What Shoes to Wear for a City Break
31 October 2025
If you’re planning a city break, taking the right shoes can make or break your trip. Whether it’s a romantic weekend in Rome or a cultural jaunt to Paris, a perfect blend of comfort and style will keep you feeling good, however much walking, sightseeing, and exploring is on the itinerary.
In this guide, we’ll help you choose the best shoes for your city break. From the best trainers for walking cobbled streets to comfy sandals that let your feet breathe in the heat, we’ve got all the bases covered.
Here’s what we’ll cover:
- What to look for in city break shoes
- Best shoes for exploring a city break
- Best shoes for different types of city breaks
- How to style shoes for a city break
What to Look for in City Break Shoes
When you're travelling, your footwear does a lot more than just complete your outfit. It's your daily companion on everything from cobbled lanes to grand boulevards, meaning that city exploring demands shoes that go the distance.
Here are some key factors to consider:
Comfort for Walking Long Distances
City breaks usually involve plenty of walking, whether you're sightseeing, shopping, or soaking up the local vibe. Shoes with cushioned soles, arch support, and a fit that suits your foot shape will help keep aches and blisters at bay.
Versatility to Match Different Outfits
With limited suitcase space, it pays to choose shoes that go with multiple outfits. Neutral tones and classic silhouettes can be dressed up or down, making your shoes work harder for you on holiday.
Lightweight and Easy to Pack
Shoes that are bulky or heavy can take up valuable luggage space. Look for styles that are light and flexible enough to fit easily in your bag – especially if you’re flying hand luggage only!
Weather-Ready Materials
From sudden downpours to heatwaves, city break weather can be unpredictable. Look for breathable materials in summer and weather-resistant finishes in cooler months. Always check the forecast and pack accordingly.
Best Shoes for Exploring a City Break
Comfort is the priority, but you also want shoes that look good and can adapt to different settings.
Here are some good options that cover these three bases:
Trainers for All Day Comfort
The best trainers for city breaks are lightweight styles with supportive soles. A good pair of trainers will cushion your feet on long walks while keeping you cool and comfortable. Look for breathable materials and consider neutral colours that work with every outfit in your suitcase.
Top tip: choose trainers with arch support and a flexible sole, as these will help prevent fatigue and keep you comfortable over long distances.
Stylish Loafers for Smart Casual Looks
Loafers are a great choice if you want something that leans toward the smarter without sacrificing comfort. Their slip-on style is great for airport security, too, and they pair well with trousers, dresses, or skirts. Choose soft leather or suede finishes for comfort on the move.
Top tip: break in your loafers before your trip to avoid any stiffness or tightness when you get there!
Sandals for Warm Weather Breaks
If you’re heading on a summer city break, we recommend sandals. A pair with secure straps, supportive footbeds, and soft materials will keep you comfortable and minimise chafing or rubbing. Avoid flip-flops and instead look for styles designed for all-day wear.
Top tip: look for sandals with adjustable straps to get the perfect fit, and consider a small platform or wedge for added support.
Boots for Cooler Destinations
For a city break in the cooler months, ankle boots are a stylish and practical choice. Look for flat or low-heeled styles with cushioned soles and supportive arches. Waterproof or weather-resistant options are ideal if rain is on the forecast.
Top tip: pack boots in a neutral tone to easily match them with jeans, dresses, or trousers.
Best Shoes for Different Types of City Breaks
Different destinations call for different footwear. Here are our top picks based on your type of trip:
Shoes for a European City Break
In cities like Paris, Rome, or Barcelona, stylish comfort is key. A pair of minimalist leather trainers or sleek loafers can take you from museum visits to al fresco dinners with ease. Stick with classic colours and refined designs that fit in with Europe's effortlessly chic street style.
Shoes for a Summer, Beachside City Break
If you're mixing sightseeing with beach days, you'll want a mix of breathable sandals and walkable trainers. Espadrilles or lightweight leather sandals are perfect for coastal cities like Nice, Dubrovnik, or Lisbon. Avoid anything too delicate if you're dealing with sand and sun.
Shoes for a Winter City Break
Cities like Vienna or Prague in winter require warm, weather-proof footwear. Look for flat boots with lined insoles, good grip, and water resistance. If you're heading somewhere with snow, prioritise insulation and non-slip soles.
How to Style Shoes for a City Break
The right shoes can elevate your look while keeping you practical. Here’s how to make yours work hard on holiday:
Day-to-Night Shoe Options
Choose shoes that can transition easily from day sightseeing to evening plans to make the most of your luggage space. A classic leather trainer or a smart suede loafer can easily do double duty with a quick outfit change. Add a blazer or swap casual denim for a dress to refresh your look.
Matching Shoes with Your City Wardrobe
Consider the dominant colours and pieces in your suitcase. Neutral shoes (white, tan, black) will complement most palettes, while bold shoes can add a statement touch if the rest of your wardrobe is understated. Pack socks or tights that pair well with your chosen shoes.
Explore Our Travel-Friendly Shoes
We’re proud to stock a wide range of shoes perfect for city breaks, from lightweight trainers to weatherproof boots and breathable sandals. Whether you’re planning a summer city escape or a cosy winter getaway, you’ll find something stylish and practical to suit.
And if you’re not sure which pair to pick, pop into your nearest store for personalised advice.
