Receive a free copy of our magazine when you sign up.

Here’s The Right Way To Wear Cropped Pants & Jackets

The complete guide to cool cropping for a men’s wardrobe.

In the farshun realm of menswear, the cropped-or-not debate stirs up enough vitriol that you’d (almost) be pardoned for forgetting about the recent tensions on the Korean peninsula or the fact that rock legends Hanson will be touring Australia. We hear this argument all the time. Can/should I wear shorter pants? Does a biker jacket make my torso look stunted? Why do I even care about these things?

Let’s face it – some guys want to shorten, crop, and hem their clothes. Many do not. Either way, this trend hasn’t been cropped out (sorry) of the picture in 2017. While we hope that you have more important things on the horizon than the length of your pants or jacket, this guide will put you on the right track.

It’s got a brief overview on style and execution, and some pointers based on your lifestyle and body type. Then you can go back to guiltily listening to MMMBop while your better half is out.

The Crop-or-Not Debate


So where did it all begin? Wearing cropped clothes isn’t exclusive to the 21st century. A cursory glance at images from any Pitti Uomo will demonstrate how Italian men have been embracing cropped trousers for quite some time. Shorter jackets – bombers, varsity, and biker styles – have been longstanding wardrobe additions for decades, so it’s hard to argue that this is purely a recent trend.

But it’s New York designer Thom Browne who is commonly attributed (or blamed) with the emergence of ‘cropped’ suits for a wider audience. His suit blocks are known for taking everything up a few inches, to such an extent that many consider it his sartorial fingerprint.

It didn’t take long for this to enter the mainstream. Since the mid-to-late 2000’s designers on and off high street – from Tom Ford to Topman – have experimented with shorter cuts, boldly tailored hemlines, and an embrace of the exposed ankle. This has enraged tailoring purists.  It’s facilitated a long-standing argument whether men should consider clothes short enough to deck out their brother in high school. That is entirely up to you. We think it’s entirely possible to wear cropped pants and jackets without being laughed out of the country – just keep the following pointers in mind.



Short pants have been routine invitees on the runway. Although the pendulum has begun to swing the other way, cuffed pants don’t seem doomed to sartorial infamy any time soon. To put you in good stead, we have a few pointers on the how-to and how-not-to.

Cropped pants are best reserved for warmer months, and casual environments. That’s not to say your no-break suit trousers must stay in the closet all winter, but it’s a reasonable mindset for general wear. You generally have more flexibility if the dress code is relaxed and you aren’t expected to impress any corporate minders with your pasty ankles.  Think a weekend in the Cayman Islands (if you’ve been saving diligently) or just a midday jaunt to the pub in summer (if you haven’t).

However, cropped trousers are on the ‘progressive’ end of tailoring. This means their utility in the office is limited, unless your bosses are sartorially accommodating or it’s a casual environment where a suit and tie aren’t preconditions for being taken seriously. Keep it to after-hours dress in general.

RELATED: 5 Ways To Rock White Pants & Look Cool Doing It

Cropped pants showcase your footwear. A full hem, especially one with a traditional ‘break’ over the shoe, draws attention away from and essentially obscures your shoes. With a crop, they’re on full display. So, make sure you’ve mastered the essential end-of-week polish, that you’ve swapped out those musty white shoelaces, and the leather hasn’t cracked (if you need help, check out our guide on shoecare).

Trendy as they are, cropped pants come with strings attached. Cropping trouser legs can visually shorten the bottom half of the wearer. If you topped out under six foot, don’t be too trigger happy at the tailor. You want your legs to seem longer, so you therefore look taller. Conversely, tall gents shouldn’t expose too much man-ankle –  this can in some cases affect the proportions if you have a long upper body.

There’s plenty of ways to skin a cat. These four methods are popular ways to crop or shorten trousers and you should find one that’ll do the trick.

Plain Hem


The plain hem is the cleanest, and simplest option for a cropped trouser leg. There’s not much to it. The hem ends in a horizontal line, without any cuffs or folds of fabric. The advantage of this style is its cleanness and simplicity. It doesn’t add any weight to the bottom of your leg in the way a cuff would. This is beneficial to shorter men who want to draw attention away from their predicament, and it’s usually most office-friendly. Ask for a ‘no-break’ hemline at the tailor. This simply means that the trousers don’t bunch or crease over your shoe. He’ll know what you mean. Remember, shorter = less conservative.

Rolled Cuff


This option is self-explanatory: you hold the trouser hem in an even line, so the fabric doesn’t bunch up, and then roll it. The fabric thickness will determine how many times you need to roll it. Heavy selvedge denim might just need one roll, but a thin linen-cotton chino might ask for a couple more. This is easier than the pin roll, and a good option if you don’t require a slimmer line on the trouser. 

Pin Roll


Fear not – you won’t risk impaling your ankles with a pin on this one. All you need to do is tightly pinch the loose trouser hem, and fold it horizontally towards the back end of your ankle. After you’ve got it in place, roll it once, twice, and again for good measure. This method traps the loose fabric inside a firm cuff. The result is a narrower hem opening that offers a flattering and slim taper. There are video tutorials online, but if a dopey style copywriter can get it right, you shouldn’t have too much trouble.

Turn Up/Cuff


This is a comparable method to the rolled cuff, but applied to tailoring. The ‘turn up’ (Brit slang) or cuff (American slang) is a style of hem where extra fabric at the bottom of the trouser is turned outwards, then stitched and pressed to hold its shape. This creates a visual block above your ankle and frames your footwear. It’s not as common as a plain hem, but you wouldn’t know it based on the menswear blogosphere. There’s no need to whip out the scissors and try this at home. Find a solid tailor and he’ll do the rest. You just need to specify the size of the cuff (4-6cm looks the best in my unsolicited opinion). Cuffs accumulate more dirt and dust, so be mindful of that if your suit aftercare is a bit lacklustre.

