Chelsea boots are the ideal shoe style for transitional weather.
The shoe, named after the posh neighborhood in London, originated in the early 1800s but shot to fame when popularized by The Beatles in the late ’50s and ’60s. The style has since evolved to include boots with chunky soles, tall heels and shafts, and some Western details, while keeping the traditional elements like stretchy gore side panels alive.
Getting a feel of the market before you buy your own pair is necessary, suggests celebrity wardrobe specialist Denise Styless — luckily, we did that work for you. We scoured the internet for the best Chelsea boots, comparing different styles, functions, and price points, then spent over 237 hours testing our top picks to find the ones worth splurging on.
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After comparing 11 styles of Chelsea boots, we were most impressed by the Blundstone Classic Chelsea Boot for its quality, comfort, and overall wear. The shoes are made with water-resistant leather and have a stretchy yet structural elastic detail and durable TPU outsole. They were a bit snug at first (and run a tad small in general), but within a couple of wears, they molded to our tester’s feet well.
In addition to their style, fit, and quality, the boots also have excellent support, especially if you have high arches and need something with a little extra cushion and shape. During the testing period, our tester walked several miles at a time in the boots without experiencing any aches and pains. They’re also versatile (and durable) enough to wear for outdoor activities like hiking as well as more casual occasions like a day at the office.
Sizes: 6–11 | Materials: Water-resistant leather, TPU, elastic | Colors: 8
Editors Say
PEOPLE shopping writer Cai Cramer has owned these boots for over two years. “I wear them constantly: running errands, going out to dinner, and even on short hikes. I probably have worn these Chelsea boots upwards of 300 times — they’re seriously my most worn shoes.”
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Excellent size range
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Roomy toe box
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Easy to pull on and off
These Dr. Martens have a timeless Chelsea boot silhouette with elastic gore, buffed leather uppers, and a durable rubber sole with good traction. When wearing these boots, our tester was impressed by the roomy toe box and the ease of pulling them on and off, thanks to the heel tab. They also have one of the more expansive size ranges on our list.
As much as we love these boots, it’s worth noting that they lack cushioning, so if you need some extra support, consider adding an insole to cushion the soles. And, while it does take a few weeks to break them in (which caused some rubbing against the back of our tester’s lower leg), once broken in, they’re so comfortable.
Sizes: 5–15 | Materials: PVC, rubber, leather, elastic | Colors: 1
Experts Say
The boots are also super versatile and go with everything you own, says celebrity wardrobe stylist Pilar Scratch. “These are edgy yet sophisticated,” Scratch tells PEOPLE. “You can style them with wide-leg pants, skinny jeans, or bootcut jeans, and they will mesh effortlessly.”
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Budget-friendly doesn’t mean you have to sacrifice comfort. These are some of the highest-rated Chelsea boots on Amazon, and after spending a couple of weeks wearing them, we can see why. The boots are constructed from a water-resistant faux leather material, and they have a fantastic lug sole to prevent slipping and sliding in wet climates.
They have a snug fit, especially around the ankles, but this actually added some support around the ankle and calf. That said, if you’re planning long walks in these shoes, you may want to consider an insole — there’s not much arch support and the heavy heel can cause fatigue.
Sizes: 5.5–11 | Materials: Faux leather, thermoplastic elastomers | Colors: 7
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Timeless and versatile design
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Scuff-resistant
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High-quality construction
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They don’t rub or chafe the feet
These shoes are constructed from high-quality leather sourced from a Leather Working Group Certified tannery that doesn’t scuff and can withstand lots of wear and tear. They’re also relatively comfortable right outside of the box and don’t rub or chafe the feet when breaking them in. The premium leather is quite stiff though, which makes it a challenge to slip these on and off, especially with thicker socks.
The boots are also constructed with a memory foam insole and are said to have some shock absorption, but our tester didn’t think they had enough arch support and cushioning. Regardless, these boots last a long time and get comfier with each wear.
