10 Women’s Chelsea Boots to Shop Now

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Updated on January 29th, 2024

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Fall is a-coming and so it may be time to upgrade your footwear. The high-end labels will have you wearing stilettos and furry heels, but really? Those aren’t great for workdays or errand days. So I’m suggesting an investment in a more wearable shoe this season: the Chelsea boot.

Women’s Chelsea boots are convenient and stylish. They’re also very easy to find. You can shop Chelsea boots for women on DSW, Zappos, Amazon, and countless random shoe stores.

Read on to learn more about this style, why you might love owning a pair, and 10 styles to shop now.

Women’s Chelsea boots 101

How to spot a Chelsea boot? The style is most easily recognized by the elastic panels that sit on either side of the boot’s shaft. Those elastic sections deliver some truly useful benefits. For one, you can slip the boot on and off without having a personal assistant help you. Two, you get a snug ankle fit (so you don’t look like you’re standing in a pair of empty buckets).

And finally, those elastic panels add a fun mixed media vibe to your footwear.

Other characteristic features of the Chelsea boot include a pull tab at the back of the shaft, an embellishment-free design, and the super versatile ankle height.

That’s not to say all Chelsea boots look the same, though. You can find them in varying colors, materials, and heel heights.

A short history of Chelsea boots

The boot takes its name from London’s Chelsea neighborhood. Chelsea is home of King’s Road, a popular street that spawned plenty of fashion trends and designer names in England’s Victoria era and beyond.

In the late 1800s, men and women wore Chelsea boots as traditional garb. From those early days, Chelsea boots were popular for both casual and formal occasions.

Some 100 years later, Chelsea boots came back to mainstream fashion — and in a big way. Why? Because The Beatles and The Rolling Stones wore Chelsea boots. The masses, of course, followed suit.

Since the 1960s, Chelsea boots for men and women have been on and off the runways. But that only means the sleek, minimalist boot has earned classic status. So while the feeds may not be overrun with Chelsea boots today, you can confidently wear this style now and for seasons to come.

Of course, if you prefer a shoe that’s very current, you have that option. Look for:

Women’s Chelsea boots in colors other than black or brown
Boots that substitute rubber construction for leather in a stab at rain-friendly iterations
Chelsea boots with lug soles and contrast stitching
Hybrid styles that take the classic Chelsea elements and add embellishments

10 best women’s Chelsea boots

Now for a look at this season’s best Chelsea boots for women. All are conveniently available on Amazon.

1. The lug

Vepose Women’s Black Chelsea Ankle Boots, Lug Sole Fashion Elastic Short Pull on 9608 Booties, Size 9M US, (CJY9608 Black 09)

Please Note:IF YOUR TOES PART ARE…
Chelsea Style:Bilateral elastic…
Non-Slip:The special pattern on the…
Versatile Style:It can match with…
Comfortable:Women’s ankle boots…

See details on Amazon

This style blends an edgy lug sole with the classic elements of a traditional Chelsea. Wear these with cuffed or cropped jeans or, if you dare, a short skirt. You could also experiment with leggings and a long coat.

2. The everyday

Thursday Boot Company Women’s Duchess Chelsea Ankle Boots, Dark Olive Suede, 8

THE PERFECT FIT – We recommend…
THE DUCHESS CHELSEA BOOT – The…
UNPARALLELED WORKMANSHIP – Genuine…
THURSDAY’S SIGNATURE CRAFTSMANSHIP…
CLASS OF ITS OWN – We make zero…

$160.00 See details on Amazon

Streamlined and simple, Thursday Boot Company’s Duchess Women’s Chelsea Boot embodies the classic Chelsea style. You can choose from nine colors, but I love this Dark Olive Suede. The texture adds interest and the neutral color delivers great versatility.

3. The rain protector

Sale TOMS Women’s, Dakota Boot

Water-resistant leather uppers
Pull on style featuring dual gore…
Built-in OrthoLite Eco X4…
EVA midsole
Stacked leather heel

$111.91 See details on Amazon

Tom’s Dakota boot is available in water resistant black leather with a rubber sole. The tan strip at the base of the boot sets this style apart from the rest.

