We have some simple advice for getting dressed this summer and it comes from a rather unlikely source: The Very Hungry Caterpillar. Allow us to elaborate. Breaking free from the shackles of your sofa and out of your comfy cocoon, we invite you to spread your sartorial wings (spoiler warning: he becomes a butterfly at the end) and exercise some out-of-the-box thinking when it comes to putting your warm-weather outfits together.

Now, we should be clear: no one is saying you must go full Mr Harry Styles at the Grammys and rush out to purchase a pistachio feather boa. But braving a more daring approach to your personal style will set the tone for the summer ahead. One in which, we hope, you’ll be making up for lost time. Here, then, are 20 bold pieces that will help you make your grand reentrance this summer.

Who likes short shorts? Well, we like short shorts, as does, evidently, The Elder Statesman, alongside a long list of well-dressed celebrities who have had a leg up on the trend for a while now (see here for further details). This pair is knitted, which, yes, does mean you run the risk of having them mistaken for one of your various lockdown “projects”, but surely that only adds to the charm?

We’ve long been drawn in by the allure of pastels, and have spent a good deal of time extolling their virtues of late. Not as bold as neon, mind, but just as eye-catching, they’re also intrinsically summery. As, naturally, are bucket hats ­– consider this Polo Ralph Lauren number your ticket to the pool-side bar, beach or a festival. Or, you know, at the very least, pretending you’re there.

Logo tees themselves are nothing new. Even those who would file their style under “classic” have subscribed, at least in small measure, to the trend. Fendi however, as fans of the brand will be aware, is not known for doing things in small measure. Pattered with the designer’s iconic monogram, this T-shirt will attract all the right kind of attention. If you want to take it to another level – and if you’ve read thus far, let’s assume you very much do – there’s a pair of trousers to match.

These Valentino sneakers made their debut as part of the label’s hit SS21 show. Crafted from intricate macrame, one of the brand’s historical signatures ICYMI, they’re truly one of the most singular silhouettes on the market right now. And considering the state of current sneaker trends, which include everything from self-lacing marvels to bulbous, Frankenstein’s monster-like hybrid styles, that’s surely saying something.

Let’s not beat around the bush – this item, billed as a messenger, looks a lot like a handbag. Not a clutch, since it has a strap, but with echoes of purse, certainly. We get it, it’s even pink. Now, we could point to the fact that the demarcations between genders are crumbling and, given that you’re currently carting around a wallet, phone, keys, hand sanitiser and face mask in your bulging trouser pockets, it would actually come in handy. The truth of the matter is that it takes a big man to carry such a small bag. So, you have to ask yourself: are you that man?

The chief takeaway from The Great, the recent (and excellent) comedy-drama series that plays fast and loose with Russian history, is that Peter III was a massive tool. Still, emperor knew how to dress, hence you saw him in pearls first, some 250 years before A$AP Rocky raided his grandmother’s coffers. Undercover’s take on the trend contains two strands of pearls linked with silver chains, which can be detached and worn as separate pieces. Plus, note the very SEX-era Ms Vivienne Westwood razorblade pendant, of which Peter, not a man known for his tolerance of beards, would no doubt approve.

Any seasoned partygoer knows that it’s not just your outfit that leaves an impression, it’s also the scent you choose. TOM FORD’s Metallique fragrance, which is infused with a heady mix of pink peppercorn, sandalwood and ambrette seed, it makes a sophisticated statement that won’t overwhelm. Olfactory magic.

We all know someone – let’s call him Nigel; he’s a whiz with a spreadsheet – who likes to rock a novelty sock. Sure, the rest of him is trussed up in an ill-fitting suit, but his ankle is where the fun is at, right? Sacai’s patchwork socks are not for him. Rather than an afterthought, socks should be the foundations to build an outfit around, and this pair urge the wearer to go wild with the rest of their ensemble. Part Prince, part Ms Carole Baskin, this is where a wardrobe adventure should begin.