Sizes: 5–11 | Materials: Leather, memory foam, elastic | Colors: 3
Editors Say
“I’ve owned these boots for over a year, and the leather material is super high quality — it hasn’t scuffed at all despite walking the streets of New York.”—Madison Yauger, PEOPLE shopping editor
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Heavy lug sole with good traction
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Sturdy and fits true to size
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Tons of colors to choose from
Another gorgeous leather option, these boots are made with a durable leather and a heavy lug sole that has enough traction to keep you sturdy on your feet. They fit true to size, and there are a whopping 22 different colors to choose from, making it easy to find the perfect pair for your personal style. The boots’ durability and quality are definitely reflected in the price. They showed no signs of wear and tear at the end of the testing period. That said, those with wide feet may consider other pairs that don’t fit as tightly.
Sizes: 5–14 | Materials: Leather | Colors: 22
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Ugg is best known for its collection of suede and fur boots, but we were impressed with its Chelsea boots. They have a chunky rubber platform with a lug sole and ultra-durable leather uppers with a comfortable upcycled wool and lyocell insole. The materials and construction justify the cost, and these are fully waterproof, making them an ideal pick for rainy climates.
Plus, the boots are so sturdy and supportive, and the footbeds actually form to each foot’s shape with regular wear. Note: There’s a necessary break-in period and they can run narrow so wider feet may opt for other boots.
Sizes: 5–12 | Materials: Upcycled wool, lyocell, EVA, rubber, leather | Colors: 3
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Takes time to break in
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Snug toe box area
If you want the look of a fashion boot with the durability of a more functional style, go with this L.L.Bean boot. These leather boots have a timeless silhouette with a mid-calf shaft, flexible elastic gore, and high-quality leather construction. There’s also a rubber outsole with mini-lug VertiGrip, which is specifically designed to prevent slipping and sliding on several types of terrain.
There is a significant break-in time and the toe box fits snugly, but the EVA molded footbed ensures comfort. Plus, these boots are down to get dirty and can withstand lots of wear and tear.
Sizes: 6–11 | Materials: Leather, EVA, rubber | Colors: 3
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Timeless style
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High-quality design
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Cool pebble texture
Chelsea boots are a great shoe style to invest in since they never really go out of style, and the Reformation Katerina Lug Sole Chelsea Boots are a solid pick. These boots boast a high-quality design with durable leather uppers and a pebble texture for unique detailing. They’re also versatile enough to wear with casual leggings and oversized sweater looks, as well as dressier ensembles.
The only downside to these boots is the break-in period: The fit was initially super stiff and caused a lot of discomfort around our tester’s ankles and heel. However, with regular wear, the leather breaks in and the shoes grow more comfortable.
Sizes: 5–11 | Materials: Leather | Colors: 1
Editors Say
“Considering the brand and price, I definitely expected high-quality boots, and these are exactly what I imagined. I love the lug sole heel and black tumbled leather. The stitching is top-notch, and I can tell these will last for years of wear.”—Kayla Kitts, PEOPLE shopping editor
Others We Tried
Hunter Original Chelsea Insulated Boot: We loved the high-quality construction and ease of cleaning with these Hunters. They also have very reliable traction, which is ideal for the rainy conditions they are intended for. However, the boots take a long time to break in, and we felt like we were paying for the brand name rather than the design.
Quince Suede Chelsea Boot: Quince is a hot spot for budget-friendly, high-quality pieces, so we were excited to try these Chelsea boots. We found them quite stylish, supportive, and affordable, but the break-in period was a bit inconsistent, and we weren’t confident that they would last past a season or two of wear.
Soda Pilot Lug Sole Low Heel Chelsea Ankle Bootie: These Soda ankle booties are trendy and have a cool lug sole style, but after testing these for a couple of weeks, we found that the material was a bit too cheap for our liking and they aren’t as comfortable as they look.
People / Laura Gurfein
What to Know About Chelsea Boots
Material and Function
When shopping for Chelsea boots, you’ll want to consider the material of the shoe. “High-quality materials usually indicate that the shoe will last you a long time,” says Scratch. “The best material for Chelsea boots is leather or suede.”
However, the material used for the boot sole is equally important, according to Styless. “Boots with a rubber sole guarantee extra protection for the boot,” she says. Finally, considering function is also a good idea, explains celebrity wardrobe stylist Lunden Olin. “Function should always be a priority because no one wants their shoe falling apart after wearing them for a long time,” he tells PEOPLE.