4. Winter white

Jeossy Women’s 9605 Chelsea Ankle Boots White Slip on Short Booties for Women Size 7(DJY9605 White 07)

Material:Synthetic leather and…
Insole:Soft insole that snuggles…
Cloure:These slip on chelsea ankle…
Occasion:The short boots suitable…
Size: Heel Height: 2.24″, Platform…

See details on Amazon

The Jeossy white women’s Chelsea boot looks suspiciously like Dr. Martens unisex Chelsea boot of the same color. Jeossy’s is the budget version, of course, made with synthetic leather and white stitching. The Docs are real leather with yellow stitching.

5. Faux furry

Sale Dr. Martens Women’s Leonore Burnished Wyoming Leather Boot, Black, 5 Medium UK (7 US)

Constructed for comfort on the…
This boot is Goodyear-welted,…
Good abrasion and slip resistance
Lined with warm faux fur
Retains essential Doc DNA, like…

$99.27 See details on Amazon

Speaking of the world’s most famous shoe doctor, Dr. Martens Leonore Chelsea incorporates one of the season’s hottest shoe trends: fur. Faux fur lining keeps your ankles toasty, while a thick sole distances you from ground water.

6. For the office

Marc Fisher LTD Alva Medium Natural 8 M

The versatile Marc Fisher LTD Alva…
Available in leather or suede upper…
Please note: upper material is…
Pull-on design with dual side…
Rear pull-tab for easy entry.

See details on Amazon

Add a heel and a pointed toe and the Chelsea boot could be the MVP of your work wardrobe. Go with classic black or choose one of 10 other colors, including a gorgeous camel.

7. The cowboy Chelsea

Teva Women’s Anaya Chelsea RR Boot, Bison, 8

Microfiber lining for a soft and…
Elastic gore stretches with your…
Metal shank stabilizes and supports…
Rubber outsole for durability and…
Best for: all weather city wear

See details on Amazon

Teva’s boot has an on-trend cowboy boot vibe, plus microfiber lining and a rubber outsole for comfort and durability.

8. Sock-inspired

Sale Athlefit Women’s Chelsea Boots Fall Platform Ankle Boots Slip on Chunky Lug Sole Boots

【FEATURES】: The boots feature a…
【DESIGN】: A unique combination…
【MATERIAL】: Use leather/suede…
【NON-SLIP】: These fashion lug…
【OCCASION】: Our chic chelsea…

$37.99 See details on Amazon

A sock boot and a Chelsea boot in one. Your ankles stay warm and you’re super chic in a pretty pair of light tan boots, for a wallet-friendly price. It doesn’t get much better.

9. Sleek easy

Dr. Scholl’s Shoes Womens Teammate Slip On Chelsea Dress Ankle Boot, Black Smooth, 7 US

A womens ankle bootie with faux…
A dress ankle bootie for women with…
Fashion dress boots for womens with…
Be Energized insole with all-day…
Flexible, durable sole

$100.00 See details on Amazon

Dr. Scholl’s style doubles down on sleek styling, with smooth faux leather and a minimal sole. Have fun dressing this shoe up or down as your calendar demands.

10. Taupe terrific

Juliet Holy Womens Chelsea Boots Fashion Winter Pointed Toe Chunky Stacked Low Heel Slip On Ankle Booties

【Measurement】:The boots heel…
【Material】: Faux leather and…
【Convenient Side Elastic…
【Low Stacked Block Heel】: The…
【TIPS】:These boots for women…

See details on Amazon

Juliet Holy’s women’s Chelsea boot is also understated, but it comes in this lovely faux suede taupe. Reach for these to complement nearly any outfit palette.

Chelsea boots: A cool-weather classic

Whether your signature style is always on-trend or classic, there’s a pair of Chelsea boots out there for you. Have fun shopping and styling the only boot that was equally loved by Brits in the Victoria era and rock-n-roll fans of the ’60s.