Sperry · Men's Shoes
Gold Cup Prescott Boat Shoes
Boat shoes are back and the Gold Cup is the one worth owning.
$100–$250
Shop Now →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.
Footwear that crosses from beach to dinner
No socks required, no sneakers allowed. Boat shoes for the nautical half of the trip.
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.
Swim shorts worth mourning
Vilebrequin, pre-owned. The French house that has been making the same tailored swim short since 1971, in prints that are the entire point.
Vilebrequin · Clothing
Swim Shorts Sparkling Whales
Vilebrequin swim shorts in the sparkling-whale print.
New
Price at Amazon
See It at Amazon →
Shirts you will not mourn
Linen-style henleys, short-sleeve button-downs and lightweight knits from Coofandy. Holiday clothing takes a beating from salt, sun and hotel laundry, so there is a strong argument for packing things you are not precious about.
The rest of the suitcase
Trunks at the right length, a shirt that survives being folded, and sandals that go from the pool to a table without a change.
Theophilio · Men's Swimwear
Theophilio Gauchos
Wide-legged and unapologetic. Included because the site should have a top end.
$1,000+
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Vilebrequin · Men's Swimwear
Vilebrequin Linen Shirt, Solid
The linen shirt that goes over the swim shorts. Cut properly, unlike most.
$250–$500
Buy This for Him →
Vilebrequin · Men's Swimwear
Vilebrequin Organic Cotton Bowling Shirt
A camp-collar bowling shirt, which is the shape that flatters most men on holiday.
$250–$500
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Vilebrequin · Men's Swimwear
Vilebrequin Riviera Linen Bermuda Shorts
Linen bermudas, which is what men in the South of France actually wear.
$250–$500
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Vilebrequin · Men's Swimwear
Vilebrequin Seaside Life Swim Shorts
The print swim short the house is known for. Side adjusters, no drawstring.
$250–$500
Buy This for Him →
Vilebrequin · Men's Swimwear
Vilebrequin Medusair Swim Shorts
A quieter print, for a man who will not wear turtles.
$250–$500
Buy This for Him →
Vilebrequin · Men's Swimwear
Vilebrequin Hypnoctopus Swim Shorts
A bolder print. Vilebrequin's whole proposition is that you commit.
$250–$500
Get It Here →
Vilebrequin · Men's Swimwear
Vilebrequin Tortues Multicolores Swim Shorts
The turtle print, which is the house's signature and the one people recognise.
$250–$500
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Vilebrequin · Men's Swimwear
Vilebrequin Micro-Perforated Packable Swim Trunks
Packs into nothing and dries in minutes. The technical one.
$250–$500
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COOFANDY · Men's Swimwear
COOFANDY Textured Short Sleeve Button-Down Shirt
Textured weave hides creases from a suitcase. Nineteen dollars and it photographs well.
Under $100
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COOFANDY · Men's Swimwear
COOFANDY Linen Short Sleeve Shirt
Real linen blend, camp collar, sixteen thousand reviews. The holiday shirt, solved.
Under $100
See Price →
Amazon Essentials · Men's Swimwear
Amazon Essentials 7-Inch Quick-Dry Swim Trunk
Seven inches is the flattering length. Quick-dry, twenty dollars, buy the navy.
Under $100
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OluKai · Men's Swimwear
OluKai Nalu Slide Sandal
Hawaiian-made comfort with an adjustable strap. Water-friendly and dressier than a flip-flop.
Under $100
Buy This for Him →
Reef · Men's Swimwear
Reef One Slide Sandal
The cheap pair for the pool that he will not care about losing.
Under $100
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COOFANDY · Men's Swimwear
COOFANDY Knit Sport Coat
An unstructured knit blazer forgives a bad fit and packs without creasing.
Under $100
Shop Now →
COOFANDY · Men's Swimwear
COOFANDY Hawaiian Short Sleeve Shirt
Twenty dollars to find out whether he is a print shirt person.
Under $100
Buy This for Him →
FURTALK · Men's Swimwear
FURTALK Panama Fedora with Wind Lanyard
The lanyard is the feature — hats blow off boats and this one does not.
Under $100
Get It Here →
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.