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Packing footwear for fall and winter travel is easy—when you have the right pair of comfortable boots. No matter if you’re a city wanderer and need a walkable boot that can dress up and down, or you’re expecting to get a little mud on the soles, Rockport is the go-to for travel boots. We’ve pulled the best-of-the-best of this season’s must-have men’s and women’s boots that look just as good as they feel. (Hint: get a head start on your holiday shopping.)
Try Them On! All boots featured qualify for free standard shipping.
The Dancer
The Boot: Cobb Hill Oliana Bootie
The Destination: Nashville
Made for fall, spring, and mild winters the Cobb Hill Oliana Bootie is casual enough for all-day wear, but with zippers, embossed panels, and a low heel, it’s dressed up enough for a long night out. The combination makes it perfect for stomping around Music City between the Country Music Hall of Fame, venues like the Station Inn, and honky-tonks, like Layla’s. Don’t be surprised if you wake up with them still on your feet.
The Après-Skiier
The Boot: Centry Panel Toe Boot
The Destination: Estes Park, Colorado
As the ideal basecamp for ventures into Rocky Mountain National Park, Estes Park is the place for back-country Nordic skiing, snowshoeing, and ice skating. But after a day of outdoor adventures, there’s nothing like a hot drink and comfortable, warm shoes. An update on the classic field boot, the Centry Panel Toe Boot is constructed with waterproof materials, making these boots resistant to water absorption—and ideal for walking on slushy streets to the Wheel Bar. It’s also cushioned throughout, a must for tired feet.
For a similar boot with rounder toe, check out the Centry Plain Toe Boot.
The Desert Wanderer
The Boot: Cobb Hill Natashya Bootie
The Destination: Palm Springs
The desert cools down in the winter—just enough so you can wear your autumn boots into winter and spring. Available in several shades in suede, nubuck, and leather, the Cobb Hill Natashya Bootie is ideal for dry climates like Palm Springs. The stacked block heel is walkable enough to head from the art museum to Ruddy’s General Store Museum, and dressed-up enough so you don’t have to change before having a pre-dinner cocktail at Bootlegger Tiki.
The Woods Walker
The Boot: Essential Details II Chukka
The Destination: Berkshires
Your motto: there’s no such thing as bad weather, just bad footwear choices. The Essential Details II Chukka is waterproof, shock absorbing, and cushioned, making this one of the best walking boots—and a smart packing choice. Take them from Beartown State Forest and Butler Sculpture Park to downtown Stockbridge; these shoes have the business vibe that allows them to play double-duty in a destination where you’re just as likely to pack jeans as trousers.
The Urban Explorer
The Boot: Cobb Hill Bethany
The Destination: New York City
When you’re discovering a new city for the first time, the last thing you want to deal with is tired feet. And, if you’re the type of traveler that likes to blend in with your environment, you also want to avoid wearing sneakers. The Cobb Hill Bethany is the answer to walk-for-miles-while-looking-stylish challenge. Its arch support, grippy sole, and comfortable footbed make this boot perfect for pounding pavement and standing during the Rockefeller tree lighting ceremony, while its vintage military-inspired look keep it stylish enough so you don’t have to change for snacks and drinks at The Wayland.
The Frequent Flier
The Boot: DresSports Modern Chelsea
The Destination: Office to Airport
When you’re in and out of airports all the time, you know how to add comfort to your ready-for-the-office look. You also know how to maximize your efficiency through security. With its slip-on, slip-off styling, and a cushioned footbed the DresSports Modern Chelsea boot is a traveler’s dream shoe. TSA checks are a breeze, and wheeling your carry-on to your gate—even if it’s at the farthest end of the terminal—is a non-issue.
The Outdoor Adventurer
The Boot: Caroline Waterproof Boot
The Destination: Jackson, Wyoming
A waterproof boot is essential if you’re traveling to destinations that get rain and snow. And for much of the U.S., the winter and holiday months bring damp weather from coast to coast. While the Caroline Waterproof Boot fits in any urban local, it also has motorcycle-styling edge you need to fit in an Old West town like Jackson. You’ll find these boots wear just as well for a night on the town at The Rose as they do a snowmobile ride through Yellowstone National Park.
The Relaxer
The Boot: Wynstin Chukka
The Destination: New Orleans
The Wynstin Chukka is the go-to shoe for everyday wear. Its subtle wingtips and foot-friendly shock absorption give it a comfortable vintage feel that help you kick back just as easily on the dance floors of The Maison and the Spotted Cat Music Club as on the paths through Audubon Park. When you’re not traveling, these boots blend in at the office and keep your feet tension-free.
The All Nighter
The Boot: Cobb Hill Rashel Buckle Bootie
The Destination: Chicago
At home in any urban environment, the Cobb Hill Rashel Buckle Bootie is the perfect shoe for ringing in 2018. It’s particularly fit for a destination like Chicago where you need the option to conceal a pair of socks while watching the fireworks over Lake Michigan. You also won’t have to fight with the crowds for a cab to your New Year’s party, like the annual Navy Pier Chicago Resolution Gala; these boots actually are made for walking. Plus, the low heel, padded flannel lining, and extra room in the toe makes it easy to dance all night.
The Socializer
The Boot: Wyat Wingtip Boot
The Destination: Holiday events
This is it: your holiday shoe, a.k.a. the only shoe you’ll need for the office party, date night, and your family dinner. The Wyat Wingtip Boot walks the line between formal and casual: its classic wingtip design feels like a throwback to 1920s dress shoes, while it’s boot height and inside zipper give it an edge that makes it just as easy to pair with jeans and cords as a pair of tailored trousers. Its leather lining and cushioned footbed keep you warm and comfortable for those parties where mingling is synonymous with standing.
Disclosure: This sponsored post is brought to you by Rockport.
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.
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