W+G Editor-Beloved Boots Underneath $200

Sizes: 6.5-11 | Colors: 2 | Materials: not specified

Soul Naturalizer’s knee-high boots lend itself well to long dresses and midi skirts as it does to a sweater and jeans, leaving little to no room for error as you dress for office hours or a night out. Available in crowd-pleasing neutrals, the pair hasa circumference of 14.57 inches, and stretchy gore panels to offer wider calves some wiggle room as well. Plus, the zippered side makes it as easy to put on and take off. The pair also has a low 2.6-inch wedge heel, along with a slightly lugged outsole to keep you steady on your feet and comfortable for extended periods of wear.

Sizes: 5-14 | Colors: 3 | Materials: leather

My pair of lug-sole Chelsea boots from Sam Edelman are comfortable, supportive, and—just as importantly—durable. It’s been scuffed and soiled, but it’s as solid as the day I bought it several years ago. The boots have all the features of a classic Chelsea-style shoe (like elastic gore paneling and an almond-shaped toe), plus a 1.5-inch heel that offers just enough height. The pair also has a lugged outsole that provides me with security when the weather takes a turn for the worst (I’ve worn it to walk on icy streets without so much as a worry of slipping or sliding). What’s more, it comes in medium and wide widths—and with leather or suede uppers. I opted for the leather version, which, in my opinion, offers an ideal balance of style and functionality.

Sizes: 5-12 | Colors: 6 | Materials: leather

When it comes to boots, this pair is a fall-friendly staple for Well+Good Health Director Kaitlin Ahern. Ahern says, “They’re a fun twist on the classic Chelsea-style boot with a chunky heel and matte finish, so they’re buttoned-up with just a little bit of edge.” Not only are they stylish, they are also comfortable to wear: “The leather is super-soft, and despite the heel, they’re actually comfy to walk in,” she says. Plus, you can select from six different colors to match your style.

Sizes: 5-12 | Colors: 16 | Materials: rubber

Fall weather can be unpredictable—and when it rains, a great pair of rain boots can save the day. The Merry People Bobbi boots are beloved by both me and Well+Good Commerce Editor Francesca Krempa. Krempa previously said, “They’re so cute and come in a literal rainbow of colors that make dressing for gray rainy days much more fun.” They are 100 percent waterproof, too: “I’ve worn them in all four seasons at this point, in everything from humid summer thunderstorms to winter ice and sleet, and [I] can honestly say they’ve kept my feet dry, happy, and cute in all sorts of weather.”

Pros:

100 percent waterproof

Wide toe box

Cons:

It isn’t as versatile compared to other options on the list

Sizes: 5-13 | Colors: 8 | Materials: suede

It’s no secret that Well+Good editors have a huge crush on Cariuma shoes, including the Oca Therma Suede Boot. “These are a home run for comfort and functionality,” Well+Good Social Producer (and former Senior Commerce Writer) Taylor Bell previously said. “For one, they’re not bulky at all. In fact, they have the same lightness of a sneaker so your foot doesn’t feel weighed down as you walk. Plus, I didn’t even have to wear socks with them to keep my feet warm. The shearling fabric feels so soft against your skin, and [it] naturally packs in heat.” It’s versatile, too: “They pair nicely with the majority of my winter wardrobe, which includes leggings, high-waisted jeans, and warm tops galore,” she wrote.

Normally $180

Sizes: 5-11 | Colors: 1 | Materials: suede

FitFlop’s flatform Chelsea boots areas comfy as a pair of sneakers, but offer you over one inch of additional height—something to which Well+Good contributing writer Rebecca Norris has previously confirmed. “From a comfort stance, they far surpass any other Chelsea boots I’ve worn, thanks to their lightweight feel and expertly designed Microwobbleboard technology,” she wrote. “In layman’s terms, the footbed and midsole [are] outfitted with three layers of targeted cushioning.” Norris adds that the pair has “modern sneaker flair that can easily be dressed up or down.” All to say: “If you’re looking for a new versatile and convenient boot silhouette to add to your closet, these boots fit the bill,” she proclaimed.

Sizes: 5-11 | Colors: 7 | Materials: Gore-Tex

If you want to enjoy some spectacular fall hiking, consider a pair of hiking boots like this option from Hoka. It’s beloved by outdoor enthusiasts, including Well+Good contributing writer Megan McCarty. According to McCarty in a previous review, the Anacapa 2 has “loads of cushion, a rocker-like bottom that propels you forward, serious stability, and no painful break-in period.” What’s more, the Vibram outsole provides great traction on all terrains. The hiking boot also comes with the Seal of Acceptance from the American Podiatric Medical Association (APMA), which ensures you of its comfortable support. Shop it in seven colors ranging from understated to fun and flashy hues.

Normally $250

Sizes: 10-12 | Colors: 2 | Materials: not specified

When winter inevitably rolls around, a pair of warm—and waterproof!—Uggs are a staple for Well+Good Fitness Editor Danielle Zickl. “I got these boots last year because I’d moved to a walkable city and realized I didn’t actually have a pair of real winter boots. In addition to a boot that was waterproof and would keep my feet warm, I still wanted something stylish and that would look good with any type of outfit,” says Zickl. “The Ugg Maxi Mini Boot fit the bill. I’ve been waiting for winter to come around because I’m so excited to wear them again this year!” If these boots are sold out, consider the Ugg Classic Klamath Mini. It’s a similarly warm and waterproof boot, only it comes with a higher price tag than the Maxi Mini.