It’s City Break Season & Here’s Your Shopping List

New Balance

It’s city break season which means that your holiday wardrobe needs to be the best it’s ever been. Sure, it’s nice looking good on your beach holiday, but realistically that just means a good pair of swim shorts and a breezy shirt. City break outfits require a little more thought and finesse, not only because of the activities but also because you’re showing out for a new city.

Versatility is the name of the game for the best city break outfits. In a single day, you might be traveling, hitting a gallery, bar, and restaurant. That calls for an outfit that does a bit of everything, looks great, and feels comfortable.

Below, our Market Editors have put together three city break outfits for big occasions from SSENSE. Using names like Sunnei, Jacquemus, Satisfy, and Birkenstock, they’ve rounded up a list of pieces that can guide you to city break success.

Shop 3 city break outfits from SSENSE.


Where better to begin than with a perfectly sized cabin suitcase from Floyd? Using the same polyurethane wheels you’d likely find on a skateboard, Floyd’s suitcases are the ideal companion for a smooth ride through your city of choice.

Traveling outfit

Traveling is a major part of your city break. If you’re only there for a few days, then making sure that your travel is quick and easy is essential. An oversized hoodie from Sunnei is the obvious starting point. Kenzo denim shorts provide comfort but avoid looking scruffy. On the feet, a pair of trusty Birkenstock Bostons ties this easygoing look together.

Embroidered Hoodie
Denim Shorts
Boston Clogs

Going for dinner

You’re going to scrub up a bit for dinner, but that doesn’t mean going over the top with formal styles. Jacquemus’ Surchemise Matelas in white gives the effect of a crisp white shirt but its woven fabric provides layering possibilities. Bold green workwear-style pants from Specer Badu are the bold centerpiece of this outfit, with Marni loafers singing the final note.

La Surchemise Matelas
Wide-Leg Trousers
Moccasin Loafers

Exploring the city

You’re in a new city to explore it, finding the best restaurants, bars, and hidden gems. That involves a lot of walking, so your exploration outfit needs to be the most comfortable of the lot. We’re looking to Satisfy’s running expertise here. The distressed tee features breathable holes to the chest. The and Wander pants usher in a technical flavor with the possibility to zip off the bottom half to make shorts.

Footwear is the crux of a good exploration outfit, and what better to lead you around a new city than On’s Cloudstratus which genuinely feels like you’re walking on clouds.

Distressed T-Shirt
Trek 2Way Trousers
Cloudstratus Sneakers

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