Comfortable Chelsea Boots: 7 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 7 comfortable chelsea boots for a variety of foot problems. Take a look!

Our first comfortable chelsea boot is podiatrist-recommended. Dr. Paul Macaulay, a UK-trained podiatrist practicing in Singapore speaks highly of the Ecco Modtray chelsea boot in this video.
“If you’re suffering with plantar fasciitis or achilles tendonitis, then considering your heel height is going to be really important. We’re going to be looking for a heel height of 1.5 to 2.5 centimeters,” (Roughly a half inch to one inch) – Dr. Paul’s advice
The Ecco Modtray Chelsea features a rounded toe, soft full-grain leathers, removable insole and 1.5″ lug sole with 3/4″ platform. The other boot Dr. Paul references in the video is the Ecco Nouvelle style available through Amazon.
• Sizes: Euro 35-42 (4-11) • Width: M • Price: $97-225 from Ecco US, Zappos & Amazon

“Fantastic boot! Super comfortable, love the rounded toe, lots of room for my bunion.” – Ariat customer
“I have a huge bunion but these boots are still so comfortable to wear all day.” – Ariat customer

Give the toes some room! The Ariat Fatbaby Chelsea boot features a wide, rounded toe box–perfect for bunioned feet. Add Ariat’s 4LR™ technology and you’ve got yourself a lightweight yet supportive chelsea boot that’s on trend for concert-going, market-shopping, classroom-teaching and yes, barn chores too. We love all the fun color and pattern combos available (but they do come in neutrals too).
• Sizes: 5/5-12 • Widths: M & W (certain sizes and colors) • Price: $87.99-119 from Ariat, Zappos & Amazon

I gasped when I saw the colors these come in. Dramatic? Perhaps. But wait until YOU see the bottle green ones. Keep the tootsies toasty this winter in the Rieker Amalia 65 with its faux suede upper and warm faux fur lining. A padded footbed (non-removable) cushions the soles while a shock-absorbing lug sole provides good traction.
• Sizes: Euro 36-42 (5.5-10.5) • Width: M • Price: $120-135 from Rieker US, Zappos, Nordstrom & Comfort One Shoes

Oh my gosh, these booties are perfect. I’ve been on the search for a dressier, but comfy, bootie for over a year. The toe box is just wide enough, there’s just enough arch support, and the bootie itself is so lightweight I hardly feel them. – Stegmann customer
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. The goring hits below the ankle bone so no worries about it rubbing.
• Sizes: 6-12 • Width: M • Price: $164 from Stegmann USA

“These may be the most comfortable boots I’ve ever owned! The cushioned support is amazing and feels so good on my arches. I work in retail and I’m able to stand in these for hours with minimal back pain. They look great with my bootcut and wide leg jeans, as well as skirts and dresses. True to size.”- Elizabeth, Frankie4 customer

Can a Chelsea boot be both sleek and supportive at the same time? Minimalistic with maximum foot support? Elegant yet durable? Yes, yes and yes. Welcome the podiatrist-designed Frankie4 Liberty boot with a Sole Hero® Footbed (layered footbed with heel, arch and forefoot support). Need more room in the toe box? Take out the full length footbed and insert the half length insert included in the Sole Saver Pack®! Find out more about the Frankie4 brand in my video review here .
• Sizes: 6-13 • Width: M • Price: $278 from Frankie4

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 wide toe box chelsea boots. If you’re not into the barefoot feel and need more arch support, just add your favorite to the Lems Chelsea boot and voila! you’re good to go.
• Sizes: 6-12 • Width: one width in Lems WIDEST Natural-Shape Fit • Price: $165 from Lems Shoes

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!
Pleeeze review some Wide width shoes and boots.