This magical boot is filled with (unique) full historical significance. But that doesn’t mean it belongs in the antique category. In fact, it is far from it. Our top shoe brands reinvent the seasonal trend with contemporary takes that contrast classic silhouettes.
Born at the direct request of Queen Victoria, Chelsea boots have since made their way into celebrity circles. And while the Queen considered them a functional necessity for long days on horseback, the Beatles and the Rolling Stones made them famous fashionistas. We can’t help but agree with both sides. Named after the city of London, Chelsea boots are still loved around the world for their comfortable yet stylish nature.
These Ankle Boots stand out with flexible side panels for easy on and off (say goodbye to boring laces). Although pull-ups completely remove all the hassle. And the grooved rubber soles aren’t just stylish boots, they’re made to last a lifetime. But beyond these iconic features, these women’s slip-on boots come in all shapes and sizes. And our best shoe brands always surprise us with the latest models.
Anine Bing screams trendy style and you’ll hardly miss out on these Cuban heels. Although Koio considers it sophisticated and respects traditional design. Dr. Martens also added Chelsea to his repertoire. And White House Black Market knows how to take your outfit to the next level in every sense of the word. All in all, it’s hard not to fall in love with each of these brands because of their unique Chelsea boot. And we’re pretty sure your perfect match is on the way.
- Rubber sole
- Imported
- Heel measures approximately 1″
- Elastic goring
- Made in the USA or Imported
- Polyvinyl Chloride sole
- Chelsea boot style
- Elastic gussets
- 100% Black smooth leather
- Imported
- Synthetic sole
- Heel measures approximately 1″
21 Best Chelsea Boots for Women
1. Koio: Best overall women’s Chelsea boots
About this Item
- Steve Madden Womens
- Women’s heeled ankle boot
- Lug sole and knit fabric material elevate this ankle boot
- Back pull tab and stretch material for easy on and off
- Approximately 2.25″ chunky heel
They are versatile. They are nice. And they are stylish. The waterproof tank sole, handmade in Italy, is light on the feet. And it gives a timeless shoe a modern touch. Flexible side panels provide ample stretch. The elegant black shade complements any ensemble.
These Koio Chelseas are more than just a wardrobe. They are perfect for any occasion.
2. Isabel Marant Castay: Best designer Chelsea boots for women
About this Item
- Made with our Arcadia Leather—a classic high-shine rub-off leather with a two-tone effect created with a special treatment to reveal contrast color, particularly in the toe area
- Built on the iconic Dr. Martens air-cushioned sole
- Chelsea boot style
These timeless Castays easily beat the seasonal trends with their classic style. And we don’t think you could use a rubber sole even if you tried. The black leather has a subtle sheen that contrasts with the thicker shoe. And there’s nothing a simple yet stylish silhouette can’t achieve when it comes to complementary footwear.
These Chelsea boots will decorate your designer jeans with the same subtlety as your clothes. And they’ll expand your fall wardrobe in quintessential Isabel Marant style.
3. Dr Martens: Best value women’s Chelsea boots
About this Item
- Pull-on Chelsea boot style
- Wyoming is a rich leather with a subtle grain and oily surface.
- Built with core Dr. Martens DNA: grooved edges, an AirWair heel loop and visible stitching
- Model Number: 26002001
- Care Instructions:Wipe away dirt using a damp cloth, allow to dry apply a clear wax based shoe polish to restore shine as desired.
Famous for their chunky black boots, Dr. Martens does it again with this flexible, laceless version of the old-school classic. Born in 1461, the timeless brand is certainly not new to the shoe game. And their durable designs allow them to be passed on to future generations. Although the iconic label features the famous logo, we’re pretty sure you’ll spot the brand’s classic silhouette from miles away.
These Chelsea boots have the same great look as their laced counterparts. But they offer new functionality in an effortlessly smooth style.
4. M.Gemi The Noemi: Best leather ankle boots for women
About this Item
- Core Comfort Technology
- Elastic goring
- Faux leather Lining
- Closure type: Pull-on
Proof that you get the best of both worlds, Noemi combines outdoor activities and everyday elegance. The tab ensures seamless sliding. The Italian artisanal quality synonymous with M.Gemi is encountered every day on foot.
This slightly lower ankle boots adapt perfectly to any foot shape. And this M.Gem Chelsea offers that extra spring feeling (yes, even in the colder months).
5. Legres Garden: Best women’s Chelsea boots for walking
About this Item
- Sam Edelman’s Iconic Laguna Chelsea Boot
- A heavily lugged sole with a utilitarian style update to a classic Chelsea boot. The LAGUNA offers wateproof technology to take you through the day
- This pull-on Chelsea boot is perfect for work & play. Pair this comfortable waterproof boot with denim, dresses or leggings
- Heel Height: 1.5 inches
- Boot Shaft: 5.75
- Boot Leg Circumference: 9.45 inches
These boots are made for walking. The ’96 hit single is said to refer to this pair of anklets.
