What is it about the summer holiday season that sets usually style-conscious men off into a bad decision-making frenzy? Robert O’Connor attempts to point you in the direction of playing it safe yet stylish when you reach your vacation destination this year.

SIN: Board Shorts

Listen up bro, the frat party is over – and the poolside is no place for your elongated, ill-fitting, probably Hawaiian-print half pants. Bruce Jenner and Barack Obama may have been photographed wearing the ‘90s American nightmare recently, but you’ve seriously got to let the elasticated waistbands go for good.

SOLUTION: Matte & Knee-Length

Let’s start with the important stuff first – the length has got to be right, which is one or two inches above the knee. Colour-blocking is kind of a big deal right now so you can get away with major primary colours, but stick to matte fabrics, men should never be shiny – anywhere. Much like with full-length trousers and jeans, the trend is moving towards a slimmer silhouette with little in the way of excess fabric. If you have the quads of a rugby prop, avoid pleats or turn-ups and no matter how much they’re trending, steer clear of short shorts as worn by Cristiano Ronaldo at all times.

SIN: Short-Sleeved Shirts

High street brands like Topman and River Island are trying to make short-sleeved shirts happen for men again – but the memory of men in bad ’80s movies with boxy shouldered short-sleeved ensembles is just too striking a flashback to make the mistake again. Stop trying to make short sleeves shirts happen!

SOLUTION: Roll-up Your Button-Down

Take your queue from TV shows like Revenge and channel the Hamptons, opting for a classic Oxford button-down shirt in cotton – pastel colours are in vogue at the moment, or if you fancy yourself as a bit of a hipster, you can pull off some checked patterns, just do yourself a favour and don’t be that guy who closes the top button. The fit should be relaxed – Gant and Ralph Lauren at the top end of the market know how it’s done, while Massimo Dutti is leading the pack on the high street. Roll the sleeves up and bask in the knowledge that you don’t look like a corporate klutz on a clammy day.

SIN: Offensive Footwear

If you still have to be told that socks with sandals is enough to warrant an arrest from the fashion police, you might need more serious style assistance, but there are a whole multitude of footwear sins beyond this that are downright offensive. The rubber flip-flop is practically unavoidable at some point on your summer holiday, but retire them before dinnertime – as well as being unsightly, try walking home ten margaritas later in those traumatising toe-huggers. Beware: wear Crocs and you may never have sex again.

SOLUTION: Todds & Topsiders

Slip-on loafers such as those made by Todds are a comfortable classic choice. You can  play it safe with neutral tones like taupe, tan, black or navy, or be adventurous with shocking primaries like blues, reds and yellows  – this is one area where you can be as versatile as you wish. You can also get away with wearing topsiders despite not owning a boat, if you have the nautical persona to match, even better. If you’re set on joining the sandal brigade, there is no other choice except for antiqued leather – tan or brown and in crossover design. If you look like you’re going for a hike, you’re doing it wrong. And remember, half socks have never been socially acceptable, and they never will be.

SIN: Product Implosion

Unless you want to be wearing your hair gel on your face by brunch, skip heavy styling products. It’s also wise to change-up your cologne when you’re in a hotter climate, because as the temperature rises your fragrance will diffuse quicker resulting in an overwhelmingly strong scent. Fake tan on holiday should be left to the cast of Jersey Shore or similar style-impaired reality shows.

SOLUTION: Be a Man & Get Your Musk On

Choose a lighter leave-in conditioner by day, and go dry by night. If you can’t handle the unkempt look, sea-salt spray is a new craze that allows your style to stay in place without going hard as a rock. If you’ve got a buzz-cut or you’re thinning on top, be sure to prevent your scalp from being scalded with appropriate SPF 50. For fragrances, light zesty options like Tom Ford’s Neroli Portofino Eau Fraiche body splash allow you to be naughty without making your holiday romance feel nauseous. Scents based on masculine musks are a good way to go for evening and beyond.

SIN: Speedos on Non-Models

Unless you’ve just flown in from Fashion Week, have the body fat percentage of a Jil Sander model – or you’re actual Tom Daley – the chances are you’re not going to be able to pull off the elusive Speedo look. Don’t feel bad, I just wouldn’t want to see you ruin your first impression at the pool and for the rest of your trip be known as that guy with the back fat.

SOLUTION: Junk In Your Trunks

Get in the market for trunks that end mid-thigh. The good news is, since they’re short on fabric, you can afford to go a little wilder with print than you would with your off-beach shorts – just don’t go getting carried away and end up looking like a luminous paisley hot mess. The leaders of Spanish style, Zara, have a strong selection, or if you’re more of the Swedish inclination, H&M is pretty good at getting the runway look on the racks in a matter of weeks too. If you want your product to be reassuringly expensive, Jack Wills has a way of emptying your wallet and filling your ego.

SIN: Thanks But  No Tanks

There are many types of guys who wear tank tops – from the gym meatheads to the hipsters with ironic catchphrases emblazoned upon them – and while I’m giving the bronzed bodybuilders a pass on this one to show off all their hard work in the weights room, there is a better, more flattering option for everyone else. If you don’t have decent arms to showcase, you’re going to wind up looking like an overgrown child in an undershirt. Please Note: This rule does not apply to Channing Tatum and Vin Diesel.

SOLUTION:

A V-neck T-shirt in a superfine cotton will show off your best assets while still retaining some mystery, American Apparel and Reiss have nailed the fit on these. If you want to complete your Hampton look, no-one in the history of the world ever made a misstep in a polo shirt. Badges and heavy branding should be left to the under 25’s or those who could feasibly look like a college student, but it doesn’t mean you have to be boring either – Hackett are experts in colourful and cleverly-detailed polo shirts that will bring you from the dinner table to the cocktail bar in suave Wolf of Wall Street-style moment.