To Sock Or Not?


If you do the rounds on #sprezzatura, it’s likely you’ve seen photos of cool old Italian guys smoking, bantering, and wearing cream linen pants and loafers with no socks. What these dashing images fail to capture is the fact that eschewing socks is a tragedy of hygiene (although we’re sure those guys know what’s up too). That’s because feet really, really sweat. They accumulate foul odours well before you’ve plonked yourself down on a barstool and ordered the first of eight Negroni’s. So always wear socks, gents. Even if it’s just the invisible kind that hide beneath your ankle. This will allow you to enter polite society without making every girl at the bar wonder if your approach to podiatric hygiene is demonstrative of other problems in your life.



Cropped jackets have generally belonged to the fairer sex, but there’s a few notable exceptions with which you can fill out your wardrobe – most notably the biker and bomber jacket. We’d recommend experimenting with different lengths in the rest of your outfit, and mucking around with layers to

It may sound counterintuitive, but cropped jackets can benefit our shorter brothers. This is because the jacket won’t conceal the bottom half of your body, adding some length to your overall figure. On the other end of the spectrum, tall gents should proceed with caution. This is simply because a taller person will have a longer torso, and a cropped jacket can magnify any imbalance that develops from wearing a short jacket. Not a fixed rule by any means, so test different options in the mirror and see how your proportions shape up as a result.

The Biker Jacket


Buying a black leather motorcycle jacket is an aspiration in the hearts of most men. They’ll probably never go out of fashion, and can turn any suburban schmuck into a something more of a sartorial threat.

You’re probably familiar with the jacket’s origins. Marlon Brando, James Dean, and a succession of imitators made this jacket a quintessential piece of ‘I’m a badass (or trying to be)’ sartorialism. It’s now a runway staple and worn by countless dudes worldwide (few of whom will be a rebel on a wicked motorcycle).

The Bomber Jacket


If the name any clue, you’ll know that the bomber or flight jacket (like many awesome menswear pieces) originated amongst fighting men. Their backgrounds are steeped in the world wars, where flying officers were required to equip themselves with thickly insulated jackets to keep them warm at extreme altitudes.

Subsequently, they crept up in popularity towards the tail end of the 20th century. There’s a ton of options on the market – shearling, oversized, and embroidered variants, among others – and the past 12 months have seen them in just about every store you could imagine.

How To Pull It Off


Although no one can argue with the timeless simplicity of a plain white tee with either of the above, there’s a couple ways you can tweak the jackets and experiment with the cropped silhouette.

Some guys have been splicing the shortened hemline with longer kit elsewhere. A common favourite is to mix up a short jacket with an oversize, longline tee. This can soften the severely cropped silhouette of a biker jacket, and fill out the gaps between the hem of the jacket and your pants. Add a pair of Common Projects white sneakers and tailored cargo pants (Zanerobe blockshot chinos are a safe bet) into the mix and you’re set.

Additionally, complementing a shorter jacket with extra layers has lots of potential. A popular sartorial pastime, layering (with anything from a denim overshirt to a thin grey hoodie) can work wonders to a cropped jacket. This gives you the opportunity to incorporate contrasting colours into your outfit, and use different textures and fabrics to spruce up an outfit that’s becoming monotonous. Make sure the jacket isn’t too snug so your layers have room to work their magic.

Cropped Menswear Do’s & Don’ts

Bottom Half

Do taper the trouser leg if you crop the hem. Loose, short pants will create a look of dishevelment in a tailored or ‘cocktail’ outfit. Streetwear, not so much, but it’s a good general rule for smarter clothes.

Don’t go too short. No one wants to see you in your father’s capris. Be conservative with alterations; 1 to 2.5 inches shortening is plenty.

Do pay attention to the seasons. Cropped chinos in summer with loafers are the business. Cropped suit pants in winter means wet socks before you get to the office.

Don’t risk an aggressively cropped trouser in a traditional office environment, especially without socks. The ‘short-pants guy’ down the hall probably doesn’t get end of year bonus.

Do use a rolled or cuffed hem to emphasize footwear. Baggy cuffs obscure the good stuff.

Don’t form your entire trouser collection around cropped pants. It’s handy to have traditionally-cut trousers lying around in case you get conscripted into a work conference, reluctant in-laws’ dinner, or other miscellaneous event where your spunky socks or ankles aren’t welcome intruders.

Top Half

Do wear a cropped jacket if you find that you’re the type of dude who goes on his tippie-toes in group photos. Shorter jackets show more trouser, lengthening your lower body to some degree. It won’t make you six foot whatever, but hey, it’s something.

Don’t wear a cropped jacket if you’re ‘big boned’. A longer jacket can draw attention away from a prominent midsection. If you’ve been smashing knockoffs and late night Chinese take-away, a cropped jacket will aim a laser at your indiscretions.

Do keep in mind that a shorter jacket reduces the length of your torso. If you’re tall, a heavily cropped jacket can risk you looking like your clothes were shrunk at the dry cleaners, or that you’re too useless to find the correct size.

Don’t take the advice of upjumped copywriters as sartorial gospel – experiment with cuts that appeal to you and if it works, feel free to tell us to bugger off (not that we’ll listen).


Sign up now,
you magnificent bastard.

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