Alright, we figured it out. But you’d think so too when you’ve spent a day on the town here in Chelsea. Celebrating the rich history of Italian craftsmanship, usability has never been more perfect. The soft leather fabric comes with a side rib for added flexibility. And sturdy soles never get old.
With these comfortable Chelsea boots from Legres, a stylish ride through the cobbled streets of Paris feels like a walk in the park.
6. Anine Bing Roy: Best cowboy-style Chelsea boot for women
About this Item
- Steve Madden Womens
- Women’s heeled ankle boot
- Lug sole and knit fabric material elevate this ankle boot
- Back pull tab and stretch material for easy on and off
- Approximately 2.25″ chunky heel
Try something different this season with Anine Bing’s cowboy version of classic Chelsea. The elegant Roy boot respects both styles in a harmonious and comfortable way. The drawstring and flexible sides refer to the Chelsea style. When a thin shoe is ready, take your wardrobe to the next level with a chunky Cuban heel. The western silhouette hits just above the ankles for an elongated feel.
7. Blundstone BL510 Original 500: Best Chelsea work boots for women
About this Item
- Weather-proof leather 2.5mm thick with Shock protection system (SPS)
- The size on the shoe is the AU Size, Please refer to the size chart for conversion
- Removable comfort footbed
- The sizes available in drop down are for US Men’s, refer sizing chart for Women’s
Double pull-up tags mean double the fun. They are protective shoes perfect for outdoor use. But they also take you out for after work drinks with an edgy attitude. Durable outsoles are made for any pad or trail. And the waterproof leather keeps whimsical weather a problem. Shock absorbing midsole provides a softer landing. And the dark neutral color scheme speaks of modern and versatile functionality.
So whether you’re camping with them for the weekend or celebrating the weekend with a glass of wine, these gorgeous boots will be your new best friend.
8. Frye Sabrina: Best brown Chelsea booties for women
About this Item
- Frye and Co. is a curated Collection of artisan-inspired, of-the-moment styles designed for the spirited adventurer who craves distinctive styling and incredible comfort. Live. Love. Explore. #Lets just go
- Made from vintage leather, the ‘Caden Bootie’ is shaped with an artisanal stitch at the V cut-out and finished with a covered zipper closure.
The soft, handmade brown leather gives the classic silhouette a rustic look. And if you’re looking for a cool step to face the winter, these chunky heeled beauties (slippers) know how to do it. Pair them with light floral prints or slimmer jeans. The neutral color scheme always adds a subtle sophistication.
And these brown raised boots are for you (call the Pumpkin Spice Latte!)
9. Proenza Schouler: Best women’s chunky boots
About this Item
- Rubber lug sole
- Waterproof leather, Elastic gores, Pull tabs
- Heel: 1.5in / 40mm
- Platform: 1in / 25mm
- Leather lining
Proenza Schouler knows how to take the latest trends to new levels. And this sturdy pair is no exception. The ankle silhouette is accentuated by an asymmetrical toe. And the (extra) thick sole definitely makes a statement (be prepared for compliments).
Grab a pair of these bold black boots for a stylish look. Or opt for a white model to truly impress in classy environments.
10. Gucci: Best luxury Chelsea boots for women
About this Item
- Steve MaddenChelsea ankle boot with removable jewel strap
- Comfortable unit bottom
- Elastic side panels
- 2 inch chunky heel
You don’t have to wear accessories when wearing these cool Gucci. A detachable ankle strap embellished with sparkling crystals does it all for you. Unique gems resemble vintage gems. And they speak of the timeless modernism that characterizes a luxury brand.
These luxurious details contrast perfectly with the Chelsea rim sole for refined yet fierce sophistication. While the Double G signature is all you need to complete the glossy black look.
11. Toteme: Best black Chelsea booties for women
About this Item
- Pull-on design with goring side panels.
- Rounded toe.
- Rear pull-tab offers easy entry.
- Breathable man-made lining.
- Cushioned footbed
- Low block heel.
The simple silhouette is characterized by a pointed pointed tip. The elegant black leather gives a subtle sheen to the exquisite design. They add a versatile touch to any outfit and you’ll find it hard not to wear them every day.
These timeless Chelsea Totemes are here to stay. And there’s no better time to buy a couple than now.
12. WHBM Military Bootie: Best heeled women’s Chelsea boots
About this Item
- Stackled Block heel boots
- Side Zipper construction
- Synthetic material
- 1.5″ heel
- Cut-out details.
