Passport? Check. Travel money? Check. Swim shorts? Meh, just pick some up at the airport, right?

Wrong. Swim shorts might seem like the kind of thing you can put on the long finger – they’re just for swimming, right? – but buy badly and you’ll spend most of your holiday awkwardly dodging your mates’ #squad shots.

Buy right however, and not only will you cut a sharp figure with just one piece of clothing on (no mean feat), you’ll have a pair of shorts to wear with the rest of your clothes too. So read on, make notes and find yourself some shorts more swim than sink.

Colour Considerations

But first, a short quiz on colour: do you want to be able to easily team your swim shorts with the rest of your holiday wardrobe?

Yes? Then keep it classic with colours like black, navy, military green and light neutral hues (sand, stone, off-white), or try a subtle blue and white stripe. Opting for a block-colour versatile style – particularly in a standard or tailored cut – means your swim shorts can do double time, working on the beach, by the pool or five rounds in on the dancefloor (just mind you don’t bust the lining).

Not particularly fussed? Feel free to experiment with bolder colours like fire engine red, cobalt blue, canary yellow, pastels and punchier prints like camo, floral, Hawaiian and geometric. All of which act a bit like a bird of paradise mating dance – so be prepared for the attention. (And make sure your body is, too.)

Standard Swim Shorts

What Are They?

What you think of when you think of swim shorts: cut to mid-thigh length, made from quick-drying polyamide, and fitted with an elasticated, drawstring waistband and inner mesh lining for comfort (and to keep the lads together).

Who’re They For?

Everyone. Tall guys, short guys, guys who never skip leg day and guys who have no idea what ‘leg day’ even is.

“A mid-length short in a relaxed fit is the most comfortable and versatile style of swim short,” says Jean-Benoit Evrard, buyer at Menlook. “They work for most body shapes, but opt for a more relaxed cut if you have bigger thighs.”

Like a crew neck tee, a standard pair of swim shorts is a wardrobe all-rounder – unlike some of its listmates, you can’t go far wrong even if you don’t ace the sizing. Still, you can better your chances of a perfect fit by choosing something that’s neither baggy, nor ball-exposingly tight.

j.crew april 2016abercrombie & fitch 2016h&m summer 2016river island ss16

What Do I Wear Them With?

If not totally sporty, these swim shorts definitely lean casual. Which means, once out of the water, whatever you wear them with needs to flow in the same direction.

“Try a premium white T-shirt or a striking tropical print vest for a cool beachwear ensemble,” says Stephen Walsh, menswear junior buyer at River Island. Or, for a slightly smarter alternative, try a polo shirt that skews more sporty than preppy.

Current Styles

  • Asos Swim Shorts With Tropical Floral Print In Short LengthAsos Swim Shorts With Tropical Floral Print In Short Length
  • Abercrombie & Fitch Floral Swim ShortAbercrombie & Fitch Floral Swim Short
  • Asos Swim Shorts With Floral Print In Mid LengthAsos Swim Shorts With Floral Print In Mid Length
  • Ted Baker Seabloc Colour Block Swim ShortsTed Baker Seabloc Colour Block Swim Shorts
  • He By Mango Floral Print SwimsuitHe By Mango Floral Print Swimsuit
  • Uo Swim Embroidered Palm Tree Mint Swim ShortsUo Swim Embroidered Palm Tree Mint Swim Shorts
  • Solid & Striped The Classic Striped Swim ShortsSolid & Striped The Classic Striped Swim Shorts
  • Topman Coral Wiggle Print Swim ShortsTopman Coral Wiggle Print Swim Shorts
  • Reiss Sonny Drawstring Swim ShortsReiss Sonny Drawstring Swim Shorts
  • Saturdays Nyc Grant Mid-length Striped Swim ShortsSaturdays Nyc Grant Mid-length Striped Swim Shorts
  • Mollusk Vacation Mid-length Cotton-blend Swim ShortsMollusk Vacation Mid-length Cotton-blend Swim Shorts
  • Polo Ralph Lauren Traveler Mid-length Printed Swim ShortsPolo Ralph Lauren Traveler Mid-length Printed Swim Shorts

Tailored Swim Shorts

What Are They?

Like regular swim shorts, but spiffier. Often equipped with details like side adjusters in place of an elastic waistband, tab closures and coin pockets, the tailored swim short is perhaps best described as a pair of smart shorts you can swim in.

Some – like Orlebar Brown’s Bulldog – are cut to the same 17-piece pattern as a suit trouser. So expect a snug fit.

Who’re They For?

Not everyone. Owing to tailored swim shorts’ sleek (and sometimes unforgiving) fit across the thighs and in the seat, you’ll need to be lean to do them justice.

By ‘lean’, we mean slim to slightly muscular. If you’re lean but have rugby quads, you might want to look elsewhere because while you can try sizing up, the strict lines of most tailored swim shorts won’t flatter your squat-built pins so much as make them look like sausage meat spilling from its casing. (Hot.)

hackett ss15mango man 2016david gandy for m&sdavid gandy for m&s

What Do I Wear Them With?

Whatever you’d wear with a pair of tailored shorts.

“Try teaming a pair of tailored swim shorts with a lightweight linen shirt or waffle polo shirt for an effortlessly cool look,” says Walsh. “And for that transition from pool to bar, try a suede loafer.”

