If you’re lucky enough to be leaving the English downpour for a warmer climate this summer, I envy you. For me, there’s nothing better than the sunbathing/party/hangover cycle in a discounted paradise; whether it’s a luxuriously relaxed, cultural affair with the family or an outright week of self-annihilation with the mates, I love holidays.

Let’s be honest, what’s not to love? All this off-shore indulgence brings plenty of perks, but simultaneously presents many conundrums for the jet-setting gent. Did you remember to sort out health insurance? Will the hotel really look like the brochure? Is it safe to crack jokes at the airport check-in desk? And, most importantly, what should you pack in the perfect holiday suitcase?

I can’t provide much advice on your own safety (and subsequent financial repercussions) or airport security etiquette, but I can give you a little guidance in the form of this Holiday Style Survival Guide: everything you need to know about looking your best whilst abroad. With all the fashion essentials one holidayer needs, a few basics will ensure you’ve got an impeccable look to match your impeccable tan (or enough style points to counter the comedy sunburn.)

1. Swimshorts

The essential piece of holiday kit – these will get more use than any other clothing in your suitcase. Holidays always guarantee plenty of poolside dips and beach bathing, making a quality pair of swimshorts essential. Needless to say, you get what you pay for, and there are plenty of price ranges to cater to everybody’s budget.

Many believe “swimshorts are just swimshorts” – a grave mistake. It’s incredibly easy to get it all wrong, and looking good shouldn’t be limited to dry areas only. Novelty Bermuda shorts are plain offensive: you don’t want to look like an extra from American Pie. Also, neon-Hawaiian prints aren’t cool, or retro, or ‘rad’. They’re just embarrassing.

By the same token, the banana hammock budgie smugglers are not flattering: they weren’t in the 80s, they weren’t in the 90s, and guess what, they aren’t now and never will be. Speedos are, simply put, unacceptable. Looking creepy ain’t a turn-on.

My advice: always go for the mid-thigh classic style. You really can’t go wrong. Block stripes and plain colours are the trophies of simplicity, and it’s always far better to select a timeless style over short-lived trends. You won’t be hard-stretched finding a pair that really suits your own tastes, and almost every brand (be it designer or high street) have their own take of this classic piece of swimwear.

Keep it simple, keep it understated. What would you rather be: 007 diver or Anchorman ‘Cannonball’? It’s really not that difficult.

  • Asos Swim ShortsAsos Swim Shorts
  • Polo Ralph Lauren Hawaiian Swim ShortsPolo Ralph Lauren Hawaiian Swim Shorts
  • Burton Bright Pink Swim ShortsBurton Bright Pink Swim Shorts
  • River Island Multi Stripe Swim ShortsRiver Island Multi Stripe Swim Shorts
  • Lyle & Scott Blue Block Stripe Swim ShortsLyle & Scott Blue Block Stripe Swim Shorts
  • American Apparel Tri-color Swim TrunkAmerican Apparel Tri-color Swim Trunk
2. Flip Flops

In my opinion, holidays are the only acceptable time to don flip flops. I think they’re really quite ridiculous: hearing that familiar pitter-patter down university corridors made my blood boil (especially mid-December). Being abroad dilutes my usual hatred for the flip-flop however, and they’re perfect for daytime strolls and pool breaks.

My first port of call would be the good old Havianas; recognised, reliable, the Ryan Gosling of the flip flop world if you will. This being said, they’re not the cheapest option, and splashing the cash on such footwear isn’t exactly feasible when they see little use outside of your holiday. (If they do, then I am strongly judging your style choices).

Simplicity and comfort are the crucial factors when choosing your ideal flip-flop, as there’s nothing worse than blisters in between your toes – believe me. Go for something inoffensive, (preferably not neon/tiki-themed) that you can wear with ease, and you can get a decent pair at cut-rate prices from the likes of Primark, Matalan and Peacocks. The secret to a solid flip-flop choice is to not think about it too much, after all, they are only flip flops.

N.B. Flip flops painful no matter what you do? Try rubbing a little Vaseline onto the part that goes between your toes – works an absolute dream.

  • Havaianas Brasil Flip-flopsHavaianas Brasil Flip-flops
  • Topman White Ipanema Flip FlopsTopman White Ipanema Flip Flops
  • Topman Blue Smart Flip FlopsTopman Blue Smart Flip Flops
  • Reef Skyver Leather Flip Flops BrownReef Skyver Leather Flip Flops Brown
  • Basic Flip FlopsBasic Flip Flops
  • Blue Harbour Toe Post Flip-flopsBlue Harbour Toe Post Flip-flops
3. Night Shoes

Donning your flip flops by the poolside or on daytime walks is fine. But on an evening? Well, that’s just pure style laziness. Sure, you’re on holiday, let’s chill out blah blah blah, but nothing says ‘uni banter idiot’ more than a pair of flip flops in a nightclub. (Not sure if you’ve cottoned on yet to my feelings surrounding them…)

Take at least one other form of footwear. It’s essential. There are plenty of heat-friendly options this season that simultaneously ensure looking and feeling cool, and a certain smartness can be attained without the need for hyperformality.

On the more casual side of the spectrum, Converse with short-shorts is a strong and classic look without appearing like you’ve tried too hard. A pair of white, cream, red or blue are a safe option that will go with most things in your suitcase; the American brand has remained on the style radar for decades now, and the inclusion of an iconic brand can transform a ‘good’ outfit into a ‘classic’ outfit.