Comfortable heels – no oxymoron when wearing WHBM military boots. And we’re pretty sure you’ll agree with us when you can roll on the cobblestones without worry.
This simple silhouette finds its voice in crisp details, like the dominant presence of military-inspired metal buttons and a stiletto heel. Pair these comfy WHBM Chelsea boots with red lips and you’ll feel as confident as a million dollars.
13. Tod’s: Best suede leather ankle boots for women
About this Item
- Tod’s – Model number: XXW17B0Z770HR0B999
- Authentic Tod’s® brand new Guaranteed
- Free shipping, free return, Tax free.
- Delivery in 2/3 working days.
- Designed and Made in Italy
The best booties come in all shapes and sizes. This comes in the form of a velvet suede Chelsea boot. The abundant production of the typical design speaks to the luxurious reputation of the brand. And the versatile style means you can wear the same pair every day of the week (hello capsule wardrobe!).
Pair these Chelsea Tod’s in black with neutral or bright tones for any look. These adaptable boots facilitate layering by completing each part of the ensemble.
14. Saint Laurent Theo: Best suede heeled Chelsea boot for women
About this Item
- Latest Fashion and Trend for Stylish and Sexy look
- Ankle Bootie on a LUG SOLE STACK BLOCK heel (approximate 3.5” height)
- Cute and comfortable Ankle Bootie. * Wide stretchy elastic side panels gore for easy in and out
Wake up feeling depressed. Put on suede (black) shoes and make your day a catwalk. These chunky heels are sure to take your outfit to new heights and boost your confidence. Suede fabric speaks of refined sophistication. And toes keep everyone around you in check.
These delicious Chelseas are perfect companions for public speaking, first dates, or anything else you can do with an extra lift.
15. Elleme Chouchou: Best white Chelsea boots for women
About this Item
- Latest Fashion and Trend for Stylish and Sexy look
- Ankle Bootie on a LUG SOLE STACK BLOCK heel (approximate 2” height)
- Wide stretchy elastic side panels gore for easy in and out
- Cute and comfortable Ankle Bootie, Platform measures approximately 1″, Shaft measures approximately 4”
We all know the devil is in the details. But Chouchou details are the holy grail of luxury design. And this white leather pair couldn’t be better. The clear color scheme is complemented by a subtle heel with frills and accents. The extended elastic sides still use the classic Chelsea elastic. And the thick rubber lining exudes a playful yet (uniquely) full-bodied attitude.
These decadent details are enough to make any fashionista fall in love with this pair of Chelsea designers. We know we are.
16. Gianvito Rossi: Best cream women’s Chelsea boots
About this Item
- Rubber lug sole
- Waterproof leather, Elastic gores, Pull tabs
- Heel: 1.5in / 40mm
- Platform: 1in / 25mm
- Leather lining
I am your new mom jeans partner in casual chic day style. The soft cream color is a perfect contrast to the sturdy edges and thick base. The climax is a masterpiece of brutal feminine minimalism. Made in Italy, the beige calfskin silhouette extends above the ankle. It slips thin under your looser jeans. And the stretched elastic panels make it easy to put on.
Following in the footsteps of his father Versace, this Chelsea pair is proof that Gianvito Rossi (pun intended) successfully struck out on his own.
17. Nisolo Everyday: Best women’s tan Chelsea boots
About this Item
- Origin Made in the USA or Imported
- Sole Material Rubber
- Shaft Height 4.5 Inches
- Outer Material Suede
Short but sweet: This brown pair would melt your leather-loving heart. The light honey shade is perfect for any outfit. They add a sophisticated touch without stealing the show. And the lower ankle is flattering for every type of foot. But soft, fat boots are more than just a fashion statement. All of their leather comes from sustainable sources. And ethical footwear is at the forefront of the sustainable brand.
This versatile pair of Chelsea boots is infinitely functional with waterproof leather and neutral tones.
18. Valentino Garavani: Best platform Chelsea boots for women
About this Item
- Retains classic Doc’s DNA, like grooved sides, visible stitching and scripted heel-loop
- Good slip resistance and abrasion
- Constructed on the iconic, durable Dr. Martens air-cushioned sole
- This is a Goodyear-welted product
Extra height? Check. All day comfort? Yeah! What more could you want from a Chelsea couple? Described as jet-set chic, this Italian brand knows how to make a statement with bold strokes. And these huge bases are great examples. Although the rest of the shoe is relatively simple.
This black leather silhouette tops our list of the most comfortable boots for women. And at the same time, they are guaranteed to receive a lot of compliments.
