Most guys’ summer calendars are light on engagements on the Buckingham Palace lawn, and most are still waiting on that invite to the Gold Cup polo tournament. But damp barbeques, day-to-night drinking sessions and other such inevitable scenarios? Booked solid until September, thanks.

And just because these events don’t require a swish hat, unless you are that way inclined, each does have its own approach when getting dressed. Here’s how to boss any social engagement with the five essential summer outfits you’ll need this season.

The Heatwave When You Still Have To Go To Work

Most guys lust for sun, until it actually arrives. Then we rediscover a universal inability to handle heat. Train tracks warp, headlines scream that it’s hotter than Dubai, and people everywhere shed clothes like they’re lined with napalm. But a glimpse of nipple won’t be welcomed at the morning sales meeting.

You have two weapons at your disposal in the fight to stay cool and decent: fit and fabric. Skinny- and slim-cut clothes trap warm air against your already sweaty skin. Loosen up, and it starts to flow. “A boxy shirt will keep you cool on those hotter than hot days,” says ASOS head of menswear design Nick Eley. This shape is already off dress code, so don’t push it any further with hula girl patterns – plain white, light blue or grey designs reflect heat and the wrath of HR.

Whichever material you choose should be just as breezy. Linen and light cotton are both covered with tiny holes, which ensures the air circulates. “Linen is a great option in tailoring or for granddad collar shirts,” says Mr Porter style director Olie Arnold. “Lightweight chinos are also office-worthy.” If shorts definitely aren’t, then a slight roll gets some ankle skin on show, to help your body dump heat. And won’t get you handed a P45.

The Wedding With The Vague Dress Code

Weddings used to be simple. If the sun was up, you wore tails. Once it dropped, black tie. But dress codes have mutated in recent decades. Today’s couples demand things like ‘rural chic’, ‘city formal’, or just ‘fabulous’ – a request so ‘WTF’ it could mean a suit or short shorts.

So how do you make sure you’re not the only guy with his thighs out? You fix up, look sharp, of course. “You want to be smart, but not as smart as the groom,” says stylist Kitty Cowell, who has worked on campaigns for the likes of Nike, ASOS and Universal Records.

The safest bet is tailoring, with removable trimmings. That doesn’t mean the outfit you wear to work; after all, the shade should be celebratory. “Wear separates rather than a full suit,” advises Arnold. Neutral combinations – think navy with beige, grey with blue or white with charcoal – will work in any pictures, whether the wedding party is in tails or tees. The shirt should be plain, with a classic point or button-down collar. Then if you’re the only guy who turns up in a tie, you can pocket it.

On which note, your breast pocket should pack a bright silk square that complements your jacket – yellow or pink is suitably nuptial. If it turns out even that’s too much, you can move it to another hidden pocket.

Finally, shoes. “A monk-strap is more interesting and will work both smart and casual,” says Arnold. If you do need to take your look down yet another peg, nip to the bathroom and ditch the socks.

The Lunchtime Drink That Finishes At Breakfast

It always starts with the best intentions. A quick pint, a catch-up, then home to mow the lawn. But it’s so nice out, the first sun we’ve had in ages. One more, for the road? Well, you can’t leave before the rounds are level. Dark comes, as do shots, and suddenly you’re Googling local fry-ups.

The accidental night out involves moving from day to night, hot to cold, beer garden to, potentially, nightclub. The best way to cope with all six scenarios is layers – and a bag to stow them in. A grown-up leather tote or backpack won’t annoy bouncers and can stand up to grass – and the cloakroom – without you stressing stains.

Your footwear needs to toe the same line. A pair of sleek, minimal leather sneakers are comfortable enough for an all-dayer and will pass the dress code test (leather also wipes clean, just in case). “Team them with simple black jeans, a white T-shirt and a leather biker jacket,” says Cowell. In your bag, stow a post-club hoodie and a portable phone charger. Or spend eternity trying to flag down a cab.

The Barbecue Where It’s Guaranteed To Rain

What is summer without an al fresco party that plays out beneath grey skies while people shield their drinks from drizzle and you shiver in shorts?

Pragmatism (i.e. checking a weather app now and then) beats dressing for the day you hope will happen. But you can still keep your (beer) glass half full. “Even if it’s not 35 degrees outside, it’s nice to pretend with a printed shirt,” says Arnold. A Cuban collar shirt has long been the favourite of uncles who don’t know their limits. But stick to this season’s new slim-fit takes, in muted tones, and your nod to tropical weather comes across as smart, not ‘zany’.

To outflank the inevitable, top this with something waterproof. Your prudence might upset the host, so you need outerwear that doesn’t look like you expect torrents. “Lightweight coats are practical, but still look cool,” says Cowell. A showerproof shell (think a bomber jacket or blouson cut from a non-absorbant twill) is a fuss-free throwover that won’t cause you to overheat. Just in case.

The Birthday Drinks Your Ex Will Be At

You’ve split your DVDs. Argued about who gets the dog. But your social circle doesn’t divvy up as easily.

School friends are simple. Ditto colleagues. But there’s equal claim on your college mates. And if your erstwhile other half won’t back down, why should you? So now you’re about to meet for the first time since the tears, and you need to look good. Like, see-what-you’re-missing good. But you can’t let anyone know you made an effort.

Before you think about clothes, turn your attention to what they go on. (In a pinch, the full body prison workout should be enough to stir the heartstrings.) Then look for clothes that say you’re doing just fine, thanks, without labouring the point. If you debut something dramatically different to your usual style, people will assume you’re struggling with a post-breakup reinvention.

Instead, opt for the best basics you can afford: a blazer that you’ve had tailored; slim-fit jeans cuffed just so; a Henley shirt that showcases your new bench press PB; a haircut from a high-quality barber.

Great materials and the perfect fit mean no one will be able to put their finger on why, but you know what, you’re looking just great, especially considering, you know. Then accessorise with a smile – and ignore your ex’s glances.