Most of us like to think we’ve got this getting dressed thing sussed. We’ve read the runway reports, swotted up on key fashion trends and even coughed up for a Cuban collar or two. Surely that’s enough to be inducted into club menswear?

Not quite. Given that a look is only as good as its weakest link, it’s equally as important to ensure you’re stocked up on the timeless staples that return year after year.

To save you from rummaging through the leftovers of more savvy shoppers, here are 21 always-in-style items to get you ahead of the herd before spring, well, springs.


Ideal for times when it’s neither too warm nor too cool (read: practically every outdoor event between now and June) an overshirt is one of the unsung heroes of menswear. Bought with a roomy but structured cut, it can be layered beneath outerwear now or be worn as your top layer when the intermittent sun makes it time to leave your jacket at home.

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Oxford Shirt

The Oxford shirt has got all-rounder status written all over it. Capable of smartening up jeans in one outfit and dressing down sharp tailoring in the next; if you haven’t got one yet, look for a weighty fabric that’s cut slim and watch in amazement as nailing transitional style gets a whole lot easier.

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White T-Shirt

It may be hard to distinguish one plain white T-shirt from the next at first glance, but pull it onto your torso and the difference becomes immediately clear. When stocking up on this most basic of basics, look for a snug (but not too snug) fit with sleeves that hit around the halfway point on your upper arm and, if your budget allows, opt for soft Supima cotton.

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Grey Sweatshirt

No harm could ever come from owning a classic sweatshirt in every shade. But in the interest of time and money, we’re putting all our eggs firmly in the basket of the original sportswear staple. A grey marl version cut from soft loopback cotton-jersey scores big, particularly when worn with a pair of sand chinos for ultimate Paul Newman vibes.

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Knitted Polo Shirt

Don’t let lads on tour have all the fun. A polo shirt, if approached the right way (chiefly without a stupid nickname stamped on the back and the collar down), can be one of the most perennially stylish items in a man’s wardrobe. For a slice of modern-day Dickie Greenleaf, go long-sleeved, logo-free and choose an open collar without buttons. More peak Riviera, less troublesome tourist.

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Most guys think of chinos as the kind of seasonless wardrobe addition you can make with your eyes closed. But the reality is that the gulf between bad chinos and good chinos is big. Very, very big. Aim for slim, unfussy styles which are sharply tailored and end at your ankle: it’s the difference between looking like smart-casual Ryan Gosling and smart-casual Jeremy Clarkson.

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Mid-Wash Denim

It’s easy to fall into the trap of wearing dark raw denim year-round, given that it’s almost never out of style. To give the prince of darkness thing a rest for spring, try a mid-wash pair. Granted, they may not be able to masquerade as formal trousers in the workplace, but they’ll look pretty sweet when cosied up against spring’s shades of pastels and whites.

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Light Tailored Trousers

Assuming you’re not a ‘freelance creative’ who spends his days working from home in nothing but underwear, chances are you’ve already got a handful of dark tailored trousers at your disposal for the working week. What you perhaps don’t have (but should) are a few lighter pairs – think pale grey or stone, which won’t make your legs feel like they’re trapped in a trousery furnace.

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Unstructured Blazer

There are guys who just ‘get’ tailoring, and there are those who don’t. The unstructured blazer is pretty much the one piece of tailoring that can unite all men thanks to its softer shape and less rigid styling rules. You’ll get your money’s worth out of one, too: dress it up for work with separates or wear with a grandad shirt and jeans for evening smart-casual styling.

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Denim Jacket

The denim jacket’s greatest asset is its ability to slot seamlessly into your existing menswear roster. While it’s still brisk out, master advanced-level layering by slipping one beneath an overcoat, then riff on nineties styling by wearing it over a T-shirt and darker jeans in spring. Opt for a classic design with minimal embellishments, and you’ve got a friend for life.

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Field Jacket

While trends come and go, no matter the season (or year) you can always bet good money on military menswear. Unlike brass-buttoned peacoats that are still a little too indie rocker circa 2007, a field jacket has a knack for always feeling current and will play nice with as many or as few layers as you need.

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Harrington Jacket

Make no bones about it, the Harrington jacket is one of menswear’s greatest ever players. The key to its timeless style lies in the fact that it’s simple, unfussy and (shock) particularly good at keeping cold breezes at bay. Even if you tire of yours in a few seasons (though we doubt you will) you can always pick back up where you left off years down the line.

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Chukka Boots

In a world of strait-laced shoes and chilled-out trainers, chukka boots happily occupy the middle ground. Being neither too dressy nor informal, a trustier footwear companion you couldn’t find. You’ll need to wear them with jeans or chinos now, but when (or rather, if) things hot up, they’ll look equally handsome with a pair of shorts.

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Leather Penny Loafers

If there was ever a piece that sums up iconic preppy style, it’s the penny loafer. Of course, with spring comes showers, so whether you recruit a pair for a high-low look alongside jeans and a logo T-shirt, or to foot tailored separates, sidestep suede in favour of durable leather.

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White Sneakers

White sneakers often go from box-fresh to a bit grubby to a bloody mess over time. Like a fractured relationship, it’s easy not to notice things have gone awry until it’s way too late. Whether you go iconic with Stan Smiths, sporty with Reebok Classics or fancy yourself as a stealth wealth Common Projects kind of guy, make sure yours are always fresher than wet paint.


Nato Strap Watch

Modelled after the robust styles used by the British military, a Nato fabric strap is the obvious choice when shopping for a hardy timepiece. Go woven with your wristwear for spring and not only will you climb the style ranks, you’ll also avoid the sweaty wrist that comes from leather and steel come summer.

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Leather Holdall

There are few ways to cart your kit from work to a weekend away that are more stylish than a classic leather holdall. Invest in a sleek design now (black or brown is best) and you will look the business, even if you’re not flying business.

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Baseball Cap

The days of the baseball cap being a signifier of the slovenly are well and truly over. Menswear-approved designs rendered in tactile fabrics have smartened up this sports-inspired head topper, and the results are impressive. Looks aside, they’ll also stop you forcibly squinting at the sun on days when you forget your sunglasses. Win-win.

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Casual Belt

When it comes to style, anything that aids an easy life gets an enthusiastic thumbs up from us. Therefore, buckle up in a casual belt this spring. Bought in black, brown or navy, they are smart enough to wear with a grandad shirt and chinos in business-casual offices, and won’t give your jeans the gaudy buckle treatment on the weekend. If you want to get all of the feels, choose a woven or plaited design.

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Slim Cardholder

Between contactless cards and smartwatches, it’s not hard to see physical money going the way of the dodo. Stop lugging around a beast of a wallet stuffed with receipts and drag yourself into the 21st century (while keeping the lines of your trousers intact) with a slim cardholder.

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For what are essentially small (but often perfectly formed) bits of plastic and metal joined together, sunglasses are pretty pricey. To get favourable cost-per-wear calculations, don’t wait until summer to invest through fear of looking like a poser. Your eyes (and your wallet) will thank you.

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