Step Into a Pair of Cute, Comfy Chelsea Boots This Season

best chelsea boots for women
Step Into a Pair of Cute, Comfy Chelsea BootsTimberland / Frye


"Hearst Magazines and Yahoo may earn commission or revenue on some items through these links."

Everyone loves a versatile boot, and of all the best boots for women out there, Chelsea boots are some of the best at combining style with function. Part of their appeal is that they’re so easy to slip on and off—no laces required. That of course, makes them very comfortable to wear, not to mention that they are just plain fashionable! So, if you're looking for an easy-to-wear pair, we've rounded up the best Chelsea boots for women.


What exactly are Chelsea boots, you may ask? They're characterized as being ankle boots with an elastic side panel. They date back to the Victorian era when the first pair was made by J. Sparkes-Hall for Queen Victoria, but they left the biggest footprint in 1960s Britain when members of the Rolling Stones and the Beatles were spotted sporting this style around London. They are versatile for everyday wear because they go with everything from your favorite jeans and sweaters to a cute dress and denim jacket.

Today, there are numerous variations of the style: leather, suede, or even waterproof rain boots depending on your lifestyle and activities. Plenty have thick rubber soles for stability and traction, making some of them the best walking shoes, too, no matter the weather. Dress them up, dress them down—either way, these boots are made for walking in comfort and style, so find your dream pair now!

Women's Cortina Valley Chelsea Boot

With a comfort sole, sturdy traction, and a classic look, Timberlands are made to last. With seven different colors to choose from, it will be hard to not buy more than one!

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.timberland.com%2Fen-us%2Fp%2Fwomen%2Ffootwear-10096%2Fwomens-cortina-valley-chelsea-boot-TB0A41EW929&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Women's Cortina Valley Chelsea Boot</p><p>$160.00</p><p>timberland.com</p><span class="copyright">Timberland</span>

Nine West Danzy Bootie

While a pointed-toe shoe isn't for everyone, they sure do make a shoe look super chic! They have the perfect heel size to give you a little lift while still maintaining comfort.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.dsw.com%2Fen%2Fus%2Fproduct%2Fnine-west-danzy-bootie%2F544644&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Nine West Danzy Bootie</p><p>$138.99</p><p>dsw.com</p><span class="copyright">DSW</span>

Dr. Scholl's Teammate Ankle Boots

Dr. Scholl’s is known for combining comfort and style for people who are on their feet all day (the comfort is real). The subtly western-style booties have the perfect heel height for any occasion and come in black, too.

<p><a href="https://www.amazon.com/dp/B07R1CBST7?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Dr. Scholl's Teammate Ankle Boots</p><p>$76.79</p><p>amazon.com</p><span class="copyright">Amazon</span>

Women's Greenwich Bootie

These classic Chelsea boots go with nearly any outfit! You can style them with a pair of skinny jeans, work slacks, or dresses. They’re great for city or country living, because they’re water resistant and feature a comfortable lug sole.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.colehaan.com%2Fwomens-greenwich-bootie-chestnut-leather%2FW24533.html&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Women's Greenwich Bootie</p><p>$69.97</p><p>colehaan.com</p><span class="copyright">Cole Haan</span>

Dolce Vita Stormy H20 Rain Boots

Say goodbye to clunky rain boots! These Chelsea boots will definitely keep your feet dry while keeping you in style. Plus, they come in three colors!

<p><a href="https://www.amazon.com/dp/B099NT1JYG?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Dolce Vita Stormy H20 Rain Boots</p><p>$70.66</p><p>amazon.com</p><span class="copyright">Amazon</span>

Steve Madden Amulet Chelsea Boots

Black and white is a classic color combo! These boots are the perfect way to show off that look, and they feature a removable jewel strap.

