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.
CasablancaMen's Graphic Cotton L'Arche Tennis Club T-Shirt£169.00RepresentMen's Owners Club Oversized Fit T-Shirt£90.00CasablancaMen's Regular Fit T-Shirt£199.00RepresentMen's Owners Club Oversized Fit T-Shirt£90.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00Stone IslandMen's Graphic Cotton Short-Sleeve T-Shirt£205.00Cole BuxtonMen's Inter Logo Oversized T-Shirt£75.00CasablancaMen's L'Arche Classic Cotton Short-Sleeve T-Shirt£225.00BelstaffMen's Water-Repellent Wax Jacket£295.00Cole BuxtonMen's Inter Logo Oversized T-Shirt£75.00Stone IslandMen's GD Cotton Overshirt£430.00BurberryMen's Regis Check Cotton Trainers£625.00RepresentMen's Rep Owners Club Vintage-inspired Sweatshirt£140.00GucciGucci GG1856S Men’s Aviator Sunglasses£195.00Stone IslandMen's GD Cotton Overshirt£430.00CasablancaMen's Hotel Emblem Short-Sleeve Cotton T-Shirt£225.00PradaMen's Chocolate Metal Hardware Contoured Footbed Loafers£860.00PradaMens Boat Shoes£780.00PradaMen'S Plain Cotton Badge Pocket T-Shirt£630.00GucciGucci Mens GG1732SK Wayfarer Sunglasses£350.00BurberryMen's Ryan Short-Sleeve Cotton T-Shirt£395.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00CasablancaMen's Classic Logo T-Shirt£149.00CasablancaMen's Classic Logo T-Shirt£149.00Stone IslandSI CLASSIC BADGE CREW£295.00BurberryMens Check Trim Cotton T-Shirt£355.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00Stone IslandSI VERTICAL GRAPIC TEE£205.00RepresentMen's Owners Club Oversized Fit T-Shirt£90.00BelstaffPhoenix T-Shirt£60.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00Ami ParisMens De Coeur T-Shirt£120.00Ami ParisMens De Coeur T-Shirt£120.00GucciMen's GG Supreme Canvas Backpack£1,790.00GucciMen's Crossbody Bag£1,400.00Stone IslandMen's Overshirt£495.00CasablancaMen's Classic Logo T-Shirt£149.00Stone IslandMen's Ghost Crew Cotton Sweater£350.00Stone IslandMen's Crinkle Reps Bomber Jacket£625.00Stone IslandMen's Cordura Puffer Jacket£1,040.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00Ami ParisMen's Cotton Short-Sleeve Crew-Neck T-Shirt£190.00Stone IslandMen's Tela Paracadute Cotton Tapered-Fit Cargo Trousers£360.00Stone IslandMen's Crinkle Reps Hooded Bomber Jacket£860.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00BelstaffMen's Fieldmaster Water and Wind Resistant Cotton Long Sleeve Wax Jacket£495.00PradaMen's Crew Sweatshirt£1,200.00Cole BuxtonMen's Logo Cotton Sportswear T-Shirt£75.00RepresentMen's Owners Club Oversized Fit T-Shirt£90.00RepresentMen's Owners Club Oversized Fit T-Shirt£90.00Ami ParisMens De Coeur T-Shirt£120.00Stone IslandMen's GD Cotton Overshirt£430.00

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