The rigorous rules to relaxed dressing, according to Picky Nicky

At a talk on timepieces organised by Mr Porter, when asked about watch-wardrobe malfunctions, the panel of experts agreed the biggest faux pas was wearing the wrong watch on the beach. I have actually had Orlebar Brown make my husband Álvaro a pair of white ‘Setter’ shorts with gold-hued buckles to coordinate with his Rolex, but must admit my ‘Cape Cod’ watch from Hermès has a Martin Margiela-era brushed leather strap – unforgiving of suntan lotion and salt water – so I’ve never worn it on the beach. That same night I spotted Cartier’s new ‘Santos’ and later treated myself to one. In 18ct yellow gold and stainless steel, it is water-resistant to 100m and looks good with a tan – definitely a beach-appropriate watch.

In my view, the problem of what to wear on or near the beach is not so much the watch but the wardrobe. Some men really struggle at dressing for time off, especially those who hide under a uniform of suit and shirt five days a week. So here are Picky Nicky’s vacation dressing guidelines.

Swim shorts are one of the few places a guy can wear print, but make sure they have a slim, tailored fit. If you wear swim briefs, please put shorts on for lunch.

Appropriate dresser hotspot 1: Test your holiday wardrobe at Il San Pietro. Perched above the sea in Positano, Italy, it’s a family-run jewel of a hotel where smart informality rules. ilsanpietro.it. Illustrator: Danae Diaz

A work shirt is not suitable out of office. Choose something with a softer interlining in the collar. Polo shirts are good but keep the collar down. On a simple round- or V-necked T-shirt, avoid visible branding or you’ll look like the mug that paid $400 for a white tee – and sleeveless is only OK for working out or taking a run.

Knitwear should be cashmere or superfine merino wool, plain not patterned, in camel, heather grey or navy; a sweatshirt-neck detail adds a relaxed touch. And it’s always useful to have a jacket where casual formality may be required in a restaurant – choose a plain blue blazer or a slim-fit blouson.

Shorts should be cut from cotton and finish above the knee. Linen tailoring of any kind is to be avoided unless you want to look like an extra from a period drama or a Pitti Uomo peacock. Jeans (without fake rips) and cotton trousers in plain colours are a good look worn with a slim belt. Stay away from logoed buckles, which suggest an 18-year-old who saved up his pocket money for his first designer splash.

Sandals are cool and comfortable – again, avoid logos. Loafers are better than driving shoes and there is a big difference between leather sneakers (OK) and trainers with chunky moulded soles and tricky colour combinations (not OK). A nude ankle is best in summer, so a note on secret socks: they are meant to be secret – if they’re in any way visible, do without.

Appropriate dresser hotspot 2: At the Hotel Il Pellicano in Italy’s Porto Ercole, almost all the guests would pass the Picky Nicky wardrobe test. hotelilpellicano.com. Illustrator: Danae Diaz

Find the perfect holiday wardobe

Swimwear
Orlebar Brown. Prada does a good nylon short and fun seasonal prints. If you’re fit and wear swim briefs, Charlie by Matthew Zink

Shirts
Aspesi, Officine Générale, Tomas Maier

Polos
Always Lacoste, and look out for its artist-designed Holiday Collector series

T-shirts
Margaret Howell and Sunspel

Trousers and jeans
Officine Générale, Acne, Aspesi and Department 5

Knitwear
Loro Piana and Ermenegildo Zegna

Shorts
Orlebar Brown, Aspesi, Officine Générale

Blazers
Ermenegildo Zegna and Hermès

Blousons in leather or suede
Giorgio Armani, Ermenegildo Zegna and Officine Générale

Sandals
A good selection at Mr Porter, Matches Fashion, Browns Fashion. Álvaro aside, try Birckenstock’s ‘Arizona’ reworked by Rick Owens

Sneakers
Go for a low-top leather ‘tennis’ style, plain in single-colour leather; try Pierre Hardy, Anya Hindmarch and Common Projects

Loafers
Berluti’s soft leather ‘Lorenzo Lecco’, or try a fold-down back from Gucci or JM Weston.