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Much like my favorite pair of worn-in Levi’s, Chelsea Boots are a mainstay of my wardrobe year-round. Pairing easily with dresses, jeans, and leggings alike, these short, slip-on boots are my closet chameleons because of their versatility. Named after the trendy Chelsea neighborhood in London—where they gained popularity symbolizing the groovy style of the 1960s—some believe the origins of the boots (sometimes called “paddock boots”) started way back with Queen Victoria who wanted an easy, lace-free, boot for horseback riding.
The Chelsea silhouette has evolved to now include all sorts of shapes and styles from sleek or chunky, to sporty or cowboy. Check out our top picks across categories perfect for all weather and all occasions.
How to choose the best Chelsea boots for women
While Chelsea boots come in a variety of silhouettes that make it relatively easy to find a style you gravitate towards, a few questions can help you winnow down your choices.
Where will you be wearing them?
Looking for work boots or hiking boots? Wearing these boots for long stretches of time or just out for the evening? In addition to looking cute, considering where you are going, and for how long you’ll be in them helps factor in important details like fit, style, cushion, and construction of your boots. There’s a big difference from being on your feet all day and shoes you’ll sport just for drinks.
What material works best for your lifestyle?
Construction, water-resistant, how they age, and how they hug and protect your feet are things you want to consider for shoes that will brave the elements. For rainboots look for waterproof leather or vulcanized rubber, and make sure seams look durable. For everyday work boots, opt for moisture-wicking insoles to keep hard-working feet dry.
What’s your budget?
What are you looking to spend? $50 or $500? Shopping for an investment piece, or something lower in price and heavier on trend you don’t mind wearing for a season or two? Do brand names matter to you? Asking these questions upfront will narrow your focus and keep you within budget. We all want to save money, but also keep in mind the quality of craftmanship. When in doubt check out reviews for info on comfortability and durability. Tip: Sign up for deals alerts at your favorite brands to score discounts, or check out our list of the best places to buy shoes online to track sales.
Our top picks for the best Chelsea boots for women
Best everyday Chelsea boots: Dr. Martens Women’s Work Boot
Classic, but with an edge, Dr. Martens are always good for making a statement. The Chelsea style of the brand offers a more streamlined look and wears well for work and weekends. While they’re not as comfortable as your favorite pair of flip-flops, consider these as easy to wear as your favorite running shoes. The non-slip soles and water-resistant leather makes these boats wearable year-round.
Specifications:
- Sizes: 5-15
- Colors: Black
- Material: Coated, full-grain leather
- Heel height: N/A
- Price at time of publish: $169
What we like:
- The rebellious feel of Docs
- Moisture-wicking insoles to keep hard-working feet dry
What we don’t like:
- They don’t come in half sizes, so most recommend sizing down
The bottom line:
These boots are super cool and comfortable for all day wear, and will last years.
Dr. Martens Work 2976 Chelsea SR Boot (Black) Work Boots
Best budget Chelsea boots: Dream Pairs Women’s Chelsea Booties
Coming in under $35, these top-rated (with nearly 2,000 four-star-plus ratings) are an Amazon bestseller. I like that these chunky, lug-soled boots look smart in addition to being comfortable and lightweight.
Specifications:
- Sizes: Size 5-11
- Colors: Black, chestnut brown, caramel brown, grey
- Material: Synthetic leather
- Heel height: 1.25 inches
- Price at time of publish: $43
What we like:
- All day comfort
What we don’t like:
- Synthetic material equals non-breathable
The bottom line:
Stylishly chunky yet lightweight, these are great shoes at great price.
DREAM PAIRS Womens Black Boots Chelsea Ankle Booties Shoes, Size 6, DAB213, Black/Pu
Best suede Chelsea boots: Sorel Women’s Hi-Line Chelsea Boot
Available in both waterproof suede and leather, the Sorel Women’s Hi-Line Chelsea boot comes in six eye-catching colors and keeps your feet dry in all weather, especially in snowy winter weather.
Specifications:
- Sizes: 5-12
- Colors: Grey, black, brown, blackened brown, sand, taupe, beige, reddish brown
- Material: Waterproof suede or waterproof full-grain leather
- Heel height: 1 inch
- Price at time of publish: $175
What we like:
- Ready to roll right out of the box—no break in time needed
What we don’t like:
- Reviewers say they can run narrow
The bottom line:
Well-made stylish boots perfect for hiking or commuting, even in snowy weather.
SOREL Hi-Line Chelsea Boot in Omega Taupe/Major at Nordstrom, Size 8
Best heeled Chelsea boots: Boden Block Heel Chelsea Boots
I usually shop Boden for my kids, but jumped on the bandwagon when I saw these beauties. Made from responsibly sourced leather, these elegant boots are perfect when you’re looking for a little height while still going easy on your feet.
Specifications:
- Sizes: 36-42 European, which translates to 5.5-9
- Colors: Black, ecru white, and honey brown
- Material: Leather upper
- Heel height: 2.75 inches
- Price at time of publish: $230
What we like:
- Nice lift but not too high, ideal with smart dress pants for work
What we don’t like:
- Doesn’t come in larger sizes
The bottom line:
The perfect fall boot—not too low, not too high, and works with a variety of outfits.
Block-Heel Chelsea Boots Black Women Boden
Most versatile outdoor Chelsea boots: Blundstone Women’s Classic 585 Chelsea Boot
These marbled brown boots by Blundstone are one of the iconic brand’s bestsellers. A pair of Blunnies are an investment that will likely last years, and this Chelsea style comes in a supple leather that forms to your feet, giving you a welcoming, worn-in feeling from the get-go, like your favorite pair of running shoes.
