Top 10 Most Comfortable and Durable Shoe Types for Long City Breaks

Alright, let’s talk shoes—because if there’s one thing I’ve learned from countless city breaks, it’s that what’s on your feet can make or break the whole experience. No one wants to be hobbling back to the hotel after a full day of sightseeing just because they thought cute but blister-inducing shoes were a good idea.

Trust me, I’ve been there. So, to save you from making that same rookie mistake, here’s a breakdown of the top ten most comfortable and durable shoes that’ll keep your feet happy no matter how much ground you’re covering.

1. Walking Sneakers: Your MVP

When I say walking sneakers are essential, I mean essential. You don’t want to be halfway through your day and feel like you’ve been wading through quicksand because your shoes don’t have enough support. I’m talking about sneakers that cradle your feet like a memory foam mattress. 

Look for breathable fabrics like mesh—because sweaty feet are nobody’s friend—and lightweight designs so you don’t feel like you’re dragging your feet through the city. Brands like New Balance and Skechers have nailed the combo of comfort and style, so you can look good while pounding the pavement.

2. Trail Running Shoes: The Cobblestone Conquerors

Ever been on one of those charming European streets that looks like it hasn’t been repaved since the 1600s? Yeah, that’s where trail running shoes come in. They’ve got the grip and durability to handle cobblestones, uneven paths, and whatever else those historic streets throw at you. 

The tricky part is that you will have a difficult time cleaning trail running shoes. It’s almost essential to use a white sneaker cleaner kit because otherwise, you will need to use up all the soap in the house. Nonetheless, I swear by brands like Salomon and Merrell when I know I’ll be trekking through rougher terrain.

3. Slip-On Sneakers: Lazy in the Best Way

Listen, sometimes you just don’t want to deal with laces. Slip-on sneakers are your go-to when you need a no-fuss, comfy shoe for a city break. I’ve done the whole “sit on the curb to tie my shoes” routine one too many times—never again. 

Vans and TOMS have perfected the art of the slip-on, giving you cushioned soles and an effortless vibe. Plus, they’re super easy when you’re zipping in and out of shops or cafes.

4. Waterproof Hiking Boots: Be Prepared (But Stylish)

I learned the importance of waterproof hiking boots the hard way—caught in a downpour in Amsterdam with soaked sneakers. Let me tell you, there’s nothing worse than squishy shoes. Waterproof hiking boots are perfect for city breaks where you might hit some trails or face unpredictable weather.

Columbia and Timberland are top-tier for this—they’re not just functional, they’re actually cute. Who knew hiking boots could be versatile enough for both a rugged walk and a casual stroll?

5. Comfortable Sandals: Warm-Weather Wonders

If you’re heading to a city with warm weather, a solid pair of sandals with arch support is a must. And by “solid,” I don’t mean those flimsy flip-flops that leave you with sore arches by lunchtime. 

I’m talking Teva and Birkenstock level, where you can walk all day and still feel like you’re on a cloud. Look for cushioned soles and adjustable straps for that perfect fit. I’ve worn my Birks around Europe in the summer, and honestly, my feet have never been happier.

6. Athleisure Sneakers: Style Meets Comfort

Athleisure sneakers are my favorite double-duty shoes—one minute you’re wandering through a museum, the next you’re heading to dinner, and these kicks can handle it all. They give off just enough sporty vibes without making you look like you’re about to hit the gym (unless you are, then no judgment). 

Nike and Adidas have nailed this trend, offering lightweight sneakers that are so comfy, you’ll forget you’ve been walking for hours. These are especially great if you’re packing light and need one pair of shoes to handle a full day’s worth of adventures.

7. Low-Top Hiking Shoes: The In-Betweeners

Can’t decide between sneakers and hiking boots? Let me introduce you to low-top hiking shoes, the perfect middle ground. They give you the durability of hiking boots but feel more like sneakers. These are a godsend in cities where you’ll be walking on both flat streets and steep inclines. 

KEEN and The North Face offer low-top hiking shoes that are so versatile, you’ll wonder how you ever lived without them. I rocked a pair in San Francisco (those hills are no joke) and they made all the difference.

8. Chukka Boots: Stylish but Comfy

Chukka boots are for when you want to look a little more polished without sacrificing comfort. I wore a pair on a city break to London, where one minute you’re wandering through parks and the next you’re headed to a nice dinner. 

These boots have a relaxed, stylish vibe, and with brands like Clarks and Timberland in the mix, you know they’re built to last. They’re the kind of shoes that work with pretty much any outfit—bonus points for versatility!

9. Espadrilles: Summer Vibes Only

If your city break is somewhere warm, espadrilles are the way to go. They’re lightweight, breathable, and just scream “vacation mode.” I’ve worn espadrilles for strolling through seaside towns and open-air markets, and they’re the perfect mix of comfort and casual chic. 

Brands like Soludos and TOMS offer espadrilles that have cushioned insoles, so your feet are just as comfortable as they are stylish. Plus, they’re so easy to slip on and off, you’ll be breezing through your trip.

10. Casual Loafers: The Sneaker Alternative

If sneakers just aren’t your thing, casual loafers are your next best bet. They offer sneaker-level comfort but with a more refined look, perfect for when you want to step up your style game without torturing your feet. 

Cole Haan and Rockport have some seriously comfortable loafers that are great for a full day of walking followed by a fancy dinner. I’m all about footwear that transitions seamlessly from day to night, and loafers do exactly that.

Wrapping It Up: The Shoe Matters

So, what’s the moral of the story? Don’t skimp on shoes. Whether you’re hitting cobbled streets in Europe or navigating a sprawling cityscape, the right pair will make sure your feet (and mood) stay happy. Invest in good, durable footwear and I promise your future self will thank you. Your feet do a lot of work on a city break, so give them the support and comfort they deserve—and hey, look good while doing it!