Get exclusive content, special offers and latest news delivered to your inbox.

Relaxed Trousers Are Officially In (& This Is How To Do It)

Is the skinny jean dead? Not quite…but there is new competition.

Is the skinny jean dead? Not quite, gents, but if the activity on the runway is any indication, it’s up for some decent competition.

Relaxed-fit pants have clawed their way out of the bin and have been embraced by a diverse audience, from Tyler the Creator to Nick Wooster and the impeccably tailored patrons of Pitti Uomo.

For those of you never quite sold on the shrunken, hyper-tailored looks of recent years, the relaxed cut has made something of a welcome comeback. Relaxed fit pants have plenty going for them – they don’t make an issue of the fact that you still don’t train legs, and add retro appeal to an otherwise ordinary outfit.

But it’s not just a matter of binning your tailored pants and then celebrating the fact that you no longer have to worry about a ripped crotch every time you sit down. There are a few ways to make the most of the trend and we’ve collected them for your next shopping expedition.

Relaxed, Not Loose

Curb your loose inhibitions

While there’s been a shift away from the thigh-gripping, confronting silhouette of the ubiquitous skinny jean, we don’t advocate firing your tailor. A slight taper – one that doesn’t expose the outline of your skinny, under-muscled calves the way your other slacks do – can make the difference by emphasising a casual, but still tailored, silhouette. 

Loose, billowing pants remind us of what you’ll find on clearance racks and rural op shops. In short, it just looks sloppy. Remember baggy jeans? Sure you do, and not without feeling like a twat. The work on the sewing board shouldn’t stop at tapering the trouser leg, either. Cropping the hems (even just slightly) is another simple way to own the style.

Cropped The Right Way

Relaxed, not slovenly

We’re not joking –  there’s no reason for your tailor to go out of business. Relaxed fit pants with a traditional break – folds of fabric that accumulate over shoes and bunch up like crumpled toilet paper – add bulk to the bottom of your legs.

No one is expecting a full tour of your sun-starved ankles, but a small concession to the cropped pant trend can tidy things up just enough. A half or no-break option – where the hem only just kisses the top of your shoes – looks much more deliberate, without risking the impression of being over-tailored. The key is to look relaxed, not slovenly. See our guide to cropped pants for a more detailed guide. 

Tailored Up Top

Don’t neglect the tailored shirts and jackets

Relaxed cuts or not, looking trim shouldn’t ever fall out of consideration. Contrast the relaxed pants with tailored shirts and jackets that show people you haven’t stacked on the kegs over winter.

If you don’t, you run the chance of looking bulkier (i.e, porkier) than you really are. Worse, it’ll seem like you run into difficulty finding your correct size (and no one heeds the advice of clueless blokes).

The obvious exception are those enviably cool streetstyle guys that do oversized clothes religiously, and somehow pull it off. But for regular guys (like you) who have the office or after-work boozing in mind and not the lenses of streetwear bloggers, tailoring should still be a part of the equation. 

Pleats Or Not?

Proceed with caution

Pleats: a source of sartorial controversy like no-sock suit ensembles, manbuns, and brown suits after the 70’s.

They’re the stylistic touch seen on the trousers of thuggish mafiosos in gangster films, and through the windows of prehistoric tailoring houses that exclusively service men over the age of forty. And believe it or not, they’re back in a big way.

Pleats are roomier and bring a bit of classic sartorialism into consideration. But like all temptations, they’re not for everyone. Pleats still call to mind the style preferences of stuffy old guys, and not everyone wants to look older than they are. If you’re a bit heavyset, or have hips that impress a midwife, pleats probably aren’t for you.

They add bulky folds of fabric across the midsection and can draw attention to your shape. Our tip? Proceed with caution.

Shoes For The Right Pants

Add high-top sneakers for streetstyle inspired looks

Because wider-cut, relaxed pants add bulk to your lower body, it stands to reason that your shoes need to balance everything out.

Sleek footwear – your favourite Neapolitan slip-ons for example – throw the proportionality of this look straight out the window. Your feet shouldn’t look shrunken, or hide underneath the hems of your pants (especially if you dropped some serious coin on them).

Instead, look toward chunky English-style brogues for smart-casual, or high-top sneakers for streetstyle inspired looks to add balance to the lower end of your outfit, and remind people that your feet didn’t stop growing in primary school.

Need More Help…

Here’s How Easy It Is To Dress Cool With Affordable Fashion Basics
These Are The 20 Best Jeans Brands For Men


Sign up now,
you magnificent bastard.

Access exclusive content, be the first to know about giveaways
and receive news before your mates.