


What We Love: These Chelsea boots are love-them-forever classics, with smart features that make them all-the-more wearable. 

What We Don’t Love: The tall shaft can cuff off in an awkward part of your calf if you’re on the shorter side.

Consider this pair of boots from Madewell the Goldilocks of Chelsea boots. They’re not too clunky, a risk with lug sole boots, nor too expensive either, landing right in the middle of the sweet spot budget-wise, as far as quality boots are concerned. They’ll fit just right, too, since they’re made in half sizes to hug your foot perfectly, no matter its size. 

Madewell’s signature cloudlift lite padding makes walking in these all day a breeze too — which you will, since the wide elastic gore allows for easy taking on and off, even if the slightly taller shaft makes it a bit more challenging. Plus, The goes-with-everything design means you’ll be reaching for these day after day. Now comes the hard part: deciding between the black color or the stable one. (We can’t help you there.)

Price at time of publish: $198

Size: 5 - 12, including half sizes | Material: Leather upper, rubber sole | Heel Height: Not listed

Best Budget

Universal Thread Celina Water Repellant Chelsea Boots

Universal Thread Celina Water Repellant Chelsea Boots


What We Love: These boots boast a classic Chelsea silhouette with an easy-on-the-budget price point. 

What We Don’t Love: They’re not made out of real leather. 

Leave it to Target to prove you don’t have to throw down half your paycheck to add a pair of Chelsea boots to your shoe collection. These are traditional in every way, from the pull tabs to the stretchy elastic sides to the neutral tones. The just-tall-enough heel will give you the optimal amount of lift too, whether you’re tromping through fallen leaves or a dusting of snow.  

While these boots are not made out of true leather, their material is water-repellent, ensuring your feet stay warm and dry on drizzly fall days. The memory foam insoles make for easy all-day wear, while the simple silhouette ensures you can wear them with jeans, a skirt, leggings—you name it—and are guaranteed to look put together.  

Price at time of publish: $40

Size: 6 - 11, including half sizes | Material: Polyurethane, polyester | Heel Height: 1.75”

Best Splurge

Loeffler Randall Raquel Leather Chelsea Ankle Booties

Loeffler Randall Raquel Leather Chelsea Ankle Booties

Saks Fifth Avenue

What We Love: Pairing unmatched quality with comfort makes for the ideal Chelsea boots. 

What We Don’t Love: The price makes you think twice before adding these to your cart.

Morgan Hutchinson, founder and designer of BURU, raves about these crepe-soled Loeffler Randall Chelsea boots with pull tabs in both the front and back. “While I think the simple shape paired with a comfy, rubber heel is already a home run, it's the buttery color that really wows me,” she says. Tan not your favorite hue? They’re also available in cognac and black. 

What she loves most, though, is something you can’t see: they’re seriously comfortable. “Loeffler Randall is known for helping keep our feet feeling good,” she says. “These rubber-soled boots are no exception.” While she often pairs Chelsea boots with a semi-cropped wide leg denim, Hutchinson has another outfit idea for these boots in particular. “I think pairing tonal colors with non-traditional colors — AKA not blue — with a crisp white button-down shirt and an oversized statement coat would be a fun fall combo,” she says.

Price at time of publish: $395

Size: 5 - 12, including half sizes | Material: Leather upper and crepe rubber sole | Heel Height: .8”

Best Leather

Everlane Italian Leather Chelsea Boot

Everlane The Italian Leather Chelsea Boot


What We Love: With these Everlane boots, you’ll get the highest-quality leather without the highest price tag. 

What We Don’t Love: The elastic gore is thinner than other boots on this list, making them slightly more prone to stretching out.

Did your face turn into the heart eyes emoji when you first saw these Chelsea boots from Everlane? Ours did too. If you’re on the hunt for leather boots that won’t blow your budget, this is the pair. The luscious leather upper sourced from Florence, Italy, is silver-rated nappa, meaning it’s soft-to-the-touch and comfortable right out of the box — no blister-inducing break-in period necessary. (The cushioned insole helps too.) Because the gore is a bit thinner than the others on this list, you might notice they loosen with time. Regardless, chances are you’ll still fall in love with them and will  want to add one of each color — black, tobacco, and off-white — to your shoe rack. 

Price at time of publish: $195

Size: 5 - 11, including half sizes | Material: Italian leather | Heel Height: 1.3”

Best Waterproof

Blundstone Women's BL500 Original 500 Chelsea Boot

Blundstone Women's Originals Chelsea Boots


What We Love: The water-resistant leather will keep your feet warm and dry no matter what wacky weather Old Man Winter brings your way. 