19. Bottega Veneta: Best lug sole Chelsea boot for women
About this Item
- Sam Edelman’s Iconic Laguna Chelsea Boot
- This pull-on Chelsea boot is perfect for work & play. Pair this comfortable waterproof boot with denim, dresses or leggings
- Heel Height: 1.5 inches
- Boot Shaft: 5.75
- Boot Leg Circumference: 9.45 inches
Thanks to the thick rubber and deep notches, the button soles are characteristic of the iconic boot. But some do it better than others. And this Bottega Veneta happens to take the cake. Strong soft Italian leather is available in deep green, brown and black. And while all classic colors are great, you can never go wrong with black.
These comfortable Chelsea boots from Bottega Veneta feature double pull-up tabs and elongated elastic panels for easy on and off.
20. Blundstone #1477: Best waterproof women’s Chelsea boots
About this Item
- Fabric Type 100% Leather
- Origin Imported
- Sole Material Synthetic
- Shaft Height 3 Inches
It’s a one-time purchase that will make the rest of your life a lot easier. These Blundstone antiques make outdoor activities effortless. They are made for long days. And they’re ready to handle anything thrown at them, including heavy rains. Dark brown leather adds masculinity to an otherwise feminine silhouette.
These spicy Chelseas can have a vintage flair. But they are designed with the latest technology to make every step luxurious. We consider them a pair of complete opposites.
21. Ganni: Best women’s chelsea rain boots
About this Item
- Fabric: Matte PVC
- Heel: 1.5in / 41mm
- Platform: 1in / 25mm
- Elastic at side
- Rain boots
These beautiful sturdy soles are the ultimate rain boots. They are made of durable, waterproof rubber and designed to withstand all weather conditions. The multifunctional boot shows off all sides of your Chelsea. But the contemporary brand has added a modern twist. The silhouette is slightly taller and is available in stylish black or muted green.
These versatile Ganns are designed for the rain. But we give you full permission to use them even in bright sunlight.
Women’s Chelsea Boots Buying Guide
What are Chelsea boots?
Chelsea boots were born out of the need for comfortable riding boots (from Queen Victoria herself). And they quickly became a timeless trend to steal the show (boat) season after season. They embody our functional fashion mantra in every aspect of a casual and chic style. And even if they are no longer seen on the side of the horses, this British design is moving almost everywhere.
These boots are distinguished by a rubber sole and flexible side panels, so they can move with ease. They gave up on the effort to record. And the tabs are used to shape the flexible shoe well on your foot. A slim silhouette usually stands out from thick soles. And the woman-man collaboration can be seen as a classic-modern masterpiece.
But as with all models, no two Chelsea are alike. Some rise above the ankle. And others keep it short and sweet. A little air on the side of elegant simplicity. Others exude a cheeky chic attitude with exaggerated soles. To see which pair fits your style, continue reading our full list of the best Chelsea boots in the business.
How to match chelsea boots?
Chelsea boot dresses come in all styles and variations. Versatile boots can be worn over skinny jeans. Or hide under mom’s jeans. They can be combined with babydoll dresses in daylight. And in the evening they easily fit into a luxurious and fitted dress. They are perfect for the office with sophisticated insoles.
Black Chelsea can be seen as the equivalent of white sneakers. The similarity is that you can wear them with anything. And in this case they are your black canvas on which to admire your creativity. Or drop them if you run out of ideas. Finally, you can choose exactly how to wear your Chelsea boots. And it’s usually hard to go wrong. If you don’t know where to start, pair them with a dress for the modern classic look we love.
Frequently Asked Questions about Women’s Chelsea Boots
Which brand is best for Chelsea boots?
Most of our top shoe brands feature a unique take on the classic Chelsea. Anine Bing added a western twist with cowboy Chelseas. Ganni took functional fashion to new heights with extreme wellies. And as expected, Gucci has added its glamorous touch of vintage pearls to create a sparkling show. Read our full list of the best Chelsea boots for more inspiration.
Will Chelsea boots still be in fashion in 2022?
Chelsea boots are definitely still in fashion in 2022. In fact, we don’t think the timeless boot will ever go out of style. Chelsea boots outfits change constantly with the seasons. Even if the shoes themselves always know how to adapt to changing trends. Choose a more classic pair to honor their story. Or boldly opt for a contemporary masterpiece that proves the iconic boot has been modified but never laced.
Is the Blundstone a Chelsea boot?
Blundstone can be more difficult than most. But with the signature tabs, stretch panels and welt soles, they’re definitely still Chelsea. In fact, they are the perfect example of a couple who are comfortable with everything. They’re stylish enough to hit the high-end streets. But sturdy enough to withstand all weather conditions.
What color are the best Chelsea boots?
We are biased towards more neutral shades when it comes to Chelsea boots. You can’t wear them with anything at any time. But the muted shades complement the iconic classic style. If we really had to choose a color, we would usually choose black. You can’t go wrong.
