It’s time to give uncomfortable shoes the boot. As the weather cools and the sandals go to the back of the closet, you’ll want to grab a pair of fall kicks that are nice to look at and nice to wear. If you’re feeling overwhelmed by the options, we’ve got your back. We spoke to our favorite foot and shoe experts about their recommendations for the best brands and styles of casual and dress boots to go for.
“When looking for a fall boot, check that the boot is not too narrow at the heel or at the toes, which will prevent your toes from having room to maintain their regular position needed for function,” Dr. Adenike Sonaike, a podiatrist with Baker Street Health In Motion in Fair Lawn, New Jersey, told HuffPost. “A boot with a flimsy material can cause ankle instability. A boot made of leather can provide support and mold to your foot shape over time making them comfortable to wear.”
According to Sonaike, while they may be in style this season, pointy-toed shoes can lead to arthritic joints, bunions and painful calluses. Furthermore, if you know you have weak ankles or a history of ankle sprains or injuries, Sonaike says you should avoid any styles described as “glove” or “sock” boots. Lastly, if you’re seeking a boot with a little height, “stretching should be part of your regular routine because your Achilles tendon will get accustomed to functioning at a shorter length,” Sonaike said, recommending toe touches to “help elongate the tendon to prevent Achilles tendinitis.”
Michael Fishkin, a certified pedorthist at Northern Illinois Foot & Ankle Specialists, says to really take a look at the shape of your feet and to try to look for shoes that match you. “You want to make sure that with any shoe that has a pointed/almond-shaped toe, your toes are not in the narrowest part of the boot,” Fishkin told HuffPost. “A full thumbnail of space from the end of the footwear to the longest toe is ideal.”
Of course, while both experts express that trying on shoes in person is ideal, they understand that buying online is often more convenient and can give you more options. Sonaike and Fishkin recommend looking into a store’s return and shopping policies and ordering shoes in two different sizes (often your usual size and a half size larger) to see what fits best. “Pay close attention to the side profile of the shoe,” Sonaike said. “The side profile (the side with the medial arch) can provide details such as the heel height, sole thickness and arch shape/support of the shoe you wish to purchase.”
To get you on the right foot, Sonaike and Fishkin break down their favorite brands and styles of fall dress boots.
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Frye
When it comes to casual and dressy fall boots, Fishkin really likes Frye. "Frye boots focus on craftsmanship," he said. "They are one of the sturdiest styles of shoes because they use something called a ‘Goodyear welt.' This provides additional durability and water protection as the layers of leather are stitched together."
A Goodyear welted shoe is made with an embedded cork footbed that's breathable and shapeable to your foot and has a metal shank at the heel to maintain the shoe's shape. "Cork is porous and malleable, and with time will conform to the shape of the wearer’s foot for a customized fit," Fishkin said.
The bulk of Frye's styles are made with high-quality leather and this celebrated Goodyear welt, meaning your shoes will feel good to wear and last a long time. While the site offers a lot of great styles, I love the men's work-boot-style lace-ups and these super adorable retro-style ankle Campus boots.
Vagabond
After years of asking strangers what boots they were wearing and hearing them say "Vagabond," I finally got a pair of Vagabond platforms. Imagine my excitement when Sonaike recommended the brand for well-made everyday boots that give comfort and support. Pictured here are a men's lace-up pair and a super chic set of platforms, though, truly, everything this Swedish brand makes is great-looking and so versatile.
Crafted from high-quality leather, they're not a bargain item, but they feel great on the feet right out of the box. I have a wider foot and find myself going up a half size. (Sometimes their product descriptions will recommend going up a whole size.) I can attest after break-in that they are very comfortable, and all the kind strangers I've ever asked have said the same. A few weeks ago, a girl in a bar had me try on her Vagabond boots because she was so passionate about how comfy they are, and it really sealed the deal for me.
Dr. Martens
Growing up in the punk scene, I couldn't wait to get my first pair of Dr. Martens. In a recent conversation with my dad (an orthotist/prosthetist) and my favorite aunt (a retired physical therapist), both said they recommend the British boots for their supportive sole and arch support. Sonaike also recommends Dr. Martens for daily wear, noting their support. While there are certainly some styles of Dr. Martens reminiscent of the band Kiss, there are a bunch of more low-key, mature-leaning options like these unisex Chelsea boots.
Blondo
Per Fishkin, "Blondo boots are great. They use durable leather and their boots come with a waterproof coating. They're easy to slip on and wearers say they are comfortable." Another brand offering comfort and quality while still giving you style, Blondo has waterproof offerings that are perfect for fall and in-between seasons. How cute are these women's pull-on ankle boots with a cushioned insole and textured grippy outsole?
Clarks
It's no surprise that Clarks, a HuffPost readers' favorite brand, comes recommended by Sonaike as another comfortable and supportive everyday option. The brand is known for its timeless styles, like these tan desert boots in men's sizes. Still, in recent years, it's also come out with a bunch of different, modern options, like these braided motorcycle-style kicks in women's sizes that feel a little funky while still being easy to style.
Rockport Caspe boots
Another specific suggestion from Fishkin is the men's Rockport Caspe lace-up boots. "These shoes are made with genuine leather that [is] water-resistant. The rubber outsole is slip-resistant. They feature a removable insert that can be replaced with an orthotic or additional arch support," he said.
Everlane
You may already know Everlane for its elevated minimalist clothing and the company's environmental initiatives. Yet, Sonaike says, "Everlane boots are a great option and they do not compromise function over fashion." The brand currently offers only women's boots, in a variety of styles ranging from more casual to more dressy and even knee-high options. I love these square-toe ankle boots, which look easy enough to throw on with jeans but nice enough to wear to work.
Sam Edelman Laguna boots
For a brand and style, Fishkin also likes the Laguna boots from Sam Edelman. "These are stylish and sturdy. They have a lugged outsole for increased traction and structure," he said. Coming in a bunch of colors, these women's chunky Chelsea boots give your toes room without looking super bulky.
Ariat
I have written before about my love for Ariat boots and was overjoyed to hear Fishkin recommend the brand too. "Most styles from Ariat are quality-made," he said. "They have a durable outsole for enhanced traction and structure. They have a specially designed shank through the midsole for ergonomic support. They [often] come in medium and wide widths for a better fit." Created as an equestrian athletic shoe brand, Ariat offers horse-riding shoes and general Western cowboy boot styles. Still, the brand offers everyday casual and dress boots like these men's round-toe pull-ons or these women's waterproof Chelsea boots.