What We Don’t Love: The front pull tab, while utilitarian, can feel floppy.

Blundstone means business when it comes to the design of these Chelsea boots. (And, really, all of their shoes.) They’re built to last no matter what you or Mother Nature put them through, from a walk through the woods to drudging through puddles. They feature double stitching, serious shock absorption (as in, the boots will absorb 90 percent of the impact of each step you take), thick water-resistant leather, and a tough outsole that can be put through the wringer. All of those features ensure they’ll still look great at the end of the day — day after day, since you’ll be wearing these for years to come, especially since the leather will mold to your feet over time. The front tab is definitely an acquired taste (some people dislike how it flops over), but it makes pulling on your boots so much easier.

Price at time of publish: $210

Size: 5 - 11, including half sizes | Material: Water-resistant leather | Heel Height: Not listed

Best Heeled

Sam Edelman Rollins Block Heel Chelsea Boot

Sam Edelman Rollins Block Heel Chelsea Boot


What We Love: The thick block heel provides both height and stability.

What We Don’t Love: The tall shaft may be too tall if you have wide calves. 

No wobbly ankles allowed in these high-heeled Chelsea boots. Even though the heel on these boots stands over three inches tall, the stacked block heel design gives you plenty of stability — a must for walking on wet leaves and snow-dusted sidewalks. The extra tall shaft keeps your ankle secure and the cold air out, but for anyone with wide calves, they might feel a bit snug, since they go up higher than your typical ankle boot. 

Price at time of publish: $200

Size: 5 - 11, including half sizes | Material: Leather or suede upper | Heel Height: 3.25”

Best Lug Sole

GANNI Black Cleated Mid Chelsea Boots

Conscious GANNI elasticated ankle ridged-sole boots


What We Love: A lug sole that’s lightweight? Consider us sold. 

What We Don’t Love: That price tag makes buying these a serious decision.

Lug soles can be a bit too extreme sometimes. But not these Ganni boots, which Eloise Reeves, co-owner of Thirty-One Jane, a womenswear boutique in Charlotte, North Carolina, names as her favorite Chelsea boots. The lightweight rubber gives the look of a lug sole without the achy ankles that are often a consequence of heavy soles. “I like that the cleated bottoms give the boot a utilitarian feel, while the white stitching and clear rubber along the sole of the foot provide a level of sophistication and tailoring,” Reeves says. 

The sole isn’t the only feature that qualifies these boots as worth the buy though. “The contrast stitching and clear rubber along the sole makes this boot special — it’s unlike any Chelsea boot I’ve seen before,” Reeves says. “The chunky cleat of the boot adds a true-to-brand Ganni edge to the typical sleek Chelsea boot style.” 

If you’re this close to adding these to your online cart, Reeves has an insider’s tip: size up. “Especially if you want to wear a thicker sock underneath,” she says. “You want to give yourself a little bit more room to work with.”

Price at time of publish: $260

Size: 36 - 41 | Material: Calf leather with extra light thermoplastic rubber sole | Heel Height: 2 inches

Best for Winter

Dr. Martens 2976 Smooth Leather Chelsea Boots

Dr. Martens 2976 Smooth Leather Chelsea Boots

Dr. Martens

What We Love: You can wear these forever-in-style boots through the worst of winter and they’ll still look good in spring. 

What We Don’t Love: This pair is sold in full sizes only.

There’s a reason these Dr. Martens Chelsea boots have been in production since the ‘70s. (If only our mothers kept their pair from that era, we wouldn’t be shopping for new ones.) They’re worth the buy though because they magically defy the decades and the trends that come and go within them. 

If winter hits particularly hard where you live, you’ll not only want these boots, but need them too. The notoriously tough leather will keep your feet dry and warm snowstorm after snowstorm. Then come springtime, give them a good polish to wash off the road salt. While they’ll feel stiff to start, trust the breaking-in process and know they’ll mold to your feet in no time. They don’t come in half sizes, though, so if you’re between sizes, make sure to size up.

Price at time of publish: $170

Size: 5 - 12 | Material: Leather upper with rubber sole | Heel Height: 1.25 inch heel

Best Patent

Greats Hewes Chelsea Boot

Greats Hewes Chelsea


What We Love: These boots feature the luxurious high-gloss of patent leather without feeling too flashy.