Comfort and Fit
Like material, prioritizing comfortable pairs of Chelsea boots is equally wise. Since you’ll be walking in them, you’ll want to select a pair of boots that don’t strain your feet. To find a comfortable pair of Chelsea boots, Styless recommends paying attention to the sole. “The most comfortable Chelsea boot has to have a perfect sole,” says Styless. “This way, it does not irritate your foot when rubbing against the sock.”
Comfort also depends largely on the fit. And, according to Neely Woodson Powell is the founder of Charleston Shoe Company. “Chelsea boots should fit casually, comfortably, and effortlessly.” They’re a boot style that you should be able to break in (if necessary) and wear for years and years, so choosing a pair that fits well is key.
Reviews
Reading through user reviews lets you see all the ins and outs of the shoe before you buy, so you’ll know what to expect. “Shoppers should check online and see the reviews before buying Chelsea boots,” adds Styless. “This way, shoppers can be comfortable buying boots without regrets.” Pro tip: Pay attention to Chelsea boots with higher star ratings and plenty of user reviews — these usually indicate that the shoe will be a good match.
People / Kelli Bender
Behind The Scenes
To find the best Chelsea boots, we scoured the internet for top styles across a range of silhouettes and price points before narrowing it down to 11 top picks to try out. From there, our team spent two weeks and over 237 hours putting these selections to the test, carefully considering comfort, fit, quality, support, and value.
- Comfort: When testing Chelsea boots, we first considered the overall comfort of each design, including whether or not the boots were comfortable right out of the box, what the break-in process was like, and what kind of cushion the insole offered (if any).
- Fit: As with any shoe style, fit was also super important to us during the testing period. We slipped each pair on and took note on how they fit overall, whether or not they were true to size, and how the fit held up during the two-week period.
- Quality: Chelsea boots were initially designed with function in mind, and while many have become more fashion-forward over the decades, we still wanted to find options that were stylish and high-quality enough to last. With that in mind, we made note of any signs of wear and tea throughout the testing period.
- Support: Chelsea boots are by no means a running shoe, but they are meant to be worn while walking miles so they need to be comfortable and supportive. With this in mind, we considered the different support features offered and what they actually felt like when we slipped them on and walked around for miles (seriously — we traveled 76 miles during this testing period).
- Value: We’re all for investing in a good pair of boots, if the quality is there, so we also made a point to score each shoe style for their overall value and whether or not we thought they were worth the price point based on the above factors.
With all of these pillars top of mind, we carefully reviewed our notes and compared each shoe style tested to determine which shoes were worthy of our best of list.
Frequently Asked Questions
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Which brand is best for Chelsea boots?
It all depends on what you’re looking for, but one of our top-rated favorite pairs of Chelsea boots is the Blundstone Classic Chelsea Boot. This pair boasts a classic pull-on style with a high-quality and durable water-resistant leather that’s stain-resistant and easy to clean. Initially, the shoes fit snugly, but after a few wears they molded to the feet beautifully.
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Are expensive Chelsea boots worth it?
You may be on the fence about buying a pricer pair of shoes. However, splurging up does have its perks, as expensive shoes are designed with high-quality materials that are built to withstand years of wear, according to Scratch. “When you’re paying for an expensive shoe, I believe you’re paying for longevity,” Scratch tells PEOPLE. “You’re also paying for the quality of the shoe to last through any weather conditions.”
Why Trust PEOPLE?
Jessie Quinn is a contributing commerce writer for PEOPLE and has written for publications such as Byrdie, InStyle, The Spruce, NYLON, and more. When covering the best Chelsea boots, Jessie carefully reviewed the testers’ insights to learn more about their experiences with each style selected and how well the boots held up during the two-week testing period. She also connected with shoe expert Neely Woodson Powell to learn more about Chelsea boots and what to consider when shopping for the best designs. From there, Jessie compiled the PEOPLE team’s insights and organized their experiences into this best-of list.
Courtney Leiva is a contributing commerce writer for PEOPLE and has written for publications such as The Daily Beast, Buzzfeed, HuffPost, and more. Courtney spoke with fashion stylists to learn more about how to choose a pair of Chelsea boots and what standout features to look out for as you shop.
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