If we had to pick one shoe from our entire closet to wear season after season with every one of our outfits, it would be the versatile Chelsea boot. The traditional style of the easy pull-on boot, which is usually made with leather and elastic gores and hits under the calf and above the ankle, has become a mainstream, must-have silhouette, according to fashion experts.

“Identified by its clean, utilitarian look, it is arguably one of the hardest working shoes in your closet,” says Kyla Flax, head of styling at Anthropologie, who pairs hers with everything from a long dress and an oversized blazer to the simplest of jeans-and-a-tee outfit. While many designers lean into the clean classic status of the Chelsea, today there are varying styles with updated design details like bright colors, platform lug soles, higher ankle shafts, and new toe shapes. After speaking to style experts and raiding our own closets, we found the best Chelsea boots that are comfortable to wear, durable, and go with all kinds of outfits.

Best Overall

Marc Fisher LTD Yale Chelsea Bootie

What We Love: The shorter heel, lower shaft height, and neutral colorways give the boots a universal look you can take with you everywhere, throughout all four seasons.

What We Don’t Love: The sizing runs small.

Consider the Marc Fisher Yale boots as the foundation of every outfit moving forward. They stop just short of ankle height and flatter any kind of bottom from swing skirts to raw-edged denim. We’re also fond of additional design details like the sharp pointed toe, V-shaped sides, and metal accents, that jazz up the silhouette. No way these will fall by the wayside of your boring everyday footwear — the gorgeous glossy leather and soft suede materials wouldn’t allow for that — but they’re still so endlessly versatile. And, you can send your style soaring by pairing it with a brightly colored bobby or lace-trimmed sock peeking out of the edge. One more note: We’d recommend sizing up for the most comfortable fit.

Size: 5–11 | Colors: 3 | Material: Leather | Heel Height: 1.5 inches

Best Budget

Vepose Chelsea Ankle Booties

What We Love: The non-slip rubber sole makes walking on wet surfaces easy as well. 

What We Don’t Love: The non-leather material can scuff easily.

It’s typically not easy to find Chelsea boots that are affordable because their signature material, leather, is not cheap. Swap it out for something vegan, like this synthetic leather, and you can slash the price down and go animal-free in one go. But don’t worry, the alternative leather is just as comfortable. The heel height is 1.7 inches tall, and the sole follows the foot's natural arch, so walking doesn’t feel awkward. The bottom also features a non-slip rubber making it easy to maneuver over slippery surfaces. Some have noted, however, that because it isn’t really leather, the boot tends to scuff easily, so wear it with care. 

Size: 6–11 | Colors: 6 | Material: Synthetic leather | Heel Height: 1.7 inches

Best Splurge

R13 Single Stack Chelsea Boots Single Stack Chelsea Boots

What We Love: From the worn finish to the exposed back zipper, these boots are loaded with personality.

What We Don’t Love: It could take a few days to break into the leather.

If you’re ready to make the world your stomping ground, you’re ready to wear these awe-striking boots. The soft calfskin leather, which may take a few wears to break in, will only get better with age, and, “the worn-in look gives them a cool, vintage effect,” adds Caroline Maguire, Fashion Director at Shopbop.

Though they may seem effortless, every detail of the boot is meticulously thought through: The edgy back zipper detail makes for easy on-and-off styling and the red contrast stitching offers subtle color pop. Do we need a zipper with thick pull tabs? No. But does it make the boot look that much cooler? Absolutely. Plus, the low-stacked heel makes it easy to wear these in a variety of situations and seasons, and it still adds enough heft to elevate the boot’s silhouette. 

Size: 5–12 | Colors: 1 | Material: Calfskin | Heel Height: 1.5 inch

Best Brown

Aeyde Jack Calf

What We Love: The stunning, glossy leather brown boots boast durable leather and a timeless style. 

What We Don’t Love: There are no half sizes.

