Published on January 14th, 2025 | by Kirsten Borrink

Comfortable Chelsea Boots: 9 Stylish Picks for Problem Feet

At last, a recurring trend we achy-footed gals can get behind: the Chelsea boot. Credited to Queen Victoria’s shoemaker, the style is sturdy, close-fitting around the ankle, with elastic goring on the sides and a heel tab in the back. Worn as riding or “paddock” boots in the 1800s, the style gained popularity among the equestrian community, worn by men and women alike. In the 1950s, a group of young artists, film directors and socialites from the Chelsea area of west London, incorporated the boot into their “look.” The Chelsea boot soon became an icon of the Mod subculture of London making its way onto the feet of The Beatles and The Rolling Stones.

We’ve rounded up 9 comfortable chelsea boots for a variety of foot problems. Take a look!

Born Cove

Best for hallux rigidus (arthritic big toe): Born Cove

If you suffer from a painful big toe due to hallux limitus or rigidus, a thick, sturdy outsole without too much flex can help relieve the discomfort. The waterproof Born Cove features a thick rubber outsole and an embedded steel shank for stability and support. A round toe box adds to the overall comfort and a removable footbed may allow for an orthotic. Find the Born Cove in sizes 6-11 for $149.95 from Zappos, Nordstrom, and Amazon.

Best orthotic-friendly Chelsea boot: Samuel Hubbard Van Ness

This is a beautiful, Portuguese-made boot with a removable triple-density footbed and lightweight yet thick, durable outsole. Note the side zipper for ease of entry. The reviews are excellent and the price is right (currently on sale). Available in sizes 5.5-11 for $120 from Samuel Hubbard.

Best for bunions/wider forefoot: Ariat Fatbaby Twin Gore Chelsea

Zappos customer praises the Ariat Fatbaby Twin Gore:

“I have trouble finding boots with a toe box wide enough to be comfortable, but these are perfect.”

Along with a generous toe box, this cute Ariat boot has good arch support, lightweight outsole and cushioned insole. Available in sizes 5.5-11 for $109.95 from Ariat , Zappos, and Amazon.

Comfortable Chelsea Boots — Sorel Evie II

Best wedge Chelsea boot: Sorel Evie II

Do your feet just feel better in a wedge? The Sorel Evie II features a 2″ wedge heel with 1/2″ platform so it adds just a little height without compromising comfort and walkability. Waterproof leather or suede keeps the feet high and dry! Available in sizes 5-12 for $140 from Sorel.com, Zappos, and Nordstrom .

Best cork/latex footbed Chelsea: Stegmann Lieben

More of a chelsea shoe, the Stegmann Lieben is for feet that crave Birkenstock-type footbeds (cork and latex that conforms to the foot shape over time). The footbed is also removable and may accommodate an orthotic. Find a pair in sizes 6-12 (order up a half size if you’re a 9.5 or larger) for $159 from Stegmann USA.

**And just because it’s so cute and gets great reviews for comfort: Spring Step Nonia**

Ok, so it’s not made of real leather, but it has plaid inserts! Plus it’s affordable, gets great reviews for comfort and has a side zipper. Find in euro sizes 36-43 (5.5-12.5) for $78 from Zappos, Spring Step Shoes and Amazon.

Best for Big Feet: Frankie4 Crawford

Podiatrist-designed, the Frankie4 chelsea boot comes with a Sole Saver Pack® of inserts to get a good fit whether you have more narrow or wide foot. The Crawford upper is made of water resistant suede and a shock-absorbing slip-resistant sneaker outsole. Available in sizes 6-13 for $166-238 from Frankie4 and Nordstrom.

Best for bunions or feet that need extra-roomy toe box: Lems Chelsea boot

Native to Boulder, Colorado, Lems specializes in zero-drop, foot-shaped shoes and boots. Read through the positive reviews from customers with diabetes, Morton’s neuroma, bunions, wide feet…they love their new Lems. Find in sizes 6.5-11 for $150 from LemsShoes.com.

Best Chelsea for Plantar Fasciitis: Fitflop F-Mode Chelsea boot

If you’ve found plantar fasciitis relief in a pair of Fitflop sandals, you’ll love their Chelsea boots as they feature the same triple-density Microwobbleboard midsole. Think firm cushioning with support versus squishy cushioning which does no favors for the heels. Find Fitflop Chelsea boots in sizes 5-11 for $85-180 from Fitflop.com, Amazon, and Zappos.

Do you have a favorite pair of comfortable Chelsea boots? Leave us a comment and let us know!