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How To Rock Cropped Trousers (Like An Italian)

What started out as a vero Italian style trait, has now become a global fashion trend. And one that’s proving to have vero stay-power. We’re talking about the cropped trouser. From suit separates to jeans, the short-leg pant has trickled down from Florentine flamboyancies witnessed at Pitti Uomo and moved onto the more fashion-forward abroad.  And nowadays, mainstream menswear is making the most of the cropped trouser, too.

RELATED: How To Dress Like An Italian

While the bared ankle (or mankle) takes time getting used to, we’re seeing more of the cropped trouser in the office (with socks, of course) and almost everywhere on the weekend: from the rooftop bar in summer to nighttime weddings in autumn.

Feel like you’re the only one not rocking the cropped trouser? Or maybe you’ve tried the mankle look, and failed, due to too much exposure. Fear not, we’ve got the intel on how to wear cropped pants laid bare below. And what shoes work best, to boot.

Then, click through the slideshow for ways to rock the cropped trouser (like an Italian).

How To Wear Cropped Pants With Perfection

How To Wear Cropped Pants

As the cropped trouser continues its furore, many menswear brands are releasing pre-cropped varieties, as part of their regular collections, alleviating the need for men to roll or fold pant hems to get the short look.

But, we’re fans of doing things on our own (I mean, who doesn’t like a bit of DIY action?) First up, we’ve laid out three main ways to crop your trousers, using the regular length trousers you already have at home. Not handy? Just go out and buy a pair cropped trousers, instead. Here are three ways on how to wear cropped pants.

Loose Fold

How To Wear Cropped Pants

Taking a pair of your favourite trousers, simply fold or roll (loosely) the hem, two to three times, finding a trouser height that looks stylish, but never contrived. The no-fuss manoeuvre adds a tapered edginess to normal-length trousers and works particularly well with lightweight chinos or selvedge denim.

The Tight Roll 

How To Wear Cropped Pants

The tight roll is thinner and more cinched than the loose fold. Start by thinly folding the fabric of the hem, followed by rolling it (like you would a piece of flatten bread dough) over and up, onto itself. Stop at your desired height – never more that a few inches high.

The tight roll is more casual the the loose fold: ideal for styling jeans (to show off your luxury leather sneakers) and create a cool streetwear base to any outfit.

The Once-Up


Clean and sharp, the once-up fold is designed to crop dress trousers or separates with a subtle precision. The look turns weekday suit pants into weekend wonders, and makes mundane winter suits feel summery again, with a bit of exposed ankle.

Ironing the turn-up fold (and then pinning it for extra security) will keep the crop in place. But, if you’re intent on keeping the pant cropped, visit a tailor and have them alter the hem permanently.

Sock It

The cropped trouser will – more often than not – require ankle exposure. For those up to speed with common-sense hygiene, wearing shoes – sans socks – in summer, can only end one way: sweaty and smelly feet; the odour setting up home in your spotless luxury kicks or leather brogues.

Invisible socks or sockettes are indeed, the answer. Despite their daintiness, these obscure foot covers are indeed, man-material, and come made without the sock trunk, so your mankles remain blissfully exposed, without fear of smelling.

It’s A Shoe In

Now that we’ve separated the folders from the rollers (and the lovers of the pre-crop) on how to wear cropped pants, knowing what shoes and pants to wear together – with your exposed ankles between the two, is the final component.

Sneaker Freaker


The low-cut, white sneaker is a perfect pairing with a light cropped trouser or a wool-cotton trouser separate in the cooler months.  Worn with a revere collar shirt and vintage shades, summer becomes cool once more, as a Talented Mr. Ripley-style dream team.

For the sock wearer, black cropped trousers pair well with dark coloured socks, opting for a pattern or bolder colour sock to disrupt the minimalism. White socks and sneakers are a nod to the ‘normcore’ trend (think Seinfeld), but it’s not so ‘Jerry’ when paired with a boat neck waffle neat in off-white; more Scandinavian and chic. Add a satiny bomber for a play on texture and an extra edge to your contemporary sports look.



Purely for summer, espadrilles were made for the cropped trouser. For a smart casual ensemble, look to white or khaki chinos and long-sleeve jersey shirt, with the sleeves nonchalantly pushed back. It’s a great driving outfit too, alongside your favourite leather duffle bag and shades; the crop giving you extra room to move.

RELATED: 5 Simple & Stylish Ways To Wear White

For an easy day at home – on the lounge or out back on the deck, slide into a pair of relaxed-fit cotton pants, the hems rolled tight, creating a cinched shape that mirrors the drawstring pull of the waist. The crop helps reign in the oversize nature of the loungewear, without compromising comfort and leg room.

Boots ‘N’ All


The opposite of the espadrille, the dress boot is perfect for winter or wet weather blues. And it sits nicely under a rolled denim jean or casual trouser. And the versatile boot comes in a variety of workable silhouettes. The dessert in dark tan or brown suede works well with raw denim jeans, the underside of the selvedge denim forming a white cuff on the ankle for a heritage twist.

RELATED: A Simple Guide To Men’s Dress Boots

The tight roll or fold up works well, ensuring the hem kisses the top of the tongue – never covering the boot (the whole idea of the roll is to shorten the leg) for the full cropped effect.  And, unlike the aforementioned, boots require socks – sans exception. Play with a speckled marl in winter to lift the textured of something black and slick when going minimal.

Dress It Up


The cropped smart trouser is the piece de resistance this season in menswear. It’s clean form and natural fabrication make it the perfect transitional trouser – be it, for day-to-night dressing or from unpredictable weather, changing from summer to winter and back again.

And the lace-up dress shoe, brogue or derby, is perfect for cutting a refined figure under a slim-fit cropped trouser. The sophisticated peg or one fold is the key crop hem here – nothing messily rolled, ensuring the shoe isn’t too chunky or overbearing with metallic appendages (the trousers are already ‘fashion’ enough so keep the leather lace-up classic).

Wide-leg denim – coolly distressed and faded – also works with this shoe, especially with a vintage, burgundy shoe or tan brogue with a rounder toe. Again, go for no socks, but add a pair (maybe match them to your pocket square when wearing a jacket) in winter or when dress codes requires it – weddings and night-time engagements.

Click through the slideshow for ways on how to wear cropped pants (like an Italian).



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