Finding the right shoes for fall travel can make or break your trip. You need footwear that keeps your feet cozy during chilly mornings, looks great in photos, and won’t leave you limping after a long day of exploring. Whether you’re wandering cobblestone streets in Europe or hiking scenic trails at home, these shoes deliver the perfect mix of warmth, comfort, and style for your autumn adventures.
1. On Cloud 5
Forbes crowned the On Cloud 5 as their best travel shoe overall for 2025, and it’s easy to see why. The breathable mesh construction and slip-on design make airport security a breeze, while the cushioned sole feels like walking on clouds.
While these sneakers lean lighter on warmth, pairing them with thick wool socks transforms them into perfect early-fall companions. Their sleek appearance transitions effortlessly from casual sightseeing to semi-dressy dinners, making them incredibly versatile for travelers who pack light.
2. Vionic Willa II Loafer
Need something dressier without sacrificing comfort? The Vionic Willa II loafer delivers both worlds beautifully. Forbes highlighted this shoe for its exceptional arch support and durable rubber sole that handles city streets with confidence.
The classic loafer silhouette works equally well for business meetings and museum visits. Its structured design provides enough support for moderate walking tours, while the polished appearance keeps you looking sharp throughout your journey.
3. Hoka Clifton 10
When your itinerary involves serious mileage, the Hoka Clifton 10 becomes your best friend. We3Travel featured this shoe in their 2025 fall walking guide, praising its plush cushioning that absorbs impact like a dream.
The signature rocker sole propels you forward naturally, reducing foot fatigue during marathon sightseeing days. Though it has an athletic vibe, the clean design keeps it casual enough for everyday travel wear rather than looking too gym-focused.
4. Rothy’s The Point or Mary Jane Flats
Condé Nast Traveler consistently recommends Rothy’s for their genius packability and instant comfort. These knit flats squish flat in your suitcase without losing shape, saving precious luggage space for souvenirs.
The Point and Mary Jane styles require zero break-in time—just slip them on and go. Their soft construction feels gentle on tired feet after long flights. When temperatures drop, simply add thermal socks to keep your toes toasty without compromising style.
5. Blundstone 550 Chelsea Boots
The Packable Life recommends Blundstone’s iconic Chelsea boots for travelers seeking that sweet spot between style and function. Model 550 slips on effortlessly thanks to elastic side panels, yet provides ankle coverage that lighter shoes can’t match.
These Australian boots handle cooler fall weather beautifully while maintaining surprising comfort for all-day walking. Their rugged construction tackles various terrains confidently, from urban sidewalks to countryside paths, without sacrificing mobility or weighing you down.
6. Birkenstock Boston Leather Clogs
Travel + Leisure named Birkenstock Boston clogs among 2025’s best fall travel footwear, surprising skeptics everywhere. Leather versions with lug outsoles deliver unexpected functionality alongside their signature comfort.
The contoured cork footbed molds to your feet over time, creating custom support that reduces strain. While they work best in dry or lightly damp conditions, adding cozy socks when temperatures dip keeps your feet warm. Their effortless slip-on design appeals to travelers who value convenience without compromising quality.
7. Weather-Resistant Chelsea Boots
Glamour’s 2025 fall shoe roundup emphasizes sleek ankle boots as autumn essentials, particularly Chelsea styles in weather-resistant leather. These boots bridge the gap between fashion-forward and travel-practical beautifully.
Waterproof or water-resistant treatments protect against unexpected drizzle without looking overly sporty. The ankle height provides warmth and coverage while remaining comfortable for extended wear. Their refined appearance transitions seamlessly from daytime exploration to evening dining, making them ideal for travelers with varied itineraries.