<p><a href="https://www.amazon.com/dp/B08WHXZRGH?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Steve Madden Amulet Chelsea Boots</p><p>$37.00</p><p>amazon.com</p><span class="copyright">Amazon</span>

Sam Edelman Chelsea Boots

These light brown Chelsea boots offer a nice change from the sea of black boots (which are obviously always in style). They're also water proof without the extra weight of wearing a rain boot.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.zappos.com%2Fp%2Fsam-edelman-laguna-black-2%2Fproduct%2F9461812&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Sam Edelman Chelsea Boots </p><p>$170.00</p><p>zappos.com</p><span class="copyright">Zappos</span>

Frye Sacha Chelsea Boots

Even though these boots are black, they're anything but ordinary! Frye combines Western and Chelsea styles to create this sleek, day or night boot. Crafted from soft Italian leather, these boots come in black or tan and feature the option to add a waterproof balm to your order.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.thefryecompany.com%2Fproducts%2Fsacha-chelsea-3470520-70520-black&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Frye Sacha Chelsea Boots</p><p>$177.98</p><p>thefryecompany.com</p><span class="copyright">frye</span>

Sorel Ainsley Chelsea Boots

These leather Chelsea boots are stylish and waterproof. They also have a removable memory footbed and a very slight heel.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.zappos.com%2Fp%2Fsorel-ainsley-chelsea-black%2Fproduct%2F9268432&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Sorel Ainsley Chelsea Boots</p><p>$150.00</p><p>zappos.com</p><span class="copyright">Zappos</span>

Soda Pilot Chelsea Fashion Boots

These chocolate brown boots are too cute and perfect to style for fall! However, according to some reviews, it's best to go a half size up when shopping.

<p><a href="https://www.amazon.com/dp/B08KHT1W2C?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Soda Pilot Chelsea Fashion Boots </p><p>$45.00</p><p>amazon.com</p><span class="copyright">Amazon</span>

Dr. Martens Leonore Fashion Boots

You won't ever have to worry about cold feet in these boots. They're lined with a warm faux fur for ultimate comfort!

<p><a href="https://www.amazon.com/dp/B01B271IK0?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Dr. Martens Leonore Fashion Boots</p><p>$158.95</p><p>amazon.com</p><span class="copyright">Amazon</span>

Steve Madden Women's Leopold Chelsea Boot

They might not be blue suede shoes but this suede Chelsea boot is timeless! This color works with a variety of outfits, so they'll look just as great in pants as they will paired with a cute skirt.

<p><a href="https://www.amazon.com/dp/B09619H6PB?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Steve Madden Women's Leopold Chelsea Boot</p><p>$99.95</p><p>amazon.com</p><span class="copyright">Amazon</span>

Brighton Ankle Boot

If you need a little extra support from your shoes, these boots have got your back! They feature extra arch support for all day comfort.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.vionicshoes.com%2Fbrighton-ankle-boot.html%3Fcolor%3D1357&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Brighton Ankle Boot</p><p>$149.95</p><p>vionicshoes.com</p><span class="copyright">Vionic</span>

Mix No. 6 Mariana Bootie

These boots are giving off major rock 'n roll vibes! They're definitely a pair that will make any wearer feel instantly cooler.

<p><a href="https://go.redirectingat.com?id=74968X1596630&url=https%3A%2F%2Fwww.dsw.com%2Fen%2Fus%2Fproduct%2Fmix-no.-6-mariana-bootie%2F532399&sref=https%3A%2F%2Fwww.thepioneerwoman.com%2Ffashion-style%2Fg37678622%2Fbest-chelsea-boots-for-women%2F" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Mix No. 6 Mariana Bootie</p><p>$34.98</p><p>dsw.com</p><span class="copyright">DSW</span>

Asgard Women's Waterproof Chelsea Boots

If you're in the market for a new pair of ankle length rain boots these would be a great pick! They are not only affordable, but are also a #1 bestseller and almost 15,000 five-star reviews.

<p><a href="https://www.amazon.com/dp/B086D4TZTK?tag=syn-yahoo-20&ascsubtag=%5Bartid%7C2164.g.37678622%5Bsrc%7Cyahoo-us" rel="nofollow noopener" target="_blank" data-ylk="slk:Shop Now;elm:context_link;itc:0;sec:content-canvas" class="link ">Shop Now</a></p><p>Asgard Women's Waterproof Chelsea Boots</p><p>$32.99</p><p>amazon.com</p><span class="copyright">Amazon</span>

You Might Also Like