Fall travel means rain, puddles, and slippery sidewalks—but your feet don’t have to suffer. The right waterproof walking shoes keep you dry, comfortable, and confident whether you’re exploring cobblestone streets or hiking through wet trails. From featherweight sneakers to trail-ready hybrids, these twelve picks combine real weather protection with all-day comfort, so you can focus on the adventure instead of soggy socks.
1. On Cloud 5 Waterproof — Light, sleek, city-ready
Speed laces make airport security a breeze. You pull the toggle, slip your foot in, and you’re off—no bending, no fumbling, no wasted time. That alone makes the Cloud 5 Waterproof a favorite among frequent flyers.
But the real magic is how light it feels. Even with full waterproof protection, this shoe barely weighs more than a regular sneaker. Your feet won’t feel weighed down after hours of walking through rainy city streets.
Reviewers consistently praise its all-day comfort and sleek look. You can wear it to a café, a museum, or a casual dinner without looking like you just stepped off a trail. Rain protection doesn’t have to mean bulky boots anymore.
2. Hoka Transport GTX — Urban commuter that loves detours
Built for sidewalks but ready for shortcuts through the park. The Transport GTX handles city miles with ease, yet it won’t complain if you wander onto a muddy trail or gravel path. That versatility is rare in travel shoes.
GORE-TEX waterproofing keeps your feet dry even when puddles are unavoidable. The outsole grips wet surfaces confidently, so you’re not tiptoeing around slick tiles or damp cobblestones. Durability is another standout—reviewers report these shoes hold up season after season.
Comfort is where Hoka shines. The cushioning feels plush without being mushy, and the fit stays secure during long days. If your itinerary includes both urban exploring and occasional nature detours, this shoe adapts without missing a beat.
3. Nike Pegasus 41 GTX — Runner DNA, walker comfort
Nike took its beloved Pegasus and gave it serious weather armor. The GTX edition adds legitimate waterproofing without sacrificing the responsive feel runners love. Even if you’re just walking, that springy cushioning makes miles feel shorter.
Wet-surface traction is where this shoe really delivers. The outsole pattern bites into slick pavement and rain-soaked trails with confidence. You’ll notice it most on those unpredictable fall mornings when everything is damp and shiny.
Yes, it’s slightly heavier than the regular Pegasus, but the trade-off is worth it. Your feet stay dry, your stride stays smooth, and the shoe looks sharp enough for any travel wardrobe. Perfect for travelers who want performance without the bulky boot look.
4. New Balance Fresh Foam X 880v15 GTX — Cushy, grippy, commuter-proof
Plush is the first word that comes to mind. Fresh Foam X cushioning wraps your feet in softness, making long walking days feel less punishing. But don’t mistake cushy for fragile—this shoe is built to handle real weather and real miles.
The GORE-TEX upper blocks rain completely, while the Hydrohesion outsole grips wet surfaces like it’s angry at them. New Balance designed this specifically for slippery conditions, and it shows. No more cautious shuffling across wet tile or damp boardwalks.
Daily trainers usually can’t double as travel shoes, but the 880v15 GTX breaks that rule. It’s supportive enough for all-day wear, waterproof enough for sudden downpours, and comfortable enough that you’ll forget you’re wearing them.
5. Merrell Moab Speed 2 Mid GTX — Feather-light hike-able travel boot
Mid-height boots usually feel clunky. Not this one. Merrell borrowed trail-runner lightness and added just enough ankle coverage to keep debris and rain out. The result is a boot that moves like a sneaker but protects like serious hiking gear.
Waterproof protection extends higher than low-cut shoes, which matters when you’re walking through wet grass or crossing shallow puddles. Your socks stay dry, your ankles stay supported, and your feet stay comfortable even after hours of exploring.
Fall travel often mixes city streets with shoulder-season parks and trails. This boot handles both without complaint. Cobblestones, gravel paths, muddy shortcuts—the Moab Speed 2 Mid GTX adapts to whatever your itinerary throws at it, all while weighing less than you’d expect.
6. Salomon XA Pro 3D v9 GTX — Bulletproof stability for messy weather
Stability is this shoe’s superpower. The XA Pro 3D v9 GTX locks your foot in place with a secure, almost aggressive fit. If you’ve ever twisted an ankle on uneven cobblestones or slippery trails, you’ll appreciate how planted this shoe feels.
Waterproof protection is total. GORE-TEX keeps rain, puddles, and mud outside where they belong. The outsole grips like it’s made of velcro, even on wet rocks or slick tile. Durability is legendary—these shoes outlast most competitors by a wide margin.
The trade-off? A stiffer, more rigid feel. This isn’t a soft, cushioned cloud shoe. It’s protective armor for your feet. Perfect for “city today, castle trail tomorrow” itineraries where conditions change fast and footing gets tricky.
