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.
Stone IslandSI BLUR CREW SWEAT£350.00BelstaffMen's Stride Zip Collar Long Sleeve Overshirt£195.00Stone IslandMen's GD Pocket Cotton Short-Sleeve T-Shirt£265.00CasablancaMen's Mirage Arch Cotton Short-Sleeve Graphic T-Shirt£225.00Tom FordMens Falconer TF0884 Sunglasses£315.00RepresentMen's Eagle Flag Cotton Short-Sleeve Oversized T-Shirt£100.00Stone IslandMen's Cotton Compass Logo Patch T-Shirt£165.00Stone IslandMen's Archivio Graphic Short-Sleeve Cotton T-Shirt£205.00PradaCrossbody Bag£1,500.00Stone IslandMen's Tela Paracadute Cotton Tapered-Fit Cargo Trousers£360.00BelstaffMen's V Racer Water-Repellent Leather Long Sleeve Slim Fit Leather Jacket£725.00Stone IslandMen's Archivio Graphic Short-Sleeve Cotton T-Shirt£205.00PradaSuede Loafers£790.00PradaSymbole Sunglasses£400.00Canada GooseMen's Redwood Square Sunglasses£145.00GucciGucci GG1221S Men’s Rimless Rectangular Sunglasses£385.00GucciGucci GG0529S Men’s Aviator Sunglasses£310.00PradaRectangle Sunglasses£410.00BelstaffMen's Tourer Overshirt£249.00Tom FordMens Dimitry TF0334 Sunglasses£360.00Tom FordMens Fausto TF0711 Sunglasses£315.00PradaMen's 0PS A50S Aviator Sunglasses£315.00PradaMen's Small Crossbody Bag£1,080.00PradaMen'S Plain Nylon Gym Bag£1,580.00Ami ParisLarge Fit Cotton Jeans£310.00Stone IslandMen's T-Shirt£255.00BelstaffLogo Sweatshirt£130.00Cole BuxtonMen's Logo Cotton Sportswear T-Shirt£95.00GucciMen's GG Supreme Canvas Backpack£1,860.00Acne StudiosStamp T-Shirt£360.00BurberryMen's Ryan Big EKD Cotton Graphic Short-Sleeve T-Shirt£375.00BelstaffMen's Stride HdOS Overshirt£249.00Acne StudiosMens 1996 Logo T-Shirt£260.00Stone IslandSI BLUR CREW SWEAT£350.00RepresentMen's Mayhem T-Shirt V2 Oversized Cotton Hemp£95.00BelstaffMen's Insulated Short Puffer Jacket£325.00RepresentMen's Eagle Graphic Cotton Long-Sleeve Oversized-Fit T-Shirt£120.00Stone IslandMen's GH Cotton Cargo Trousers£520.00RepresentMen's Heaven Graphic Cotton Oversized-Fit Long-Sleeve T-Shirt£135.00Stone IslandSI RIPSTOP CARGO TROUSERS£455.00Tom FordMens Fausto TF0711 Sunglasses£290.00RepresentMen's Oversized T-Shirt£100.00GucciMen's Crossbody Bag£1,370.00Ami ParisMen's T-Shirt£150.00CasablancaMen's Hermons Mirage Arch Graphic Short-Sleeve Cotton T-Shirt£225.00Ami ParisMen's T-Shirt£160.00Stone IslandMen's GH Cotton Short-Sleeve Crew-Neck T-Shirt£235.00PradaMen's Cross Body Bags£2,455.00CasablancaMen's Mirage Arch Cotton Short-Sleeve Graphic T-Shirt£225.00CartierCartier Mens CT0132S Wayfarer Sunglasses£555.00PradaMen's Shuffle Loafer£800.00PradaSymbole Sunglasses£375.00

Buy now. Pay later. Earn rewards

Representative APR: 29.9% (variable) Credit subject to status. Terms apply.
Missed payments may affect your credit score.
© 2026 The Flannels Group Ltd

The Flannels Group Ltd (FRN: 977237), trading as ‘Flannels’ is an appointed representative of Frasers Group Financial Services Limited (FRN: 311908) who are authorised and regulated by the Financial Conduct Authority as a lender. Frasers Plus is a credit product provided by Frasers Group Financial Services Limited and is subject to your financial circumstances. For regulated payment services, Frasers Group Financial Services Limited is a payment agent of Transact Payments Limited, a company authorised and regulated by the Gibraltar Financial Services Commission as an electronic money institution. Missed payments may affect your credit score and mean your 0% interest plans end. * Exclusive access to discounts on selected products for Frasers Plus customers before everyone else.