Before we get to the 15BM04 calibre hand-wound movement, with seven-day power reserve, on this ornate stainless steel watch by Bovet, it should be noted that the mechanical watch itself is something of an antiquity. Long before smartphones rocked up, the quartz revolution had rendered such items old hat. So, it’s worth remembering that the chief application of a wristwatch today is not to tell the time, but to look the part. Which is where this Fleurier chronograph, inspired by a deep dive into the Swiss watchmaker’s archives, excels. The act winding it makes it a ritual, too.

As far as making a grand entrance goes, it helps if no one else is wearing the same thing as you. The USP of these iggy T-shirts is that no two are the same, with each one having an individual collage of posters, adverts and graffiti.

Part of being well-dressed is knowing how to standout without trying too hard, and this printed shirt from Dries Van Noten strikes just the right balance. Cut from lightweight cotton and adorned with mother of pearl buttons, it’s just the thing for a breezy summer’s evening.

After what seems like an aeon spent indoors, nothing beats the thrill of leaving the house in a pair of sunglasses. It really makes you feel like you’re going somewhere, even if that somewhere is just the shop on the corner. These chunky acetate frames from Jacques Marie Mage are stylish enough to impress the people behind the till, in any case.

Wondering how to put your best foot forward this season? A pair of Birkenstock’s Terra sandals may be a step in the right direction. Designed by Belgian deconstruction specialist Ms Saskia Lenaerts, and here realised in striking hues of black and blue, this is footwear to make a splash in this summer.

We’re willing to wager the opportunities for soaking up the sun have been limited of late. But that doesn’t mean you can’t go back into the world without a healthy glow. These self-tanning wipes from skincare whiz Dr. Dennis Gross will help you achieve just that, while a dose of vitamins and alpha and beta-hydroxy acids will restore dull skin to its former glory.

Down jackets are, by their nature, usually quite big. If, then, you add large blocks of colour to the mix, as Mr JW Anderson has done with his collaboration with Moncler Genius, the result is outerwear that makes a really bold statement. This Bickling style quilted shell down jacket is functional, fun and certain to make an outsized impression.

If you’re too attached to sweatpants to leave yours at home, then we can’t really blame you. Now, though, is the time to upgrade the format as you reenter civilisation. Try turning them into a talking point. These patchwork sweatpants by AMIRI, which are tie-dyed with soft blue and purple hues, fit the bill. They’re a statement to be sure, but infused with the brand’s laid-back California cool, an easy one to make.

One of Paris’ best-known tourist traditions came to an abrupt end in 2015 when authorities removed the thousands of padlocks, left by couples from around the world, attached to the railings of Pont des Arts. But while the “love locks” are long gone, their symbolism remains, and is celebrated here by Givenchy, itself something of a Parisian legend. The gold-tone padlock adds a romantic touch to these outstanding croc-effect Chelsea boots.

With its old-school hiking vibes, teddy-bear textures and riotous colours, not to mention geometric patterns that wouldn’t look out of place on the upholstery of the 159 bus, this fleece jacket from streetwear brand Aries is guaranteed to turn heads when you enter a room. But it’s the finer details, such as the red piping and hiking-lace zip pulls, that’ll keep them looking.

If a tuxedo jacket could ever be described as “relaxed”, it would be this one. It comes courtesy of Giuliva Heritage, the ready-to-wear line of Italian tailor Mr Gerardo Cavaliere, and has the look and feel of something your grandfather might have worn – if your grandfather was a dapper Neapolitan gentleman. With its double-breasted construction and extraordinary, wing-like satin lapels, it’s is a timeless piece of tailoring and the sort of garment we’ll be actively seeking out excuses to wear this summer.

The past 12 months saw us adopting a more, how can we put this, domestic way of life, with comfort firmly back on the style agenda. Now that we’re ready to set foot in public again, this isn’t going anywhere. And besides, who says that comfort and dressiness can’t go hand in hand? Certainly not Bottega Veneta, whose jacquard trousers, in an almost snakeskin-like material called “bubble bouclé”, do both very well indeed. If you really feel like pushing the boat out, there’s a matching cardigan, too.