Five holiday style misses - and how to avoid them 

Ray Winstone in Sexy Beast
Ray Winstone in Sexy Beast

While no one likes a dictatorial approach to dressing, summer holidays are a curious grey area when it comes to a man’s wardrobe. Most of us spend our working lives in standard issue uniforms, so the minute all bets - and workaday duties - are off we can feel somewhat adrift, stylistically speaking. And thus, from Marbella to Morocco, a trope of somewhat questionable attire gets trotted out. 

Armani spring/summer 2019

I am of the opinion that if you enjoy wearing something, go for it, but the offending items below might be best relegated to specific situations - cargo shorts for actual active service, for example - rather than accompany you on precious out-of-office time.


Absolutely fine for David Gandy posing off the coast of Capri in a Dolce & Gabbana advert and the swaggeringly macho on Ray Winstone in Sexy Beast, but somewhat problematic for the rest of us. 

Bulldog deep sea trunks, £225; Orlebar Brown

The issue is that Speedos’ shrunken proportions cut severely under the waist line, meaning that if you’re anything but trim you’ll end up with a certain degree of overhang. Not to mention how, ahem, forthright they are with your goods on display. 

Instead, opt for swim trunks that are tailored - British brand Orlebar Brown makes trunks with side fastenings to ape the effect of smart trousers - and cut off mid thigh. A sleek pair in a discreet print will work harmoniously in a lunch setting, particularly if they’re made in a quick dry fabric. No one wants to see a pair of budgie smugglers as they sip their rosé.

Bucket hats

Men’s fashion would advise that this 90s headgear is back, but tread with caution. The rule of thumb is that if you’re old enough to remember wearing them during your raver days, it’s best to leave them there, alongside the Smiley face emblems and shell necklaces. 

Panama hat, £49; Cordings

Allow the millennials to discover them afresh for trips to Wilderness and instead opt for a pin-sharp, straw Panama; it’s far more sophisticated, and breathable too.


Football T-shirts; fine for the terraces, less so on a Santorini terrace watching the golden sunset. By all means, don your colours with pride when you’re enjoying the beautiful game, but relegate your team when it’s time to step out on holiday. 

Cotton T-shirt, £70; Sunspel

Sunspel is the maker of just about the best T-shirts you can buy, all handmade in Derby using excellent cotton. Yes, they are more expensive, but you’ll wear them endlessly and the price is vastly less than an away kit.

Cargo shorts

Khaki coloured, sagging and evoking all the panache of a Duke of Edinburgh award leader on an excursion through the Peak District, these items are prolific amongst holiday goers who are strangely apologetic about wearing actual shorts, opting instead for ones with a ‘functional’ aspect. 

Seersucker shorts, £30; Reiss

The issue with cargo shorts is that extraneous pockets add bulk, and the cut-off at the knee is unflattering. Instead, choose a pair that tapers to just above knee-height, in a sleek, tailored fit; seersucker fabric will also be more breathable and airy.


This most controversial of footwear gets a bad rep. Certain circles of the fashion elite have reclaimed the socks-and-sandals territory, but this is a tricky combination. 

Alex sandals, £195; Alvaro

Like cargo shorts, men veer towards the idea of functional sandals, which has given rise to a host of climbing and activewear varieties that look as if you’re set to tackle Snowdonia when you’re actually sipping on Sangria. Which is a shame, as specialist brands such as Alvaro and Goya create artfully-crafted, leather variants that are grown-up elder brothers to these sporty, rather ugly looking siblings. ​