THE JOURNAL

Pitti Uomo street style in Florence, June 2015. Photograph by Ms Melanie Galea/thestreetmuse.it
While we wholeheartedly believe that a full-length hem – perhaps with a gentle break – will never be amiss in your wardrobe, there’s little denying that the ankle-baring movement has gained momentum of late.
Peek through the cobblestoned streets at Pitti Uomo: you’ll see worker trousers, lightweight chinos and stonewashed denim alike sporting a nonchalant roll.
Equal parts sartorial finesse and warm-weather relief, a simple trouser roll is a worthy way to add a punch of irreverence to casual ensembles. It works to emphasise shoes – perhaps a tan leather loafer or box-fresh plimsoll – and, ideally, a golden tan. But it’s also just an easy way to give your look a rakish, playful edge through the warmer months. So, how to do it right? Some rules are obvious: pair your roll with no-show socks; ensure you’re wearing shoes worth accentuating. But there are fine nuances worth observing, too. To get an expert view on the practice, we consulted Mr Jeff Lack, an Australian stylist whose Instagram feed amply demonstrates his own expertise in the art of trouser rolling. Scroll down for his off-the-cuff tips, which no man should be without this summer.

Rolling up denim
A single, prominent roll plays especially well with heavier selvedge denim. “I like the rockabilly 3in single roll myself,” says Mr Lack. What’s crucial, though, is keeping the outfit in proportion: a thicker roll will better complement chunky lace-up boots than flat sneakers, for instance. Either way, know your context. “Rolling cuffs on denim to wear with sneakers works better than rolling with smart shoes,” says Mr Lack.
Rolling up chinos
Chinos (and lightweight denim) are prime targets for a relaxed roll or two. The key? Don’t let it look too clinical. “A 1in roll two to three times does the trick,” says Mr Lack. After rolling, give the cuff a few tugs to loosen things up. Naturally, this look works best with slim, tapered trousers, though there are ways around that. “If the hem is wider in finish you can pinch and roll to achieve a more tapered look,” says Mr Lack.
Rolling up suit trousers
“Just don’t,” begs Mr Lack. Instead, opt for a tailor-installed cuff. “On plain fabrics, a four- or five-centimetre cuff is cool.” The new cuff should fall just above your laces for a modern, streamlined finish. For more distinctive suits – especially those with patterned trousers, Mr Lack suggests a crop: “Patterned trousers can be cuffed or cropped – whatever floats your boat.”
Don’t overlook the crop
“Rolling is being taken over by cropped tailoring,” says Mr Lack. “This tailoring usually hits or rests just above the ankle bone protruding from the outside of your foot.” But while a cropped trouser is becoming more and more prominent, Lack warns against building too vast a collection. “If we take heed of runway shows, it’s clear that we are heading away from this trend and back towards slouchy, drapey finishes,” he says. “Proceed with caution.”