Orlebar Brown · Men's Swimwear
Bulldog Printed Swim Short
Tailored swim shorts. The reason European men look better at the pool.
$250–$500
Buy This for Him →Build His Vacation Wardrobe · /mens-vacation-outfits/
Build His Vacation Wardrobe
Holiday packing goes wrong in a predictable way: he brings the clothes he wears at home, in a hotter climate, and every photograph looks like a Tuesday. The fix is three or four specifically-for-vacation pieces that do not exist in his normal rotation.
Tailored swim shorts are the single highest-impact item, because they remove the need to change between the beach and lunch. After that: linen, a loafer or a leather sandal, and sunglasses that are not sports wraps.
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The pieces that only exist on holiday
Swim shorts cut like trousers, with a proper waistband. The reason European men look better at the pool.
Persol · Men's Sunglasses
PO3330S Polarized Sunglasses
Straight off our JFK Jr. board. The fastest old-money upgrade there is.
$250–$500
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Footwear that crosses from beach to dinner
No socks required, no sneakers allowed. Boat shoes for the nautical half of the trip.
Ferragamo · Men's Shoes
Byte Gancini Driver Loafers
Fixes his shoe rotation in one move. No socks required, no sneakers allowed.
$500–$1,000
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Sperry · Men's Shoes
Gold Cup Prescott Boat Shoes
Boat shoes are back and the Gold Cup is the one worth owning.
$100–$250
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What it all travels in
Aluminium if he wants the scars to be the point, a wardrobe spinner if a suit has to survive the flight.
Sterling Pacific · Men's Luggage
40L Aluminium Cabin Case
Full aluminium carry-on. Dents become the point, not the problem.
$1,000+
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Briggs & Riley · Men's Luggage
Deluxe Wardrobe Spinner
Lifetime guarantee, airline damage included. The last suitcase he buys.
$1,000+
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Picks from neighbouring collections that fit the same brief.
Creed · Men's Cologne & Fragrance
Aventus Eau de Parfum
The compliment magnet. If he owns one cologne, it should be this one.
$250–$500
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Polo Ralph Lauren · Men's Knitwear
Washable Cashmere Crewneck
Cashmere he cannot ruin in the laundry. Instant Ralph Lauren boyfriend.
$250–$500
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Lucchese · Men's Shoes
Franklin Western Boot
Real bootmaker, not costume Western. Wears with denim and with a suit.
$500–$1,000
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Barbour · Men's Outerwear
Bedale Wax Jacket
The whole aesthetic in one garment. Gets better every year he owns it.
$250–$500
Buy This for Him →
Vacation Outfits FAQ
What should a man pack for a European summer holiday?
Two pairs of tailored swim shorts, three linen or cotton shirts in solid colours, one pair of lightweight trousers, tailored shorts, loafers or leather sandals, and sunglasses. Skip the athletic sneakers and anything technical.
What are the best men's vacation shoes?
Driver loafers for dinner and walking, leather sandals for the beach, and one pair of plain white sneakers if he insists. Three pairs maximum — footwear is what fills a carry-on.
Carry-on or checked?
Carry-on for anything under a week, unless a suit is involved. If it is, a wardrobe spinner with a built-in garment section means the suit arrives at the wedding without a steamer.