Wowing us with a rich chestnut colorway, the beautifully constructed Aeyde Jack Calf could be the one boot we wear every day until the end of time. “These are great because they have a slightly higher shaft,” says stylist and author Laurel Pantin. “If you like wearing ankle crops in winter, these will fit nicely under your trouser legs, and keep your ankles warm.”

Ramping up their versatility, the boots also feature an almost 2-inch heel height, which strikes a happy medium between elevated, fancy footwear you can wear with formal attire or trotting about town. 

Size: EU35–EU42 | Colors: 2 | Material: Leather | Heel Height: 1.8 inches

Best Waterproof

Bernardo Briton Rain Boot

What We Love: Still durable and waterproof, your traditional rain boot just got the most adorable upgrade.

What We Don’t Love: The back bow frequently becomes untied.

We’ve owned this pair of Bernardo Rainboots for over five years and not only are they some of the best waterproof boots we have, but they still look brand spanking new. The classic almond-shaped toe and slim, curved silhouette haven’t fallen out of style, either, and they remain a staple in our outfit rotation even when we’re facing blue skies. “Coming in four different colorways, the dark green boot has a special color pop that I'd wear with a utility pant tucked in,” Flax says.

One minor, frustrating detail is how we find ourselves frequently having to re-knot the back bow, but on the plus side, the straps aren’t so long they’re left dragging if they do become untied.

Size: 6–11 | Colors: 5 | Material: Synthetic leather | Heel Height: 1.25 inches

Most Comfortable

Blundstone Original 500 Chelsea Boot

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. If you live in a wet climate, these could be a stylish rain boot option.

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.

Size: 5–14 | Colors: 7 | Material: Water-resistant leather | Heel Height: Not listed

Best for Winter

Dr. Martens 2967 Smooth Leather Boots

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 pairs 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.

Size: 5–12 | Colors: 1 | Material: Leather upper with rubber sole | Heel Height: 1.5 inches 

Best Leather

Frye Jean Chelsea

What We Love: The durable leather looks great now and develops a gorgeous patina over time.

What We Don’t Love: The heel may be too high for everyday wear.

Offered in four rich, stunning leather and suede colorways and half sizes (a major score for us in-betweeners), we challenge you to find an occasion you can’t wear these stunning leather Chelsea boots. The delicate exposed stitching along the V-shaped elastic sides, the beautifully worn-in leather look, and the almond-shaped toe all lend an elegant Western style that’s anything from kitschy. Although we’re itching to pair some longer flare jeans with the higher block heel and take ‘em, well, everywhere, the height may limit those who prefer their footwear closer to the ground.

Size: 5.5–12 | Colors: 4 | Material: Leather | Heel Height: 2.6 inches

Best Heeled

& Other Stories Heeled Leather Chelsea Boots

What We Love: The block heel makes walking still comfortable.

What We Don’t Love: It doesn’t come in half sizes, and they run large, so finding the perfect fit can be tricky.

Let’s collectively take a moment to appreciate how beautiful these heeled Chelsea boots are. The sleek, smooth leather goes uninterrupted from the toe to the calf, where the boot ends in a square toe. The heel lifts you 2.9 inches off the ground, which may sound like a lot, but due to the block nature of the heel, won’t feel all that uncomfortable. You can easily dress this style up or down. The shoes offered at & Other Stories are never offered in half sizes, and we found that they run quite large, so size down if you’re between sizes! 

Size: 4–11 | Colors: 2 | Material: Leather | Heel Height: 2.9 inches

Best Lug Sole

Hunter Flatform Chelsea Boots

What We Love: We’re confident we could hike Mount Everest in these lug-soled stompers, and with a preppy and put-together look while we’re at it. 

What We Don’t Love: We’d love additional color options.

