On paper, dressing for a beachside vacation seems like a breeze. After all, there’s really not that much clothing involved. In reality, with more skin than fabric on show, what you do choose to throw on takes on added importance.

Swim shorts should be the foundation of your outfit, of course, and a solid pair that fits just right will give you a jolt of confidence. Polo Ralph Lauren is an eternally safe bet – or try a tastefully printed pair by Brunello Cucinelli. From there, toss on a lightweight camp-collar shirt in a bright hue by Incotex, then add a touch of elegance with a grown-up sandal from The Row.

As for accessories? They may, by their nature, be the side players, but they’re especially vital when you’re dressed in little else. A canvas beach bag, sleek sunglasses, some beaded jewellery and a bucket hat will tie everything together nicely.

The ideal city-break outfit will need to tick a lot of boxes. You want something that’s comfy enough for the steps you’re going to be racking up, yet equally polished for when you visit more sophisticated establishments. It’ll need to be compact, too, since we likely won’t be checking in a 30kg suitcase. And, most importantly, you do not want to look like a tourist.

Our advice is to opt for an ultra-elevated spin on what you’d wear back home. For example, you can’t go with wrong with an overshirt or light jacket by Polo Ralph Lauren, a T-shirt by The Row and some wide-leg tailored trousers, paired with sleek – and, crucially, not attention-grabbing – hardware.

A crossbody bag is ideal for obvious reasons. Meanwhile, Jacques Marie Mage sunglasses look good whatever the setting. And finally, chunky-soled loafers from Common Projects will be walkable, but equally won’t get you turned away from the fancy restaurant you booked months in advance.

If a weekend of rambling or a fitness retreat is your idea of a good time, then you won’t need telling that function trumps all else here. What we will say, however, is not to forget the more design-led gear brands who do their job brilliantly, but whose kit you wouldn’t be ashamed to be seen in.

Moncler Grenoble, Satisfy and DISTRICT VISION all come to mind for good-looking Gorpcore with substance. Likewise, Stone Island’s jackets hold up just as well under the elements as they do in the city.

Obviously, your footwear will be the most crucial part of your outfit – and there’s no such thing as being too practical in this department. Fortunately, Mr P. has partnered with techy footwear brand Diemme for a selection of sturdy hiking shoes that don’t disappoint on the style front.

Much like with an activity holiday, you’ll want to come prepared for whatever the weather throws at you when prepping for a festival (especially if that festival takes place in rural Somerset rather than sunny Palm Springs). Pack a robust but comfy pair of New Balance sneakers in a dark hue and you won’t regret it later.

That said, music festivals are the perfect arena to be a little more daring with your style. Odds are, whatever you opt for, there’ll be a guy in a wacky costume next to you who makes you look tame by comparison. Print and colour aren’t just welcome but highly encouraged – try statement T-shirts by Gallery Dept. and patterned shirts by KAPITAL.

And if you’ll be outdoors all hours, make sure a bold cap or bucket hat and a pair of CELINE HOMME sunglasses are as glued to your person as your wristband.

Whatever your reason for staycationing this summer, don’t treat it like a consolation prize. Forget that you’re only a half-hour drive from your home or office – you deserve to ignore all those emails, indulge in the room-service menu and pick out clothes that make this rare time off all the more special.

Comfortable pieces in plush fabrics should be high on the agenda, so turn to The Row for all things simple yet sumptuous. Or try a neutral sweatsuit from Fear of God Essentials. For shoes, we’re fans of Common Projects clogs, or a hiking boot by ROA if you’ll be taking country strolls.

Assuming a spa session is part of the plan, we suggest a pair of trunks that veers more quiet luxury rather than any splashy patterns that’ll throw off the energy. And don’t forget a roomy yet smart holdall – such as Brunello Cucinelli’s canvas pick – with plenty of space for your 500-pager.

Plane, hotel and babysitter all booked for that dreamy destination wedding? Now it’s time to turn your attention to what really matters. (No, not the happy couple.)

Though formal dress codes seem to be slipping these days, we’re firm believers that a wedding-guest outfit should rise to the occasion. That doesn’t have to mean stuffy: unstructured Italian tailoring in a lightweight fabric paired with a breezy shirt is a winning formula. Just be sure to go extra luxe by way of Brioni, Brunello Cucinelli or Canali to compensate for the more relaxed fit and tie-lessness.

Add on a buttery-soft brown loafer by FERRAGAMO, which feels more apt than anything laced up. Then finish things off with a necklace, sunglasses and a sleek leather pouch to seal your best-dressed-attendee trophy.