The 11 Best Travel Friendly Boots for Fall

The 11 Best Travel Friendly Boots for Fall

Even the most experienced travelers find fall packing a challenge. Will there be randomly hot days followed by cold, rainy nights, or cold mornings replaced by warm, windy afternoons? A good traveler should always be prepared. After all, nothing gets in the way of walking around a new city like cold, wet feet. Here are eleven boots that are perfect for fall weather.

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Rothy’s The Chelsea


Chelseas is Rothy’s cult-favorite travel shoe brand that was the first to enter the boot category. These stylish boots are made from used water bottles, making them extremely lightweight, durable and machine washable. Rear pull tabs make it easy to slide out of airport security.

Baffin Package Rain Boot

Yellow single rain boots (left) and the bottom sole of those rain boots (right)

You don’t want to be stranded without rain boots if you’re going somewhere with wet weather, but these shoes certainly take up a lot of luggage space. Unlike most, these boots by Baffin take up almost no space as they can be rolled up and neatly stowed into the included carry case. The brand beats similar, cheaper styles thanks to a removable insole that makes it comfortable for long walks.

FrancoSarto Happily Bootie

Two looks of FrancoSarto Happily Bootie in red-brown

The Happily Bootie from FrancoSarto is a must-have boot for any city getaway this fall. The classic leather style will pair with any outfit, while the shock-absorbing sole makes it comfortable to walk all day and all night.

Vionic Bowery Chase Chukka Boot

Two color options, black, and brown, from Vionic Bowery Chase Chukka Boot

The Bowery Chase Chukka boot from Vionic will complete your travel wardrobe this fall. The leather upper goes well with jeans or a business look, while the weather-resistant upper protects you from rain or snow. You’ll walk in confidence knowing they’ve received the American Podiatric Medical Association’s Seal of Acceptance.

Travel Collection Pocket Boots

The Journee Collection Pocket Boot, unzipped (left) and the Journee Collection Pocket Boot, zipped (right)

Who needs a wallet when you have the Journee Collection Pocket Boot? These knee-high boots have hidden pockets inside that can hold your smartphone, cash and credit cards, offering you easy access—but not pickpockets.

Arcopedico L31D . High Riding Shoes

Arcopedico L31D Tall Riding Boots in brown (left) and Arcopedico L31D Tall Riding Boots in black (right)

Don’t overload your trunk with bulky boots—the Arcopedico L31D Riding Weight only weighs nine ounces. Even better? They are machine washable, so you can put them in the washing machine after each trip. Between washes, the “Sansmell” deodorizing system is anti-microbial to keep your feet fresh.

White Mountain Dear Bootie

Two views of White Mountain Dear Bootie in light brown

Add a bit of painless height in White Mountain’s Dear Bootie. The small, stable platform heel gives you a bit of lift to enhance your look. They stretch at the ankles for ease on and off and can be dressed up or down for multiple occasions.

Trotters Misty Riding Boot

A pair of Trotters Misty Riding Boot, one facing forward and one facing back (left) and one boot of the pair facing sideways (right)

Riding boots are on trend for fall, and nothing fits the bill quite like the Trotters Misty Riding Boot. These boots feature a cushioned footbed, breathable lining and stretch panels in addition to side zips for an optimal fit. The 1-inch heel adds height gain without getting out of hand and the leather upper enhances on-the-go wear.

Chelsea Boots Legacy Red Wing

Two looks a pair of Red Wing Heritage Chelsea Boot in dark blue
Red Wing Shoes

Booties have become a fall style staple in recent years, and they’re perfect for traveling; they offer more warmth than flat boots but are easier to pack than tall boots. The Chelsea Red Wing Heritage Boot has a clean, classic design that will look great with any outfit. The leather loop on the back makes it easy to pull on and take off. These boots are ready for wet weather, thanks to an outsole with goodyear welt and Vibram mini-lugs to keep your feet stable. Made from premium Red Wing Heritage leather, Chelsea boots will shape your foot as you wear them, creating a perfect fit.

Rockport Waterproof Storm Surge Toe Boot

Two-look Rockport Waterproof Storm Surge Toe Boot in black

If the weather forecast calls for wet weather, bring along Rockport Storm Surge boots, which are small enough not to dominate a carry-on bag and comfortable enough to wear on a plane. These boots are made using the trademarked Hydro-Shield Waterproof process, which uses sealing seams, a water-resistant sole, and a waterproof outer to keep you dry.

DailyShoes Pocket Shoes

DailyShoes Pocket Boots light brown with unzipped storage pocket, showing money and credit card inside (left) and same boot facing forward (right)

Pack these boots by DailyShoes and it’s wallet-free, thanks to the built-in secret purse pocket. This little zippered pocket can store cash, credit cards, keys and more. Plus, these comfortable walking boots come in colors to match any outfit.

Caroline Morse Teel believes a great pair of fall boots can make or break a trip. Follow her fashionable adventures on Instagram @travelwithcaroline.

Some product reviews are sent to us free of charge and with no incentive to offer favorable reviews. We offer our unbiased, positive and negative opinions, and will never accept compensation for reviewing a product.

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We handpick everything we recommend and select items through testing and reviews. Some products are sent to us for free with no incentive to offer favorable reviews. We offer our unbiased opinion and do not accept compensation for reviewing products. All items are in stock and prices are accurate at the time of publication. If you buy something through our link, we may earn a commission.

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