Smart, clean-lined and trim-fitting, a tailored swim short is the poster boy for beach-to-bar style, pairing effortlessly with Cuban collar shirts, polos and short-sleeved shirts in linen. Buy a pair of these in a versatile colour or pattern and you won’t have to change before posting up for a pre-dinner cocktail.

Current Styles

  • Reiss Ibiza Tailored Swim ShortsReiss Ibiza Tailored Swim Shorts
  • He By Mango Striped SwimsuitHe By Mango Striped Swimsuit
  • Ted Baker Stisho Striped Swim ShortsTed Baker Stisho Striped Swim Shorts
  • Tailored Fit Mid Length Quick Dry Swim ShortsTailored Fit Mid Length Quick Dry Swim Shorts
  • Tailored Fit Short Length Quick Dry Swim ShortsTailored Fit Short Length Quick Dry Swim Shorts
  • Tailored Fit Short Length Quick Dry Swim ShortsTailored Fit Short Length Quick Dry Swim Shorts
  • Hugo Boss Tigerfish Mid-length Swim ShortsHugo Boss Tigerfish Mid-length Swim Shorts
  • Onia Calder Long-length Cotton-blend Shell Swim ShortsOnia Calder Long-length Cotton-blend Shell Swim Shorts
  • Hartford Socoa Mid-length Striped Swim ShortsHartford Socoa Mid-length Striped Swim Shorts
  • Orlebar Brown Bulldog Mid-length Swim ShortsOrlebar Brown Bulldog Mid-length Swim Shorts
  • Orlebar Brown Bulldog Mid-length Printed Swim ShortsOrlebar Brown Bulldog Mid-length Printed Swim Shorts
  • Frescobol Carioca Noronha Slim-fit Mid-length Printed Swim ShortsFrescobol Carioca Noronha Slim-fit Mid-length Printed Swim Shorts

Board Shorts

What Are They?

Boardies. Baggies. Surf trunks. Swim shorts, but longer.

Actually, that’s not entirely true. Board shorts might look like a pair of swim shorts simply extended a few inches, but they’re built differently in two main respects: a) in place of an adjustable waistband, they have a bartacked or velcro fly and drawstring, and b) they don’t always come with a mesh lining.

Who’re They For?

Not just surfers. Or the cast of Home and Away.

“Board shorts have seen a spike in popularity, with surfers being referenced on many of the catwalks for SS16,” says Evrard. (Indeed, Saint Laurent riffed heavily on West Coast cool).

If you’re opting for this traditional surf style, then know that you need both height and bulk to pull it off. Given their length, board shorts can dwarf men 5’10” and under, while their sprawling fabric quickly makes beanpoles out of legs anything less than Olympic lifter beefy.

bhs ss16j.crew ss15simons ss16h&m ss15

What Do I Wear Them With?

Not much. Swim shorts in the truest sense, board shorts aren’t up to much other than kitting you out for catching a few waves. Beach-to-bar these most definitely are not.

Board shorts tend to come in punchy colours and floral/Hawaiian prints too, meaning your best bet if it’s a little too cold to go topless is a simple crew-neck tee, vest or sleeveless tee in white (or a colour complementary to that/those of your shorts).

Current Styles

  • Boardies Coral Board ShortsBoardies Coral Board Shorts
  • Billabong All Day Lo Tides 18.5 Inch Board ShortsBillabong All Day Lo Tides 18.5 Inch Board Shorts
  • Billabong Pulse X Flare 20 Inch Board ShortsBillabong Pulse X Flare 20 Inch Board Shorts
  • J. Crew 9 Board Short In Tropical FloralJ. Crew 9 Board Short In Tropical Floral
  • J. Crew 9 Board Short In Oxford Blue StripeJ. Crew 9 Board Short In Oxford Blue Stripe
  • J. Crew 9 Board Short In Blue PalmsJ. Crew 9 Board Short In Blue Palms
  • Topman Globe Dark Pink Geo Print Shorts Topman Globe Dark Pink Geo Print Shorts
  • Solid & Striped The Boardshort Swim ShortsSolid & Striped The Boardshort Swim Shorts
  • Outerknown Evolution Long-length Printed Econyl Swim ShortsOuterknown Evolution Long-length Printed Econyl Swim Shorts

Speedos/Swimming Trunks

What Are They?

Budgie smugglers. Banana hammocks. Your dad’s swimwear of choice in the 1970s.

Who’re They For?

Tom Daley. Continental Europeans in the best shape of their lives. And no one, we mean no one, else.

goldenpoint ss15nit ss16hom beachwearnit ss16

What Do I Wear Them With?

A shitload of confidence.

Current Styles

  • Tommy Hilfiger Flag Swim TrunksTommy Hilfiger Flag Swim Trunks
  • Speedo Essential Endurance 7cm BriefSpeedo Essential Endurance 7cm Brief
  • Speedo Endurance 7cm Swim TrunksSpeedo Endurance 7cm Swim Trunks
  • Dan Ward Classic Swim BriefsDan Ward Classic Swim Briefs
  • Dolce & Gabbana Classic Swim BriefsDolce & Gabbana Classic Swim Briefs
  • Robinson Les Bains Stanford Stripe-print Swim BriefsRobinson Les Bains Stanford Stripe-print Swim Briefs