A button-down is what you can confidently call an unassailable menswear classic without sounding like you spend all your time on the malefashionadvice subreddit (hey, no judgement here). Which is why it’s at the top of this list. Originating as a solution for polo players whose collars flapped in the wind, it’s become something of a sartorial main character that you can layer under a blazer to a meeting, or style it untucked with chinos or denim on the weekend. White and sky blue are the easiest go-tos in terms of colour, and will realistically yield the most wear, and while they come in all kinds of fabrics, an Oxford cloth button-down – known as the OCBD among menswear nerds, ahem – is arguably the most classic and versatile.

Striped shirts inject some personality into an outfit without being overwhelming, making them an easy way to experiment with pattern and colour. Vertical stripes also create a visual elongation, making you look the tiniest bit taller. Look for narrow pinstripes for a refined office-appropriate look, or bold, wider stripes (sometimes known as butcher’s stripes because they recall the stripes used on a butcher’s apron) to add more flair to a get-up.

Despite its broad-ranging associations – from lumberjacks to 1990s grunge and 2010s hipsters – the flannel shirt is singular in its ability to add a rugged cool to your off-duty looks. In fact, a flannel shirt can be one of the most reliable pieces in your wardrobe, especially in the cooler months. Japanese brands are particularly good at making them: look to Beams Plus for some great flannels that blend that vintage American-workwear vibe with some contemporary polish. Or try Cherry Los Angeles’ modern take. Styling-wise, they often look best when worn unbuttoned over a casual tee as an overshirt, and with equally rugged trousers, such as blue denim jeans or cargo pants.

If you’re about to embark on some winter sun, dressing well in warm weather after battling the elements these past few months can feel jarring. A cool linen shirt, however, is something you can look forward to switching your favourite knitwear for. Pair it with tailored shorts, linen trousers, or swim trunks – it’s difficult to go wrong. Lightweight, breathable and still elegant after being crumpled in your hand luggage, a linen shirt will look the part whether you’re on a Mediterranean terrace or spending a day at sea. The Italians make some of the best ones (of course they do) – look to ZEGNA, Etro and Lardini for some reliable examples.

Denim’s softer cousin, the chambray shirt can be a real wardrobe workhorse. Carrying the rugged charm of denim without the heft, it’s versatile enough to be worn under a winter sweater when it’s colder (the textures look great together), but will work just as well on its own. Officine Générale is a reliable go-to for chambray – the French brand makes its styles using Lyocell, which is extra-lightweight. One more styling tip: if you’re feeling adventurous and want to channel your inner cowboy, a chambray shirt looks great when paired with a bandana tied around your neck. Yeehaw, etc.