Guide to Classic Vacation Wear

Get inspired by our guide to timeless travel wear for warmer climates.

Light and breezy, with a touch of bright summer colours.

The Basics

A great place to start is with the essential garments you’ll need for your stay, whether you’re at a swanky resort on the Riviera or an all-inclusive hotel with the kids.

The clothing in The Talented Mr. Ripley has inspired countless menswear designers’ summer collections—for good reason. The film’s wardrobe masterfully blends casual ease with timeless elegance.

The Shirt

Resort Shirts

A resort shirt in olive linen, from The Resort Co.

We touched on this classic style in our previous post on shirts, but it would be a crime not to mention it again here. As we’ve outlined before, “resort shirt” refers to a category rather than a single style. The versions we find ourselves reaching for most often are short-sleeved or long-sleeved with rolled-up cuffs.

Terry Cloth Shirts

Co-founder of Pete & Harry, Erik Mannby, walking the cobblestone streets of Florence.

The terry cloth shirt is not only elegant but also highly practical. It’s essentially like wearing a towel—perfect for drying off after a swim or staying cool on a warm stroll.

Polo Shirts

Of course! We can hardly go a post without mentioning this classic summer staple. The polo shirt’s versatility has made it a favorite among everyone from British mods to stylish vacationers in the tropics or southern Europe.

A navy polo is always a solid choice—subtle and elegant. We recommend having at least two: one short-sleeved and one long-sleeved.

The Timeless T-shirt

T-shirts are a fundamental part of popular culture and style, from James Dean in Rebel Without a Cause to Tom Cruise in Top Gun. There are both basic cotton tees and more luxurious knitted options, and each has its time and place when vacationing.

James Dean, one of the first men to popularize the basic T-shirt.
A blue knit T-shirt from Resort Co., paired with Casatlantic chinos, a Jacob Cohen neckerchief, and Bally sneakers.

The Shorts

Do you dare wear shorts in the city, or do you see them strictly as poolside attire? Whatever your stance, every man should own at least a couple of good pairs. A well-fitting pair of shorts should never fall below the knee.

White Shorts

White shorts from Italian luxury brand Brioni.

Originally part of military uniforms, white shorts can often be found in vintage militaria shops. They also have a strong connection to sports like tennis. A crisp white pair always looks sharp—even, dare we say, in the city.

Ghurkha Shorts

Yet another style rooted in military history (as many menswear staples are), Gurkha shorts stand out with their distinctive wrapped waist straps.

Swimming Shorts

So obvious, yet so many choices. What fits your style?

Many men stick to simple black swim trunks, but we encourage a more varied collection. Bright colours and patterns bring a playful touch to beachwear.

Andreas Klow and Erik Mannby enjoying the pool at the beautiful hotel Sina Villa Medici.

The Tailored Menswear

Seersucker Suits, Sport Coats, and Trousers

Whether it’s a suit, a jacket, or trousers, seersucker is a fantastic addition to any warm-weather wardrobe. Italians favour wool variations, while Ivy Style enthusiasts lean toward cotton. Both are excellent choices.

White, Off-White, and Light Beige Linen

Linen is always a smart choice, whether for shorts on a beach promenade or trousers for a sunset dinner. Light tones help keep you cool and pair beautifully with a sun-kissed complexion.

Our friend Simon Berg, mastering the art of wearing a beige linen suit in Florence’s late afternoon summer heat.
Peter Zottolo in a light green linen suit from his tailor in Sicily.
Fredrik af Klercker in a navy linen shirt jacket—a casually tailored vacation essential.

Madras

Named after the city of Madras (now Chennai), this colourful checked fabric was introduced to the West during British colonial rule, though its origins date back to the 17th century. But this isn’t a history lesson—it’s a style guide.

Madras patchwork sport coats are staples in Ivy League wardrobes, but their appeal extends even to Italian menswear enthusiasts.
A madras shirt from Brioni.
Brooks Brothers madras shorts paired with a terry cloth popover and flip-flops—ideal for a day at the beach.

The Accessories

Sunglasses

Whether for sun protection (a must) or pure style, sunglasses are a vacation essential.

The Aviator model has been around since 1935 and few would dispute the iconic status of Ray-Bans version.
The Deckard model from Swedish brand Oscar Magnuson—blending Scandinavian design with practicality and timeless cool.
A classic Persol model, currently sold out at Pete & Harry but hopefully back in stock soon.
Few men can compete with Jack Nicholson when it comes to looking effortlessly cool in sunglasses.

The Panama Hat

Despite its name, the Panama hat originates from Ecuador. It gained its association with Panama during the construction of the canal and has since become the ultimate vacation headwear.

Our friend Kévis Manzi in a wide brimmed Panama hat at Plaza Uomo’s summer event during Pitti Uomo.

Safari Jackets

A tobacco linen safari jacket from Eduardo De Simone, soon available at Pete & Harry.

A perfect blend of a shirt jacket and a field jacket, the safari jacket was designed for warmer climates. Its multiple pockets provide ample space for essentials like your phone, sunglasses, cigars, or anything else that ensures a successful vacation. Opt for one in linen, lightweight cotton, or tropical wool for a look that is both practical and effortlessly elegant.

The Footwear

Though we love black Oxfords, vacation calls for a more relaxed approach to footwear. Here are some elegant yet casual options:

Sneakers

A pair of canvas sneakers from Ralph Lauren – clean design, breezy and comfortable.

A pair of minimalist sneakers will complement nearly everything mentioned above. For a truly timeless look, go for solid-coloured canvas sneakers. Alternatively, if the weather permits, leather or suede options add a refined touch.

Loafers

A pair of casual and lightweight Belgian loafers from Baudoin & Lange.

Loafers are about as formal as you should go on vacation. Shades of brown are always a safe and stylish choice. The most casual option would be a pair of Belgian loafers, but if you prefer something Goodyear-welted, tassel or penny loafers are excellent alternatives.

Masterclass in how to wear loafers in a summer casual style by who else than Cary Grant?

Boat Shoes

Perfect for maritime activities, whether you’re on a yacht or a skiff, boat shoes are a classic vacation staple.

A classic look for adventures at sea.

Sandals

Because no vacation is complete without them.

A Final Note

Of course, this list could go on and on, but we have to stop somewhere. We hope you find this guide to vacation wear helpful!

Since you’re in a foreign place, dare to stand out—at least slightly—by adding a dash of colour to your wardrobe.

And of course, enjoy your vacation with near and dear ones!

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