Best Shoes for a City Break (That Won’t Wreck Your Feet)

Planning a city break? Whether it’s a weekend in Paris, a food tour of Lisbon or a few days in Rotterdam, there’s one thing all city breaks have in common: you walk. A lot. Exploring museums, hopping on and off trams, strolling through old quarters and discovering hidden cafés – it’s not unusual to rack up 20–30,000 steps a day. So your shoes need to be comfortable, supportive and still look cute in all those holiday snaps – luckily for you, I've found the best shoes for a city break (that won't wreck your feet!).

After countless city breaks over the years, I’ve learned the hard way that your footwear can make or break your trip. Blisters, aching arches or bulky shoes that ruin your outfits? No thanks.

I remember being on a city break in Lisbon and I hadn't realised how slippery the stone streets are when you're climbing the hills. Don't be like me slipping and sliding down the roads – do your research and go prepared for your trip. If you're dealing with old cobblestoned streets – pack trainers with grip and that will be comfortable instead of the pretty sandals that will leave you with blisters.

Keep reading for my best footwear tips for your next trip! In this guide, I’ll share exactly what to look for in the best shoes for a city break – plus an exclusive discount code for a brand I think you'll love. This blog post is a paid partnership with HEYDUDE – but I'll only ever share my best recommendations with you guys. [AD] 

What to Look for in the Best City Break Shoes

City break style is all about blending comfort and fashion. You’ll likely be in trainers or flats all day but still want to feel chic for rooftop cocktails or dinner in the evening. If you're just travelling for a weekend or a few days, it's also worth thinking about how minimally you can pack. Squeezing your luggage into a backpack or carry-on means beating the extra luggage costs for checking a bag – which leaves you more money to spend on cocktails (girl math!).

Here’s my checklist:

1. All-Day Comfort – Look for cushioned insoles and lightweight soles that support you through thousands of steps.
2. Breathability – City trips can get hot; breathable fabrics keep feet fresh.
3. Neutral Colours – White, beige, black or soft grey go with everything, saving you from packing multiple pairs (or go for a pop of colour that will work with all your outfits!)
4. Lightweight – Easy to throw in a carry-on, and won’t feel like bricks by day two.
5. Easy to Slip On & Off – Perfect for airport security, train travel and long sightseeing days.
6. Fashion-Forward – A streamlined trainer or trainer style works with jeans, dresses and skirts.

Top tip: Remember when you arrive on a city break – you can't always check in or leave your luggage right away – so packing light and keeping to just the essential shoes can make all the difference if you have to carry your bag around the city!

My City Break Shoe Pick: HeyDude Karina Duo Classic

On my most recent city break to Rotterdam, I clocked up more than 60,000 steps exploring the museums, cruising the canals and even joining a vegan food tour and street art walking tour! I had so much fun, but my feet were aching after day 1 in my boots and I knew there must be a better option for my next city escape. I've decided to test-drive the HeyDude Karina Duo Classic trainers and will be taking them on my next city break – but here's what I'm loving so far:

Here’s why they are a game-changer:

• Featherlight: Seriously, these trainers weigh next to nothing.
• Cloud-Like Cushioning: The foam insole gave the extra support I needed – no aching arches.
• Slip-On Design: I loved how easy they were to pull on before heading out.
• Versatile Style: I went for a pop of pink and they went with every outfit – from my midi dresses to jeans.

Who are HEYDUDE? They're a brand that is on a mission to share the lightest, softest shoes on Earth to make you feel you’re walking on air. HEYDUDE are redefining comfort and versatile footwear – but I love that this doesn't mean boring shoes! Life is too short to wear shoes that are boring – but when you love chasing adventures like me, you need shoes that are comfortable and will keep you on your feet.

I'm loving trying out their trainers – but they have so many styles to try including their classic Wally and Wendy styles, and they now have the cosiest slippers that have just arrived in time for hibernation season, so don't forget to check out their newest collections. With Black Friday and Christmas just around the corner – it's the perfect time to treat yourself – or find a gift for someone special using my 20% off discount code!

How to Style Trainers for a City Break

One of the best things about a versatile trainer like the Karina Duo Classic is how easily they pair with city-break outfits:

• Daytime Exploring: Wear with relaxed linen trousers, a tee and crossbody bag.
• Evening Drinks: Switch to a midi dress or tailored jumpsuit – these trainers still look polished.
• Airport Travel: Team with leggings and an oversized hoodie for ultimate comfort.

Depending on your style – you could go for a neutral shade for a more understated look and add your personality with colourful socks or accessories without worrying about clashing. Or, if like me, you love a pop of colour, you could go for the pink pair to stand out in the crowd.

Other Types of Shoes Worth Packing for a City Break

If you have a bit more space in trainer like the HeyDude Karina Duo Classic will be perfect for most outfits, having one or two back-up options can make your trip smoother (and more stylish). Here are my go-tos:

Dressy Flats, Low Heels or Loafers

Perfect for fancier evenings out, museum visits or more formal restaurants where you don’t want to wear trainers. Choose a soft leather or cushioned footbed so you can still walk comfortably.

Lightweight Sandals

If you’re travelling somewhere warm, pack a supportive sandal with straps. Great for the beach, hotel pool or casual evening strolls. 

Ankle Boots (Weather-Proof)

For cooler climates or unpredictable weather, a low, flat ankle boot adds a bit of polish and keeps your feet dry. Opt for a classic black, chocolate brown or neutral shade to work with all your outfits.

Foldable Ballet Pumps

Handy for slipping in your day bag if you need to switch out of trainers for dinner or drinks. They take up hardly any space in your luggage.

Gym or Running Shoes (Optional)

If you plan to squeeze in a workout or a morning jog, bring a separate pair of lightweight running shoes so your sightseeing trainers don’t get worn out.

Packing Tip: Two pairs (a trainer plus one of the above) usually covers everything. Choose neutral tones so you can mix and match outfits easily.

Other City-Break Shoe Tips

Before you pack for your trip – make sure you read these tips so you don't make the same mistakes I have on previous city breaks! Here's my hot tips to help you prepare for your city break and make the most of it:

• Break Them In: Even the comfiest trainers deserve a short test-run before your trip.
• Pack Blister Plasters: Just in case – though I didn’t need any with my HeyDudes.
• Consider Insoles: If you have high arches or special needs, pop in a custom insole for extra support.
• Limit to Two Pairs: A comfy trainer + a dressier sandal or flat for evenings is usually plenty.

Why I’ll Be Packing HEYDUDE Again

Comfortable, stylish, lightweight and perfect for travel – the Karina Duo Classic has earned a spot in my carry-on for my next city break and trip to the airport. If you’re planning your own getaway, trust me: don’t compromise on your footwear. Your feet (and your Instagram photos) will thank you.

Exclusive Offer: Use code LUCY-20-OFF for 20% off – shop now!