These Classic Ankle Boots Go With Everything You Own—Chelsea FTW (2024)

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

“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