Cold weather travel is the hardest to pack for. Between thick sweaters, heavy jackets, and bulky boots, you need way more suitcase space than for a warm-weather trip where you just have to throw in a few light layers, sandals, and sunscreen. That’s why it’s important to find the perfect pair of boots that multitask for every part of your trip, so you only have to pack one pair. And, ideally, they’re comfortable enough to wear on the plane, saving you even more space.
We tested out the best fall and winter travel boots for walking, wearing them for many miles on the road to make sure they’re comfortable, stylish, and durable. These are our favorites that we’ll be packing for the future.
Best Women’s Travel Boots
L.L. Bean West End Boots
If you’re packing thicker pants or simply struggle to find boots that aren’t too tight, L.L. Bean’s West End Boots are a great pick. These stylish, tall boots have a wider-than-average leg opening and work under pants or layered over tights.
The full-grain waterproof leather upper will keep you dry in downpours, and rubber pods on the outsole add traction and durability to keep your footing secure, all without looking like a rain boot. Inside, the soft leather lining and True Comfort footbed are great for walking for miles.
Nisolo Viola Moto Boots
When you want to blend right in in a stylish city, wear the Nisolo Viola Moto Boots. The pull tabs make these boots easy to slip on and off, so they’re great for the plane (or for airport security, where you may still have to remove boots despite the recent change to the “shoes-off” rule.)
A 45mm heel and a roomy 170mm shaft, paired with a leather-lined memory foam footbed, provide just the right amount of lift and padding to make these comfortable to walk in all day.
L.L. Bean Camden Hill Alpine Boots
For trips where snow or ice is in the forecast, L.L. Bean’s Camden Hills Alpine Boots are our go-to. They’re lined with a 75% wool, 25% lyocell blend over a wool-covered footbed, making them feel like our favorite slippers and keeping feet warm and cozy. The exterior is full-grain leather, and a mini-lug VertiGrip rubber outsole keeps traction solid on slush and ice.
A side zipper gets you in and out without unlacing, and L.L. Bean includes a second set of laces in case you want to switch up your look. The stylish design has garnered us many compliments every time we wear them.
Best Men’s Travel Boots
Danner Pine Grove Chukka
If you’re looking for a buy-it-for-life travel boot, look no further than Danner’s Pine Grove Chukka. Built in Danner’s Portland factory with the finest materials from around the world, the Pine Grove Chukka is designed to last and is genuinely recraftable, meaning Danner will replace parts and restitch the leather instead of you having to buy a new pair.
A steel shank underfoot and Danner’s own Wedge outsole add comfort on smooth surfaces like sidewalks and airport floors.
Red Wing Classic Moc Boots
There’s extra room in the forefoot and instep of these Classic Moc Boots for a good, comfortable fit, thanks to Red Wing’s No. 23 last. This last was created in the 1950s and is still the brand’s most iconic fit.
The leather is a Goodyear welt with Puritan triple stitching and Red Wing’s signature Traction Tread rubber outsole, a combination that’s held up since the boot debuted, for a classic, stylish look that won’t make your travel pictures look dated.
Grant Stone Diesel Boots
Grant Stone’s Diesel Boots use high-quality leather for a water-resistant boot that’s comfortable. The build goes deep, with brass eyelets and speed hooks, a full leather lining, cork filler underfoot, and a steel shank for support, all built on Grant Stone’s “Leo” last.
The welt itself is vegetable-tanned leather, which is what makes the boot resoleable for years rather than disposable.
What to Look for in a Travel Boot
Comfort over distance matters more than comfort standing in a store. Beyond that, look for good traction on wet or uneven ground, a boot that’s easy to slip on and off for security, and a style versatile enough to wear with more than one outfit so it’s not a one-trip boot.
Packing Tips for Travel Boots
Wear your boots on travel days instead of packing them. If you do need to pack a pair, stuff the inside with socks or a scarf to keep their shape and avoid wasting suitcase space.
FAQ
Are leather boots good for travel?
Yes, especially waterproof or water-resistant leather. They handle rain and light snow well, break in over time to fit your foot, and tend to look better with age instead of worse.
How do I choose a travel boot that works for multiple outfits?
Look for a low or minimal heel, a neutral color like black or brown, and a silhouette that isn’t overly casual or overly formal. Boots that strike a balance work with both jeans and a dress.
Should travel boots be broken in before a trip?
Yes. Wear them around your house or on short errands for at least a week before your trip so you know exactly how they feel over hours of walking, not just minutes.