What We Don’t Love: They don’t go above a size 10.

Patent leather can be a divisive look. What’s too glossy for some may never be glossy enough for others. That’s why we love the middle-of-the-road shininess of these Greats Chelsea boots, which are made with luxe leather that’s been specially polished with an eye-catching shiny finish and other Earth-friendly materials, like recycled cotton threads and plastic and an EVA footbed. We also appreciate the brand took the extra step (pun definitely intended) in making sure this boot will be as comfortable as possible by giving the foodbed an antimicrobial coating and additional cushioning. The lug sole adds a modern twist to them, too, but they still look classic enough to last you for numerous seasons. Our only qualm: they don’t go above a size 10.

Price at time of publish: $199

Size: 6-10 | Material: Leather, EVA, recycled materials | Heel Height: Not listed

Best Suede

Margaux Chelsea Boot

margaux Chelsea Boot


What We Love: Suede has a reputation of getting ruined in the rain, but these Chelsea boots are weather-resistant.  

What We Don’t Love: If you have wide feet, beware: these are on the narrow side. 

“Water-resistant suede” may sound like an oxymoron, but that’s exactly what these Chelsea boots from Margaux are. Made out of durable German suede that won’t get ruined by a single rainstorm, these boots will look just as buttery soft regardless of the weather you wear them in. Plus, the rubber lug sole ensures you’ll have plenty of traction when walking on slippery sidewalks, too, so you’ll even want to wear them in the rain. 

These boots are intended to be worn with lightweight socks, so if you prefer chunky wool ones to keep your toes warm no matter how far below zero the temperatures dip, opt for a half-size larger because they do run a bit narrow.

Price at time of publish: $345

Size: 33 - 45, with half sizes | Material: Water-resistant suede upper, leather lining, and rubber sole | Heel Height: 1 inch

What to Keep in Mind


Don’t click “add to cart” on any pair of Chelsea boots before taking a good gander at the material makeup. Leather is a classic, and so is suede, but whatever you choose you’ll likely want it to be weather-resistant. A few questions to ask yourself: Is real leather a must, or is faux okay? What type of less-than-ideal weather will you be wearing these in? Will you need to treat the material before wearing or at the end of the winter? No matter what you pick, you’ll want something that lasts a long time.

Heel Height

There’s no right or wrong heel height for Chelsea boots; it’s all personal preference. As you’re shopping, keep an eye on how tall the heel is to determine if it’s a good fit for your wardrobe and lifestyle. Don’t let a little lift scare you away. While something like the Sam Edelman Rollins Block Heel Chelsea Boot might seem intimidating, thanks to wide block heels and cushy soles, a little heel, anywhere from one to three inches or higher, can be (almost) as comfortable as your favorite slippers. 

Your Questions, Answered

What are the best socks to wear with Chelsea boots?

The design, height, and thickness of the socks you should wear with a Chelsea boot depend on the look and warmth level you’re going with. To show off a hint of leg between your boots and the bottom of your pant leg, opt for ankle socks — ones that stay in place, won’t get annoyingly caught under your heel, and can’t be seen.

We’re big fans of a visible sock though. (Warm ankles too.) To achieve that look, opt for a taller sock that just sits an inch or two taller than the shaft of your boot. Keep in mind that if you prefer to wear thick socks with Chelsea boots, you may need to size up to accommodate the extra thickness. “My go-to socks to wear with Chelsea boots are from Bombas, like these Marl Calf Socks, that come in fun colors and are super comfortable,” says Reeves. “Not to mention, for every sock purchased, Bombas donates a pair to charity.”

What is the difference between a Chelsea boot and an ankle boot?

While a Chelsea boot can hit at the ankle, there’s one main feature that differentiates a Chelsea boot from every other style of boot: an elastic gore on either side of the ankle, making for easy taking on and off, no zipper or yanking necessary. Also, Reeves says, “Chelsea boots sit a bit higher on the leg (either above the ankle or higher) and are typically composed of some type of leather with the classic pull tabs in the front and back.”

Why Shop With Us

Megan McCarty is a full-time freelance writer who writes about everything from design, to beauty to fashion. She regularly contributes to outlets like Domino, InStyle, People, Architectural Digest, Bustle, and many more. Aside from using her own expertise and completing lots of research, she interviewed style experts, like Eloise Reeves, co-owner of Thirty-One Jane and Morgan Hutchinson, founder and designer of BURU, for what they think is a worthy buy, too.

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