Trainers are also encouraged, however, exercise caution. Think more Adidas Samba, less Nike Air Max – we want style, not chav in Kavos. Onitsuka Tiger trainers are also a great choice; a recognisable yet an unobvious decision. If you’re avoiding the risk of ruining a great pair of sneaks (can easily happen whilst on holiday), school-style plimsolls are a fantastic and relatively affordable option from ASOS, Topman and other major retailers.

If you’re looking for something a little smarter, try the tasselled loafer or a driving shoe. Going sockless is essential though, so keep that in mind – you’ll go from cool guy to gimpy granddad in a matter of seconds if this rule is ignored.

Navy, camel and browns are the key shades here, and opt for suede or relaxed leather to keep things from going overboard; we want to be the right side of casual, and there’s no room for suit territory in the holiday suitcase. Leave the brogues at home.

  • Leather Stain Defence™ Lace Up Boat Shoes With Silver TechnologyLeather Stain Defence™ Lace Up Boat Shoes With Silver Technology
  • Topman Teak Suede Tassle LoafersTopman Teak Suede Tassle Loafers
  • Topman Dispair Leather LoafersTopman Dispair Leather Loafers
  • Converse Chuck Taylor Canvas SneakersConverse Chuck Taylor Canvas Sneakers
  • Mens Onitsuka Tiger Mexico 66 TrainersMens Onitsuka Tiger Mexico 66 Trainers
  • Vaughan Saddle Plimmy Polo Ralph LaurenVaughan Saddle Plimmy Polo Ralph Lauren
4. Sunglasses

Torrential downpour on British soil leaves little opportunity to don your favourite sunglasses, so take full advantage whilst abroad. It’s the only time you can wear sunglasses all day, every day without any judgement whatsoever. Just refrain from wearing them at night (or even worse, in a nightclub) – that’s just tragic.

As always, Wayfarers and Clubmasters are solid choices, with many cheaper alternatives to the luxury of Ray-Ban. The Keyhole style is also popular this season, adding a 1950s feel to modern menswear in black, brown and tortoise-shell hues. If you’re a rather clumsy sunglasses wearer, it’s probably best to buy a few ‘disposable’ pairs, as there’s always the chance they’ll go missing/get broken very quickly. On the flipside, if you’re a little more militant with sunglasses care, take your best shades and relax with the knowledge of greater quality and proper UV protection.

Your facial shape ultimately dictates what shades suit you personally, so experiment with a few styles to see what works best for you. Be wary though – as sunglasses get larger and squarer, you’re more likely to look like an extra from Jersey Shore, so do be careful when going for the oversized look.

Avoid gold and chrome accents at all costs, unless you’re going for the Vegas bling look, which is a different article altogether! Also worth noting are the bright, vivid colours that have saturated the high street; a sorry reminder of the bygone ‘New Rave’ period, they have no place in the suitcase of any self-respecting modern gent. Same applies for thin, 90s dad-style sunglasses – leave them for the golf course, or better yet… the bin.

  • Topman Navy Blue Round SunglassesTopman Navy Blue Round Sunglasses
  • Asos Wayfarer SunglassesAsos Wayfarer Sunglasses
  • Ray-ban Clubmaster SunglassesRay-ban Clubmaster Sunglasses
  • Gold Caravan SunglassesGold Caravan Sunglasses
  • Uv Protection Tear Drop Frame Aviator SunglassesUv Protection Tear Drop Frame Aviator Sunglasses
  • Tortoishell Coated Keyhole 4170 SunglassesTortoishell Coated Keyhole 4170 Sunglasses
5. Hand Luggage

You want plenty of room for all the aeroplane essentials; iPod, book that never gets read, token duty-free foreign sweets and the largely unnecessary sandwich bag full of potentially dangerous liquids like mouthwash. You’ll want something decent and more importantly, practical. Outside of a business trip, there’s no excuse for a mini trolley case with nothing inside, and unless you’re going backpacking, don’t take a heavy-duty Bear Grylls-esque number complete with carabineers and ten-thousand compartments. It’s not an expedition, it’s just a holiday.

The canvas knapsack is pretty much ideal for hand luggage, spacious without being sizeably offensive. Easy to carry (and easy on the eye), they’re massive on the high street and a great style move with plenty of versatility depending on your outfit. Another route is the scholastic-inspired satchel for a more shapely bag, or try the EastPak/Jansport rucksack or preppy holdall if you’ve got the extra luggage.

I wouldn’t advise a drawstring bag on any occasion whatsoever, and if you’re using a bumbag to be extra safe with the documents, never exhibit or discuss this in public. You’re just exposing yourself to sheer unadulterated ridicule.

  • Asos Leather Old Boy SatchelAsos Leather Old Boy Satchel
  • River Island Canvas BackpackRiver Island Canvas Backpack
  • American Apparel Denim School BagAmerican Apparel Denim School Bag
  • Topman Brown Suede Printed RucksackTopman Brown Suede Printed Rucksack
  • Fred Perry Black Contrast Barrel BagFred Perry Black Contrast Barrel Bag
  • Cheap Monday Shane HoldallCheap Monday Shane Holdall
The Final Word

So, aside from your sun tan lotion, insect repellent and your passport, hopefully you’ve gained a little insight into the rules and regulations surrounding the holiday essentials.

Going abroad is all about plenty of sunshine and plenty of laughs, so you may as well enjoy it whilst looking your best. There’s no reason to pack everything but the kitchen sink; with just a few right decisions, you’ll be a big player in the style stakes, and you’ve got no excuse for a naff pair of sunglasses or comedy Union Jack swimshorts.

Have a great trip (and an even better style survival kit).