7. Ecco MX Low GTX — Street style, trail grip
Motocross-inspired outsole meets sleek European design. That’s the Ecco MX Low GTX in a nutshell—a shoe that looks sharp enough for a café but grips wet sidewalks like a trail runner. The chunky lugs bite into slick surfaces without looking overly aggressive.
GORE-TEX waterproofing is seamlessly integrated, so there’s no bulky, plasticky feel. Your feet breathe, rain stays out, and the shoe remains light and flexible. Comfort is immediate—no break-in period required, which is rare for leather-based travel shoes.
Versatility is the real win here. Pair it with jeans, chinos, or even casual travel pants, and it works. You can dress it up slightly or keep it sporty. For travelers who want one shoe that handles rain, style, and walking miles, this is it.
8. Hoka Clifton 9 GTX — Pillow-soft miles in the rain
Hoka’s Clifton series is famous for one thing: cushioning that feels like walking on marshmallows. The GTX version keeps that signature softness while adding complete waterproof protection. Your feet stay dry and pampered, even during drizzly, high-step city days.
Lightweight construction surprises first-time Hoka wearers. Despite the thick midsole, the Clifton 9 GTX barely weighs more than a regular sneaker. That means less fatigue over long distances, which is crucial when you’re exploring all day.
Testing roundups consistently recognize this shoe for its balance of comfort and weather protection. It’s not the most rugged option, but for urban travel in cool, rainy fall weather, it’s hard to beat. Your feet will thank you after mile ten.
9. Vessi (Cityscape/Weekend) — Travel-packable knit that’s truly waterproof
Knit uppers that are actually waterproof? Vessi figured it out. Their proprietary fabric blocks rain completely while staying flexible, breathable, and light. Unlike traditional waterproof shoes, these feel more like cozy socks than protective boots.
Airport-friendly design makes them a traveler favorite. They’re easy to slip on, compact enough to pack, and comfortable enough for long security lines and terminal walks. The casual, modern look fits into any travel wardrobe without screaming “outdoor gear.”
Rainy city breaks are where Vessi shines. Puddle-jumping, damp sidewalks, surprise showers—the shoes handle it all while keeping your feet comfortable and dry. They’re not built for rugged trails, but for urban exploring in wet weather, they’re nearly perfect. Plus, they’re machine washable, which is a bonus after muddy adventures.
10. Allbirds Wool Runner-up Mizzles — Cozy, water-repellent, low-key style
Merino wool might not sound like rain protection, but Allbirds treated their wool upper to shed water surprisingly well. It’s not full GORE-TEX armor, but it handles light rain, drizzle, and damp conditions without soaking through. Plus, wool naturally regulates temperature, keeping feet warm without overheating.
Sustainability is part of the appeal. Allbirds uses eco-friendly materials and carbon-neutral production, so your travel footprint shrinks a bit. The low-key, minimalist style works with almost any outfit, making them easy to pack and wear daily.
Comfort is instant and effortless. No stiff break-in, no hot spots, just soft, cozy walking. They’re perfect for travelers who prioritize comfort and sustainability, and who need decent rain protection without the bulk of traditional waterproof shoes.
11. Keen Zionic NXT Mid Waterproof — Fall-proof grip and dry feet
A reviewer walked fifty miles through streams and glaciers—and stayed dry and blister-free. That’s the kind of real-world testing that builds trust. Keen’s KEEN.DRY waterproofing is serious business, blocking moisture even in extreme conditions.
Multi-directional lugs on the outsole grip everything: wet rocks, muddy trails, slippery sidewalks, icy boardwalks. If your “city break” includes unpredictable weather or off-the-beaten-path exploring, this shoe won’t let you down. The mid-height design adds ankle support and extra coverage against rain and debris.
Durability is Keen’s trademark. These shoes take a beating and keep performing season after season. They’re not the lightest option, but when weather turns nasty and footing gets sketchy, you’ll appreciate the solid, protective feel. Perfect for travelers who refuse to let weather dictate their plans.
12. Hoka Challenger 7 GTX — Door-to-trail versatility
Pavement-friendly comfort meets trail-ready traction. The Challenger 7 GTX straddles that line beautifully, making it ideal for destinations where you’ll walk city streets one hour and explore muddy park paths the next. Versatility like this is rare—and incredibly useful for travelers.
Waterproof GORE-TEX protection keeps feet dry without adding bulk or stiffness. The midsole cushioning is stable and responsive, so you’re not sacrificing comfort for durability. Comparative testing highlights this shoe’s ability to handle varied terrain without feeling like a compromise.
If your fall travel includes parks, nature reserves, or towns with unpaved shortcuts, the Challenger 7 GTX adapts seamlessly. It’s stable enough for uneven ground, cushioned enough for long pavement walks, and waterproof enough for surprise rain. One shoe, many adventures.