The Hunter Flatform Chelsea boot marries two types of people: The outdoorsy types who want the added traction and enhanced grip the lug soles provide for everyday wear and tear and the city-slicking folks who want the stylish, extra heft of a heel without any of the discomfort. “I find myself really drawn to the simplicity of the Hunter Flatform Chelsea Boots with the contrasting gum sole,” Flax says.

The knit ribbed elastic inset provides an eye-catching contrast against the durable leather material, and they’ll stretch like a little sweater around ankles for extra comfort. The neutral taupe colorway has a chameleon-like tendency to blend in with whatever you wear it with, which could be a good or bad thing depending on if you’re trying to make a statement. 

Size: 5–11| Colors: 1 | Material: Water-resistant recycled nylon | Heel Height: 1 inch

Best Patent

Inez Pilar Platform Boot

What We Love: The 4-inch heel is delightfully deceptive — we could walk for miles in these sky-high beauties. 

What We Don’t Love: They take a little time to break in (about one good wear).

Would you believe us if we told you that the 4-inch patent leather platform Inez Pilar platform boots are the most comfortable shoes we own? It’s true — between the roomy almond-shaped toe box, supremely soft and stretchy calfskin leather, and cushioned arch support these may as well be orthopedics. And, while the stretch side panels keep the core integrity of a classic Chelsea boot, from there the silhouette has a life of its own, including a 1-inch platform and sleek back zipper to round out the sexy style. Trot around in the boots for one good day to allow the leather to stretch slightly, and they’ll be yours forever.

Size: 6–10.5 | Colors: 2 | Material: Italian calf leather | Heel Height: 4 inches 

Best Suede

Thursday Boots Duchess Chelsea Boot

What We Love: It comes in various suede colors.

What We Don’t Love: The color of the interior rubs onto your sock sometimes.

InStyle writer Bianca Kratky owns a pair of Chelsea boots from Thursday Boots and can confirm just how comfortable they are. Although the ones she owns aren’t suede, she can speak on the interior and general makeup of the shoe, which is that they are sturdy yet soft. The leather molded around her foot to become a custom fit. She has even worn them in the rain with no water seeping through the seams. The short heel is just enough to curve along the natural arch of the foot, keeping it from feeling strained. They’re easy to slip in and out of and don’t scratch around your ankles like some ankle boots do.

Be aware, however, as there have been several occasions when she pulled her foot out of the shoe only to find some of the coloring from the interior rubbed onto the fabric. 

Size: 5–12 | Colors: 18 | Material: Leather and suede | Heel Height: 2 inches

Best for Wide Feet

Schuh Wide Fit Colette Chelsea Boots

What We Love: Wider feet have plenty of breathing room tucked away in these adorable black booties.

What We Don’t Love: Synthetic leather may not be the most durable material.

It can be difficult to find shoes stylish and comfortable enough to accommodate wide feet, a fact that only makes us appreciate this budget-friendly style more. We adore how these boots not only boast a cool-girl, laissez-faire style, but the designer specifically made them with wide feet in mind by providing extra room.

They’ll get you where you need to go, but they’re likely here for a good time, not a long time since synthetic leather doesn’t typically hold up as well. On the flip side, it is an easy material to wipe clean so the boots will always look in tip-top shape. 

Size: 5–10 | Colors: 1 | Material: Synthetic leather | Heel Height: 1.5 inches

Best for Flat Feet

Merrell Women’s Chelsea Boot

What We Love: A lightweight cushioned midsole supports flat arches. 

What We Don’t Love: The fit runs narrow.

Complete with all the bells and whistles of a utilitarian hiking boot, such as a lugged pattern on the outsole for increased traction, odor control footbed, and waterproof leather, the Merrell Women’s Chelsea remains as chic as ever. The round toe gives them a softer, more feminine shape and the creamy snow-white colorway adds an understated elegance to the boot. And, the plush cushioned midsole provides ample support to flat arches so you can schlep around all day in the rain and mud, then wipe the smooth leather clean for dinner and drinks. Though the shoes run a bit narrow, the stretchy, non-stiff leather molds to your feet with wear and ensures a comfortable fit.