Specifications:
- Sizes: 6-11
- Colors: Rustic Brown
- Material: Water-Resistant Leather
- Heel height: N/A
- Price: $230
What we like:
- Pull-up tabs are clutch
What we don’t like:
- On the pricier side
The bottom line:
Classic rugged boot that will last through many seasons of wear.
Women's Classics Chelsea Boots, Rustic Brown #585
Best lug sole Chelsea boots: Everlane The Lug Chelsea Boot
Made in Brazil with sustainably sourced leather, these water-resistant Chelsea boots offer a chunky, lug sole that brings the right amount of attitude and protection from rainy weather. Not only are these boots functional, but fashionable, perfect for pairing with jeans and a sweater.
Specifications:
- Sizes: 5-11
- Colors: Black, beech green, and bordeaux
- Material: Leather
- Heel height: Not available
- Price: $235
What we like:
- I love how Everlane details how much it costs to make each shoe
- Beautiful color choices
What we don’t like:
- I’d like to see these in more classic brown
The bottom line:
A chunky boot to add some edge to your outfit, but also functional thanks to water-resistant materials.
Lug Chelsea Boot by Everlane in Bordeaux, Size 5
Best zip-up Chelsea boots: Cole Haan River Chelsea Bootie
I love the look of these pointed-toe boots that are a throwback to the sleek 60s style. In three stylish colors, the block heel gives a little boost to your height and are the ideal walking shoes for women.
Specifications:
- Sizes: 5-11
- Colors: Black, brown, and white suede, also available in waterproof bloodstone leather, black leather, sequoia leather, dark pavement suede, waterproof birch suede
- Material: Leather upper, suede
- Heel height: 1.5 inches
- Price: $180
What we like:
- The pull tab at back helps with putting on
What we don’t like:
- Zip-ups add an extra step
The bottom line:
A stylish zip-up boot to take your outfit to the next level, available in a variety of colors and materials.
Cole Haan River Chelsea Bootie (Sequoia Leather) Women's Shoes
Best luxury Chelsea boots: Loeffler Randall Raquel Pull-On Boot
At almost $500, you’ll want something special, and these small-batch boots are it. We have been long-time fans of this women-owned brand that started in Brooklyn, and these woven leather Chelsea boots feature a padded footbed and roomy round toe for extra comfort.
Specifications:
- Sizes: 5-12
- Colors: Espresso brown, cacao
- Material: Leather
- Heel height: 1 inch
- Price: $450
What we like:
- The sophisticated woven pattern that will turn heads
What we don’t like:
- The Vachetta cow leather needs extra care
The bottom line:
The ideal blend of trend and quality that will never go out of style.
Loeffler Randall Raquel Espresso Pull-On Boot
Best Chelsea rain boots: Hunter Women’s Original Chelsea Boots
These classic Hunter Women’s Original Chelsea boots come in short Chelsea style in a variety of their signature colors. The vulcanized rubber means they are super elastic and weather-resistant, making them the perfect boots for a rainy day. Shopping tip: The Hunter Chelsea boot also made our list of the best Chelsea boots for men.
Specifications:
- Sizes: 5-11
- Colors: Navy, black, hunter, olive, grey, chocolate, red, white
- Material: Natural rubber
- Heel height: N/A
- Price: $135
What we like:
- Supportive footbed
- Fun, stylish colors
- Waterproof
What we don’t like:
- No half sizes available
The bottom line:
One of the most famous rain boot brands offers a trendy and durable twist with a Chelsea boot that comes in a variety of color choices.
Hunter Boots | Women's Original Chelsea Boots 11 Navy
Best white Chelsea boots: Madewell The Wyckoff Lug Sole Boot
You can count on Madewell for reliably stylish basics for everything from weekender bags to loafers for women. Their take on Chelsea boots, in statement-making white, is no exception. These chunky, leather lug soles offer their signature “Cloudlift padding” for longtime wear.
Specifications:
- Sizes: 5-12
- Colors: White, brown, and black
- Material: Leather lining and upper
- Heel height: 1.5 inches
- Price: $198
What we like:
- The black elastic panels give cool contrast
What we don’t like:
- The lug sole is trendy and offers support (while also keeping you steady in slippery conditions), but it may not fit in with work clothes if you’re looking for something you can wear to the office
The bottom line:
You’ll stand out in these comfy, distinctive boots that have an on-trend lug sole.
Madewell The Wyckoff Chelsea Lugsole Boot in Leather (Pale Parchment) Women's Boots
How we selected the best Chelsea boots for women
There are so many styles of Chelsea boots, we worked across categories and styles, and checked out reviews, “best-of” list’s, and asked our own editors for their favorite brands.
Frequently asked questions (FAQs)
What are Chelsea boots?
Chelsea boots are recognizable as short, pull-on boots with elastic panels or gussets . Some point to the Beatles for popularizing the snug boots in the 1960s. They’re named after a popular neighborhood in London.
How to wear Chelsea boots?
There are many ways to wear Chelsea boots, but some popular pairings are chunky lug soles with dresses, high heeled with jeans, and sporty with just about everything! They add a statement to any outfit from casual, to formal.
Are Chelsea boots flattering?
Yes, Chelsea boots are pretty flattering across the board. Due to their snug construction, it’s good to try them on for fit—or size up—if you have a wider foot or plan to wear them with thick socks.
Are Chelsea boots work appropriate for women?
Of course, it depends on your employer's dress code, but for the most part, certain styles can work for workwear. Some Chelsea boots are sleek and come in soft fall tones, perfect for pairing with a daytime look like a dress or work pants and a nice top. Chunkier styles may work in creative offices, but feel too casual for more buttoned-up workplaces.
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