Top 7 Clothing Styles All Stylish Gentlemen Should Own

Who’s wearing the pants? You do. But do you wear the full range of pants, or do you get stuck in a legwear rut? There is a whole world of trouser styles. It’s time to cover your lower extremities in style.


Sometimes called chinos, but better called khakis after their original color. This trouser style originated in the US Navy — worn by officers for service in the warm Pacific climates — but was quickly picked up by civilians and went on to become a cornerstone of the preppy style after World War II.

A chunky, smarter alternative to denim, while still providing a casual look, khaki don’t just come in the dark shade implied by the name, even if it’s the classic color. They don’t just come in the traditional straight leg cut, either. Wear them rolled up with boots in the winter and minimalist sneakers or loafers in the summer. When in doubt, chinos can (and will) suit most occasions.


As often cast aside as more fuddy-duddy than fashion, corduroy (from cord du roi, because it was once woven for kings) is cooler than it looks at first glance. For example, it’s heavy — the stuff of good work clothes before denim took over — and ages beautifully. It softens a suit – literally and figuratively – when it is made to measure. But in trousers it is the ideal line between smart and casual, especially well combined with plain shirts and knitwear; that is, when this shiny fabric gets to be the star of the show.

It’s available in a wide thick wale (that’s the width of the raised portion of what’s basically cut velvet) or a thinner needled cord, which works best in a jeans cut.

wool pants

Wool trousers used to be used only as part of a suit. In more recent years, men have learned to wear smart separates for a style that is relaxed yet formal enough to function in most workplaces or on a chic night out. In recent years, sleek styles have been seen with all-white sneakers, but of course they look just as good with a chunky pair of brogues or Derby shoes.

Because wool pants on their own don’t have much to shout about, a good fit is critical: avoid anything that hugs your legs at any point, but keep the silhouette finish to medium. Always wear nice socks.

Higher waist

A higher waist (the distance between the waistline and the crotch) on pants is without a doubt easier to swing than a low waist. But moderation is advised. If the rise is too high, it will be difficult to get on your bike. Likewise, if the rise is too low and everyone can enjoy the view of your new pants/butt rip. Neither is great. There is, however, an elegance to a high-waisted cut, provided the trousers have a gentle taper. This prevents an abundance of dust from getting in the way.

As with wider pants (see below), a more fitted top half looks best, especially when tucked in – the sophistication of a higher waist is lost if no one can see it, so don’t wear your pants with a non- tucked in shirt. Tucked in is best.


Pleats are a detail that somehow became associated with the older man, with bygone styles. But pleats not only give trouser tops a fullness that’s more comfortable—one reason they’ve oddly fallen out of favor—but they also fit the fuller (that is, normal) figure better.

There’s no need to go overboard – one or two deep pleats will do, or much smaller pleats if you’re going for more. As with high-waisted pants, anything you wear with this style should have the pleats showing, so tuck yourself in or make sure your t-shirt or knitwear sits neatly on the belt.

wide leg

After what seems like an eternity where the skinny-legged pants reigned supreme – worn by everyone, regardless of the fact that it’s only suitable for skinny men – it’s easy to forget that pants actually come in other widths. The wider legs create a completely different silhouette, which also works best with a fitted or form-fitting top that emphasizes the looser cut below. Unlike a slim silhouette, wider legs don’t need to be worn cropped, so make sure they’re tailored to the ideal length.

Buy your pair in a denser, heavier fabric and they’ll drape better, too. Note that a wider leg – the cut from Hollywood’s golden age – will flatter most body shapes.

cropped pants

There is a difference between pants that have been rolled short and pants that have been cut. The former speaks of easy cool, the latter of Italian dandy style – which some will find effortlessly chic, and others deplorably dull.

It’s certainly a trend of the last few years to show a lot of socks and it probably looks quite tired now, although showing an ankle – going sockless with loafers or sneakers – has a distinctly easy, high summer vibe. Note that this requires a tapered/narrow cut and should be trimmed conservatively. You don’t wear long shorts or three-quarter lengths (ever).

When it comes to dressing for work, take the Goldilocks approach: your pants shouldn’t be too long or too short, but just right, breaking gently over your shoe.

And one to swerve: The Skinny Cut

For many men, fashion’s fascination with skinny-cut trousers has been the bane of their wardrobe in recent years. Some have gone to the Stairmaster to have their calf muscles positively stretch their trouser seams to the breaking point. Others have no doubt filled a pair of socks where it counts to showcase their crown jewels even better.

Wisely, others have simply overlooked this trend and are now being rewarded with the fact that we come from the other side because 1) thin legs only look good on skinny men, and really terrible on any man who is vaguely fat or muscular , and 2) slim, rather than suffocating, is as far in as they will get to their trouser proportions.

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