10 Comfortable Tall Boots for Women 2025

Are you a fan of tall boots? I had a pair of taupe Naturalizer knee-high boots from 2012 that I finally parted with due to a faulty zipper, but I loved those boots. I wore them with skinny jeans (I know, I know, it’s all about the wide legs these days), skirts and dresses–the fit was perfect and they kept my legs warm and put the “dress” in dress casual. It’s nice to see knee-high boots back for winter 2024-2025! I’ve rounded up ten comfortable tall boots with a good fit and support.

“Love! These are so great! It is tough to find a boot to fit my slim calves.” – Zappos customer Jo

Aren’t these beauties? If your calf circumference is under 15″, the Sofft Sharnell II is a great boot to try. Stain-resistant, waterproof Italian leathers make up the upper and shaft keeping your feet dry while a cushioned footbed and arch provide all-day comfort.

• Sizes: 6-11 • Width: M • Calf circumference: 13″ adjusting to 15″: • Price: $186-249 from Zappos, Amazon (find a deal on eBay)

Sometimes a low wedge feels better on aching feet than a typical flat or block heel and the Aerosoles Binocular is an affordable option! The faux suede upper has a little stretch to it and the shearling trim is just around the top of the boot.

• Sizes: 5-12 • Width: M & W • Calf circumference: 16″ • Price: $89-149 from Aerosoles, Amazon & Zappos

“Super cute. Beautiful leather, great style to wear with dresses, jeans and skirts. Classic and will last for years! I wear 7, ordered a 7 1/2 to allow for orthotics. Slightly narrow but fit great if I wear thinner socks. Very happy!!!” – Nordstrom customer

Are the beautiful Frye Campus boots out of your budget? Mine too. The Dingo Vagabond is high quality dupe for less than half the price of the Fryes. Customer reviews are mostly positive for good fit and feel (keep in mind this is a pull-on style–no zipper).

• Sizes: 6-11 • Width: M • Calf circumference: 12″ • Price: $169.95 from Dingo 1969, Nordstrom, Amazon, Zappos

What sets this lovely tall boot apart is Abeo’s BIOsystem® orthotic footbed, designed to support your arches, cushion your heels, and keep your body aligned. The deep heel cup absorbs shock, while the roomy toe box takes pressure off the bunions. Whether you deal with plantar fasciitis, metatarsalgia, or just tired feet, these boots are built to help relieve pain and fatigue while staying stylish.

• Sizes: 5-11 • Width: M • Footbed style: regular support & metatarsal support • Price: $279.95 from Nordstrom, Amazon & The Walking Company

“Oh my goodness, this boot is amazing! Love the soft look and spacious toe box. Perfect for dresses and skirts. Wore it all day right out of the box.” Miz Mooz customer, Carmelita

It’s all in the details. Portuguese-made Miz Mooz Lisbon kicks the regular riding boot up a notch in the Lisbon boot with its slightly slouched design with ruching and supple leather upper in rich hues. A padded footbed and low one-inch heel add to its all-day comfort.

• Sizes: 6-11 • Width: M • Calf Circumference: regular – 15″ & wide – 16″ • Price: $249.95 from Miz Mooz, Nordstrom & Amazon (regular calf only)

Real leather boots are typically priced over $150 but I found a beautiful pair for under $140! The Clarks Adalynn Hope tall boot features a densely padded footbed with extra cushioning at the heel and ball of foot, a round toe and a rubber lug sole for stability.

• Sizes: 5-12 • Width: M & W (this is foot width, not calf width) • Calf circumference: 14 1/8″ • Price: $129-139.99 from Clarks & Amazon

If you can handle a 2.5″ heel, this lovely leather tall boot designed by Nordstrom might be in your future, especially when you see the price. The Hanna boot is a crowd-pleaser with a 4.5 out of 5 star average for fit, feel and style.

• Sizes: 5-12 • Width: M • Calf circumference: regular – 14″ & wide – 16″ • Price: $89 from Nordstrom