Six scenarios, six solutions.

Exactly 50 years ago this year, the fashion designer Sir Hardy Amies published his now classic style handbook, The ABC of Men’s Fashion, a collection of pithily delivered points of view that touched on everything from sun lamps (a precursor of tanning beds – “their use must be considered a bit caddish”) to trouser cuffs (“you can’t have any”). On shorts, he offered readers the following piece of advice: “Never wear [them], except actually on the beach or on a walking tour.”

Sir Hardy never had the chance of debating with Mr Thom Browne on the merits of knee-length suit trousers, or to opine on Mr Pharrell Williams’ Lanvin “shorts tux” that graced the red carpet at the Oscars this spring. Even though times have changed since the 1980s, when Mr Truman Capote was criticised by a judge in Southampton, New York, for wearing Bermuda shorts in court, many of us still worry we’re going to look like a schoolboy if we show a little leg. As we enter the dog days of summer – when a delightful mass-transit commute can reduce the most carefully curated look to a soggy mess, we’re suggesting a few pairs of shorts for a range of situations. Click through the gallery, above, to learn more.

By showing that swim shorts could be smart enough to wear to a beachside restaurant (and more – the Mr P buying team swear blind that they spotted a pair being worn with a blazer during Milan Fashion Week), the British brand Orlebar Brown literally halved the number of pairs of shorts that men are required to take with them on holiday. Just slip on a terry cloth polo shirt and sandals to make an effortless transition from beach to bar – just make sure that your shorts are dry before you take a seat.

Coachella, Glastonbury… These J.Crew shorts have been the cornerstone of our wardrobe when throbbing bass and perfectly legal, organic stimulants are in ample supply. The patchwork pattern is playful without being outright silly, and they’re an effective all-weather option, working just as well with Birkenstock sandals as they do with Wellington boots.

As our Buying Director Mr Toby Bateman recently pointed out with his easy-on-the-vermouth understatement, “Incotex makes the best trousers on the market, so it seems logical that it also makes the best shorts.” Quite. The same craftsmanship that goes into the Italian brand’s famously high-quality chinos is found in abundance here, from the tailored fit to the neatly turned-up hems. Perfect for weekends, just add a colourful polo shirt, woven leather belt and leather sandals and you’re good to go.

We all know the feeling: the excitement of receiving an invitation to a summer function, followed by WTF befuddlement as you wonder how to interpret “festive”, “smart casual” or our bête noire “cocktail chic”. For an easy solution, match these subtly patterned shorts from Oliver Spencer with a cream linen blazer, white Oxford shirt, a silk and linen tie and a pair of suede tasselled loafers. If the event is celebratory in nature – a low-key wedding, for instance – then finish off the look with a buttonhole flower. There. Problem solved.

Looking forward to a day spent multitasking (OK, nursing a hangover) from home? Too warm to wear your favourite sweatpants? Try solving your #FirstWorldProblems with these comfy loopback-cotton jersey shorts from the Copenhagen brand, NN.07. We suggest channelling the gym-wear-as-streetwear trend and wearing these with adidas pool sliders and tube socks when popping out to the shop.

If you’re lucky enough to work in a suitably laid-back office, and have the confidence (and the legs) to give shorts a go, then we suggest avoiding the fully co-ordinated “shorts suit” look and opting for separates instead. It’s smarter, and will make your commute to work feel less like the school run. These pleated shorts from Wooyoungmi would work well with a cardigan or unstructured blazer in a lighter shade of grey, a crisp white shirt and a pair of Derbies. Keep things sharp – you are at work, after all. Jil Sander is a brand to remember.