Because getting dressed for the weather in March, April and even May can be a guessing game, we are starting our list with this perfect workwear-inspired jacket by Japanese brand Kaptain Sunshine. Cut for a relaxed fit, it will layer over a gilet or sweater nicely, but looks stylish over a plain tee as well. Wear it with blue jeans or matching trousers for a springy update to the denim jacket.

Italians are much beloved for their insouciant take on tailoring and Boglioli is making an elegant case for unstructured blazers here. Mismatched separates is an easy way into suiting if you’re looking to evolve your look – and a navy blazer is also the perfect place to start. Crafted from a light wool-blend, the brand’s signature K-Jacket blazer is an understated transitional piece you can wear almost anywhere.

If you’re a default-to-a-blue-button-down type of guy, do we have an upgrade for you. This woven shirt from Bottega Veneta sports a collar, buttons and cuffs like your old-faithful, but is made from a visually interesting, tactile and fluid fabric that drapes just so. You can wear it as you would your other shirts or use it as a jumping off point for some more unusual pieces that make you feel unique.

We’ll spare you the cliches about spring weather and simply present you with this twill jacket from Stone Island. Lightweight and practical, this easy outerwear staple will easily become your most-worn item. Style it however you like, there’s really no going wrong with this.

Talk about “tailoring” and people’s minds turn immediately to double-breasted suits, sharp shirts and formal dress codes. The Row caters to those needs – but what it believes in more fundamentally is the idea that everything you wear could, and should, be made with the same care and attention. So, yes, these Marlon trousers are a simple pair of sandy-brown cotton workwear trousers, but they’re also one of the nicest that you’ll ever slip into.

We’re not saying you only need one T-shirt in your life. That would be weird. But if you were to try, for whatever possible reason, to get by with just one, you would want it to be a classic that goes with many, many outfits yet isn’t as plain as a simple white tee. You’d want it to be warm, for those chillier days, yet breathable when things heat up. I think you’d also want to know it was made from organic cotton, which is more sustainable and longer lasting. You’d want this one from Mr P., is what we’re saying.

LOEWE’s Flamenco bags are easily recognised by their oversized knotted leather drawstrings. Now the same signature touch can be found on a more utilitarian suede messenger satchel. It’s a perfectly practical day bag, but so impeccable is the construction, so soft the leather, we’d only carry a selection of smooth-edged items at all times. Borrow a pen? No can do. How about a golf ball?

If you’re stuck in a sartorial rut, one of the easiest ways to spice things up is to take something you know you love and choose a slightly more directional version. Case in point, these croc-effect leather loafers by footwear god Manolo Blahnik. All the comfort, versatility and reliability of a regular loafer, but with that little extra something to keep your haters sweating.

It’s a tennis shoe that you’re more likely to see in the debenture seats than on Centre Court itself. We’re talking a premium full-grain leather construction with suede detailing, made in Italy by the craftspersons of Brunello Cucinelli. Meaning a lot of effort has gone into a sneaker that will effortlessly go with everything in your wardrobe. So, play around ­– just don’t, you know, play tennis.

We know what you’re thinking. There must be a granny somewhere out there who is rightfully pleased with her handiwork on this seasonal cardigan from New York label Corridor. And there is – only, plot twist, she’s in Peru. OK, so it was actually a multi-generational team in a women-run workshop rather than one abuela who hand-crocheted this piece. But it’s a good yarn (as is this pima cotton).

This jade wool and linen-blend sweater doesn’t say “visvim says relax” in bold letters like that infamous promo tee for the 1980s pop band Frankie Goes To Hollywood. But it doesn’t need to – the dropped shoulders do all the shrugging for you. Wear with nonchalance. And maybe selvedge jeans.

We’re obviously all for the rejuvenating halo effect that a well-chosen new item can have on your wardrobe. But what about the classics? The tried-and-tested faithfuls that you can rely on, no matter what, and are worn in just right. AGOLDE’s Curtis jeans offer an overlap of the Venn diagram. Engineered in a flattering slim-straight cut, with minor distressing for a lived-in feel. And as the days get lighter, perhaps your denim should, too?

A MR PORTER favourite, Jacques Marie Mage’s Enzo style are the perfect contemporary reworking of classic square-frame sunglasses. Named for Mr Enzo Ferrari, they are handcrafted in Japan from lightweight tobacco-brown acetate and feature chunky temples and the brand’s signature metalwork and pins. Cool enough for the beach and smart enough for a suit, too.

What makes the Santos-Dumont one of Cartier’s most enduringly popular designs? Its modest size, wearable by all? Its historical connection to the very first watch the maison created? Its interchangeable straps – tan calf leather or slinky stainless steel – that make it truly versatile? Could it be the 100m water resistance, in-house movement and sapphire crystal that allow for peace of mind despite such elegant styling? We guess we’ll never know.

As we edge closer to summer – and as fashion continues to favour open necks and even bare chests – it’s inevitable that the area between chin and chest will be getting more attention. A simple, slim chain is all you need to add interest and (dare we say it) a little sex appeal. As an added bonus, David Yurman’s silver box chain can be customised with pendants to create a uniquely personal piece.

Please, please, please leave the NYC cap at home for your next outing. So instead of NYC, why not… YMC? The London brand has created a multicoloured striped thick cotton style with a distinctly Balearic feel. We’re envisioning it teamed with a loosely buttoned shirt, a glass of white wine and a sea view. Or, you know, with a hoodie and overcoat when you pop out for coffee and a stroll.

Everyone needs lavishly soft sweats to cosy up in and this hoodie from LEMAIRE is a good candidate. It’s made from a lightweight cotton and linen-blend material that has been cut to a relaxed fit for maximum comfort. You can wear it on rotation dressed down with jeans or dressed up with tailored trousers.

A polo shirt might seem like a simple wardrobe item, but its smart-casual appeal is timeless. If you only ever choose one, make it this polo from TOM FORD. It has a slim-fit silhouette and a ribbed-knit handle, which gives it a subtly textured look. It’s finished with a discreet logo appliqué and rendered in a blue hue that’s perfect for sunny days.

A belt is one of those things you don’t really think about until you desperately need it. Save yourself the sartorial distress and add this Noah leather belt to your accessories wardrobe. The light colour means it’ll freshen up any look and contrast nicely with dark-coloured trousers.