Even the most seasoned travelers find fall packing to be a challenge. Will there be a random hot day followed by a cold and rainy evening, or a frosty morning that gives way to a warm, breezy afternoon? A good traveler should always be prepared. After all, nothing puts a damper on walking around a new city like cold, wet feet. Here are eleven boots that are perfect for fall weather, plus are packed with travel-friendly features like secret pockets and sneaker technology.
Rothy’s The Chelsea
The Chelseas are cult-favorite travel shoe brand Rothy’s first foray into the boots category. These stylish booties are made from repurposed water bottles, making them ultra-lightweight, sustainable, and machine washable. A back pull tab makes these easy to slide out of at airport security.
Baffin Packables Rain Boot
You don’t want to be stranded without rain boots if you’re headed somewhere with wet weather, but they sure do take up a lot of luggage room. Unlike most, these boots by Baffin take up almost no space because they roll up and store neatly into an included carry pouch. This brand beats out similar, cheaper styles thanks to the removable insole that makes them comfortable for long walks.
FrancoSarto Happily Bootie
FrancoSarto’s Happily Bootie are the must-have boots for any city breaks this fall. The classic leather style will pair with any outfit, while a shock-absorbing sole makes these comfortable to walk all day and all night in.
Vionic Bowery Chase Chukka Boot
Vionic’s Bowery Chase Chukka boot will complete your travel wardrobe this fall. The leather upper works with jeans or a business look, while the weather-resistant upper protects you from rain or snow. You’ll walk confidently in these knowing that they’ve received the American Podiatric Medical Association’s Seal of Acceptance.
Journee Collection Pocket Boot
Who needs a purse when you’ve got the Journee Collection Pocket Boot? These over-the-knee boots have a hidden pocket inside that can hold your smartphone, cash, and credit cards, offering easy access for you—but not pickpockets.
Arcopedico L31D Tall Riding Boots
Don’t weigh down your luggage with bulky boots—the Arcopedico L31D Riding Boots weigh just nine ounces. Even better? They’re machine washable, so you can just toss them in the washer after every trip. In between washes, the “Sansmell” deodorizing system is anti-microbial to keep your feet smelling fresh.
White Mountain Dalby Suede Bootie
Add a bit of height without the pain in White Mountain’s Dalby Suede Bootie. The stable, small stacked heel gives you a little lift to elevate your look. The almond-shaped toe and plush suede upper make these booties extra comfortable.
Aetrex Chelsea Riding Boot
Riding boots are on-trend for fall, but cheaper pairs can be flimsy and unsupportive with no arch support. Not so with the Aetrex Chelsea Riding Boot, which features the “Aetrex Healthy Three” of arch support, memory foam cushioning, and anti-microbial technology. This trio will keep your foot properly aligned, unfatigued, and bacteria-free.
Red Wing Heritage Chelsea Boot
Booties have become a fall style staple in the last few years, and they’re perfect for travel; they offer more warmth than flats but are easier to pack than tall boots. Red Wing Heritage’s Chelsea Boot has a classic and clean design that will look good with any outfit. A leather loop in the back makes these easy to pull on and off. These boots are ready for wet weather, thanks to an outsole with a Goodyear welt and Vibram mini-lug to keep you steady on your feet. Made from Red Wing Heritage’s signature premium leather, the Chelsea boots will mold to your feet as you wear them, making a custom fit.
Rockport Waterproof Storm Surge Toe Boot
If the forecast calls for wet weather, pack Rockport’s Storm Surge boots, which are small enough not to dominate a carry-on and comfortable enough to wear on the plane. These boots are constructed using a trademarked Hydro-Shield Waterproof process, which uses seam-sealing, waterproof insoles, and a waterproof outer to keep you completely dry.
DailyShoes Pocket Boots
Pack these boots by DailyShoes and go purse-free, thanks to the secret wallet pocket that’s built in. This small zippered pouch can hold your cash, credit card, keys, and more. Plus, these comfortable walking boots come in colors to match any outfit.
More from SmarterTravel:
Caroline Morse Teel believes a good pair of fall boots can make or break a trip. Follow her fashionable adventures on Instagram @travelwithcaroline.
Some review products are sent to us free of charge and with no incentive to offer a favorable review. We offer our unbiased opinions, positive and negative, and will never accept compensation to review a product.
We hand-pick everything we recommend and select items through testing and reviews. Some products are sent to us free of charge with no incentive to offer a favorable review. We offer our unbiased opinions and do not accept compensation to review products. All items are in stock and prices are accurate at the time of publication. If you buy something through our links, we may earn a commission.