Men's City Break Outfits

Discover our edit of men’s city break outfits curated for afternoons exploring new neighbourhoods, late dinner reservations and weekends spent navigating the streets of your next destination. From spring trips to Rome to summer weekends in Madrid and autumn escapes to Edinburgh, find city break outfit ideas designed for every type of getaway. Keep daytime looks contemporary with tees by Casablanca or Represent, paired with Acne Studios jeans and Burberry trainers, ideal for long days walking around the city without compromising on style. For cooler evenings and changing weather, layer a lightweight jacket or an overshirt by Stone Island over a sweatshirt for an easy extra layer whilst travelling. Complete your look with designer sunglasses by Prada and Gucci, suited to rooftop drinks, outdoor cafés and sightseeing in the sun. Whether you’re packing for a short European break or planning outfits for a longer trip abroad, discover men’s city break outfits designed to work from daytime exploring through to evening plans.