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In the 146 years since Levi Strauss riveted together his first pair of jeans, denim trousers have been reworked in every shape, colour and style imaginable. Which makes for a lot of choice. Some are universally flattering. Others are not. There are jeans that you can wear anywhere, and jeans that only work in a handful of very specific looks (denim short-shorts, we’re looking at you). It can be, on the whole, a tad confusing. So we tapped our expert stylists to break down how to wear each of the most popular cuts, from spray-on skinny to tent-like wide fits.

How to wear skinny jeans

What are they? Jeans cut tight. And we mean, really tight. They should cling to your skin, tapering aggressively from the top of your thigh to your ankle. Often, they’ll be slightly stretchy, to make wearing them slightly more comfortable.

Who they suit: Skinny jeans are so unforgiving that it’s astonishing they remain as popular as they are. They tend to work best on equally skinny frames, as bigger thighs especially can make them bunch in weird ways. Rock stars and teenagers can look good in skinny jeans. For everyone else, it’s a struggle.

How to wear them: At the extremes of fit, you need balance. Chunky trainers and boxy tees will throw out your silhouette, so stick to slim everywhere. On your feet, that means things like sleek Chelsea boots or minimalist trainers, while above the belt tailored shirts and figure-hugging jackets always work.

How to wear slim-fit jeans

What are they? The skinny jean’s easy-to-wear cousin. Slim-fit jeans still taper, but less, so there’s a little bit more fabric and every lump and bump isn’t on show.

Who they suit: Pretty much everyone. They create a long, lean silhouette that looks good on men of almost any physique. The only exception is if you’ve got really huge thighs – if you’re a Premier League footballer, or you can deadlift a Nissa Micra, then slim turns back into skinny.

How to wear them: Slim is, by a distance, denim’s most versatile cut. If you get a pair in dark indigo, then you can dress them up with a blazer (Ralph Lauren, king of smart-casual, even adds a shirt and tie) but they’ll still look good with a hoodie for lazy weekends.

How to wear regular-fit jeans

What are they? The original cut, as you might have guessed from the name. These tend to have only a very slight taper, which means they’re much wider at the ankles than the fits above.

Who they suit: The extra fabric means they’re ideal for bigger guys, because you won’t have to squeeze in your thighs and buttocks to make them fit. They’re also good if you tend towards a fairly classic style – this cut’s endured for more than a century, so it won’t be going out of style any time soon.

How to wear them: Regular-fit jeans rarely feel as smart as slimmer variants, which means they’re best worn casually. The originals were designed for workers, and they still look great with other rough-and-tough pieces, like work jackets, check shirts and boots.

How to wear straight-leg jeans

What are they: Jeans with no taper. These drop straight from thigh to ankle, which means they’re roomy and, currently, very on-trend.

Who they suit: These are great for guys with bigger builds, because they balance your top and bottom halves. If you’re slimmer, you can still wear them, but be extra careful about the fit of the rest of your outfit. If you go too big, you’ll disappear inside your clothes.

How to wear them: Straight-leg jeans have a 90s feel (and, before that, a 50s vibe) so they’re perfect with other clothes that nod to that era. Like skinny jeans, we’re nearing the edges of the fit spectrum, so balance is key – think chunkier shoes and looser tees and knits.

How to wear wide-leg jeans

What are they: Fashionable, but not necessarily that functional, these are oversized and tent-like jeans that exist mostly as a middle-finger to the dominance of skinny jeans.

Who they suit: You need to have a bit of heft to pull off jeans like these, otherwise they’ll drown you. Whether your build has been honed by spending hours in the gym, or avoiding the gym, wide-leg jeans can create a nice counterweight to a bigger torso.

How to wear them: They run counter to most things you think you know about jeans. Because of all that extra fabric, they’ll often come with a higher waist-band and pleats, which means they work best worn on your actual waist with a white tee or shirt tucked. You also need shoes with a bit of weight, or they’ll disappear under the hems.

Words: Tom Banham
Photography: Danny Lowe
Styling: Izzy Harvey