Comfortable Chelsea Boots: 7 Stylish Picks for Problem Feet

At last, a recurring trend we achy-footed gals can get behind: comfortable Chelsea boots.  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.

But which Chelsea Boots are best for problem feet?  We’ve rounded up 7 of the best with supportive footbeds, rounded toe boxes and other comfort features…

“I recommend Aetrex products to my patients because it helps provide the right balance and support to relieve and prevent foot conditions like Plantar Fasciitis. Unlike other brands; the contour, position and height of the Aetrex product arch support aligns anatomically in the proper place to help support our bodies from the ground up.” – Janine Taddeo, DPM

The APMA (American Podiatric Medical Association)-approved, the Aetrex Kaylee not only features all the good-for-you comfort features, it’s just so cute with its plaid goring! The removable insole is removable so you can wear it with your custom orthotic (if needed). Reviews are coming in strong for comfort and fit. Aetrex uses their patented Cobra Orthotic Insole in the Kaylee boot: see its features here.

• Sizes: 6-12 • Width: M • Price: $165 from Aetrex (30 day wear test) & Zappos

“I am loving these boots! Have not taken them off since receiving them. They’re comfortable and I can insert my orthotics for extra long wearing time. Just get them, you’ll be so happy you did.” – Ariat customer

Give the toes some room! The durable 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 & Amazon

“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: $139-164 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: $139-278 from Frankie4 & Nordstrom

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. If you’re not quite a barefoot footwear girlie, add a pair of Bridge soles for extra support.

• Sizes: 6-12 • Width: one width in Lems WIDEST Natural-Shape Fit • Price: $165 from Lems Shoes

Duckfeet footwear is handcrafted in Europe utilizing responsibly manufactured terracare® leather. A foot-shaped toe box accommodates a wider and higher forefoot due to genetics, bunions, hammertoes (hence the name “Duckfeet”).

“Duckfeet have a neutral leather footbed without any inherent arch support. Because it’s leather, the footbed will form to the wearer’s footprint over time. If support is desired, the footbed is great for accommodating most insoles as there is no built in support to compete with an insert/insole.” Duckfeet website

You can add a Duckfeet cork or wool insole to the Roskilde boot for a little more support or warmth.

• Sizes: Mens and Womens Euro 35-48 (5-14) • Width: one width that fits medium to wide feet • Price: $268 from Duckfeet USA. Use code BARKINGDOG for 10% off your purchase.

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