The Best Boots for Fall and Winter

Your sandals’ days are long gone, and it’s time to take inventory of your fall boot collection. If you’re in a place where a few inches of snow is just an average Tuesday, you might want to invest in seriously awesome weather-proofed boots — if you don’t already have a few pairs on hand. But if not, you can prioritize style and function as well. Here’s what to try this season as new fall boots hit shelves or your online cart.

_{Prices are accurate as of October 30, 2025. Subject to change.}

Best Handcrafted Boots: Duckfeet Århus

Duckfeet’s Arhus boots are an investment, but a worthwhile one. Handcrafted in Europe, these are made with terracare leather and 100% sheep’s wool lining. Because the sole is replaceable, they’ll outlast storms and fashion cycles. They’re constructed to allow feet to breathe and tend to follow the natural shape of the foot, making them truly comfortable (and warm) boots for fall and winter activities. I found them a bit stiff to begin with, but once you break them in you won’t take them off until spring.

Best Ankle Boots: Aetrex Mila

Sometimes boots get a bad rap for aggravating foot pain, but that isn’t the case with the Aetrex Mila. These weatherproof, low-style leather boots have a side zipper for easy on and off and each Aetrex shoe includes the brand’s custom orthotic system to help relieve plantar fasciitis and heel or arch pain. The removable insole makes customization possible, ensuring you’re getting top comfort for your foot. I have a high arch, so I appreciate that I can use my own inserts to maximize comfort and support to reduce foot, leg, and back pain.

Best Chelsea Boots: Thursday Boot Co. Duchess

These everyday boots will catch everyone’s eye. With a classic styling, leather upper, and elastic goring, the Duchess is perfect for slipping on while running errands or dressing up for a date night. They’re comfortable right out of the box, and made with a shock-absorbing insole, so they’ll only continue to get more comfortable with time.

Best Work Boots for Men: Wolverine DuraShocks SR Icon

Wolverine’s DuraShocks SR Icons are great men’s boots that power through the toughest environments while maintaining comfort and durability. They’re made with DuraShocks cushioning to absorb shock and provide lasting comfort, no matter what the work task is. They also come in medium and extra-wide up to a size 14, so no hard-working person has to give up comfort in the name of fit.

Best Hiking Boots: Hoka Transport Chukka GTX

If your fall activities involve hiking or exploring the outdoors, don’t overlook Hoka’s Transport Chukkas. Hoka is known for its comfortable tennis and athletic shoes, and these hiking boots are no exception. They’re waterproof and provide both protective and responsive cushioning, giving you the best level of comfort — no matter your speed or environment. Hoka also focused on sustainability with these shoes, using recycled polyester, recycled Vibram rubber, and a soy-based sockliner.

Best Platform Boots: Teva ReEmber Mid Platform

Fall weather can be unpredictable, but the Teva ReEmber Mid Platform boots will have you prepared for whatever weather comes your way. With platform midsoles, these boots cushion your foot for comfortable all-day wear. The protective coating causes water to bead right off, keeping your feet dry and warm. They’re also treated with a natural anti-odor treatment to help keep odors at bay.

Best Tall Boots: Naturalizer Rena 2

Naturalizer has a reputation for comfort that’s been years in the making, and the Rena boots live up to that tradition. Naturalizer’s Contour+ Comfort technology provides a great fit and comfort all day long and the 1-inch block heel gives just enough height while still providing walkability. The removable insole allows for customization and the leather upper makes these a go-to for comfort and style.

Best Boots for Warmth: Mou Eskimo 24

When really cold weather hits, you don’t want to sacrifice comfort for warmth. The Mou Eskimo 24 boots give you the best of both worlds. Made with sheepskin and wool stitching, paired with a supportive heel and rubber sole, these boots keep you comfortable no matter how cold the thermometer reads. They’re a splurge, but they make a great gift for your holiday list, especially in a wild, out-of-the-box color.

Feature Image Credit: encierro/ Shutterstock