Size: 5–11 | Colors: 2 | Material: Leather | Heel Height: Not listed

Best Black

Reformation Katerina Lug Sole Chelsea Boot

What We Love: Good-looking, sustainable footwear is hard to come by, so we’re not letting this gorgeous leather boot out of sight. 

What We Don’t Love: It may not have significant arch support.

If you haven’t heard, sustainable is the new black, or perhaps, it can be both? Featuring rugged pebbled leather and a sporty lug sole, The Reformation Katerina tries to fool us into thinking it's a casual piece of footwear, however, we know better.

Between its elegant, lithe silhouette and supple, easy-to-break leather, it won’t pass by anyone as your everyday, ordinary work boot. Plus, the bovine leather is an easy-to-break-in, long-lasting material, meaning these shoes are here for the long haul. Dress these boots up or down, and your outfit is guaranteed to look elevated no matter what you pair this masterpiece with. 

Size: 5–11 | Colors: 1 | Material: Bovine leather | Heel Height: 1.4 inches

Best for Walking

Margaux Chelsea Boot

What We Love: Its water-resistant material and traction-grabbing sole allow you to trek everywhere and in all weather. 

What We Don’t Love: The style runs a little narrow.

“I’ve walked thousands of steps in these, including through the middle of a New York City snowstorm, and they’ve held up for years — I’ve never slipped in them either,” says InStyle Senior Commerce Editor Zarah Kavarana. The durable suede material is incredibly resistant against whatever dirt and sludge you throw at it, and increased traction on the bottom prevents any tripping. We’d wear your thinnest sock and tights with this pair though, because the style already tends to run narrow. 

Size: 3–14 | Material: Suede | Heel Height: 1 inch | Colors: 2

What to Keep in Mind

• Material: 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? If you foresee yourself braving snow and sleet, consider water-resistant leather. Will you need to treat the material before wearing the shoes 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. 
• Fit: “The Chelsea boot is a tighter fit, originally, it was commissioned by Queen Victoria as an easier riding boot, so it's meant to be easy to pull on, but durable,” says Flax, often goes up a size to best accommodate her wide feet. Pantin agrees, explaining that while you want a snug fit, this everyday shoe should still be roomy enough to accommodate socks.

Your Questions, Answered

How do you wear Chelsea boots?

“Don’t be afraid to play with the types of bottoms you pair with Chelsea boots: Skirts, wide-leg or cropped are all fair game,” says Flax. For example, she suggests pairing a lug-sole, brightly colored Chelsea boot with an overtly feminine dress for something more formal. And, “For colder weather months, I love a sleek sweater set with a clean classic style and one unique detail like a square toe or taller ankle shaft.”

Since this footwear style is typically low, Pantin doesn’t recommend tucking Chelsea boots into jeans. “I would wear them with cropped kick flares though so that they go up under the opening of the pant and cover your ankles,” she says, adding “They're also cute with midi-length, preppy skirts — ideally with a tiny bit of sock poking out of the top.”

Are Chelsea boots good for walking?

Part of what makes Chelsea boots so versatile is that they’re great for work and play because they often incorporate functional and stylish design details like lug soles, cushioned insoles, and durable leather. As Flax explains, “I want these boots to walk many miles, so a flat sole is a fit for me, but I also love the lug soles as they offer a fresh update that I can wear dressed up or down.”

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 crew 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.

Why Shop With Us

Irene Richardson is a fashion and beauty commerce writer for InStyle. She updated this article with additional product picks and valuable insight from Kyla Flax, Head of Styling at Anthropologie; Laurel Pantin, a Los Angeles-based stylist, creative director, and writer; and Caroline Maguire, Fashion Director at Shopbop.

Megan McCarty is a full-time freelance writer who writes about everything from design to beauty to fashion.