Is there anything more satisfying than bossing an outfit your mates can only dream of pulling off? Than triumphantly succeeding where other men fail?

Probably, but not having hordes of other guys aping your look is a pretty sweet sartorial spot to be in. And that’s exactly what’s on the table if you’re up for wearing your clothes oversized. Longline-loving, proportion-playing, silhouette-shifting pieces offer a way – despite their already popular status – to cut through menswear’s masses and make your style known.

Why? Because almost everyone already towing the long line is failing hard. This is a trend – and we won’t pull the wool over your eyes (and down to your knees) here, it’s a trend – that many attempt, but few make work.

Here’s the long and short of copping some of Yeezy’s devil-may-care sartorial swag.

1. One Piece At A Time

If this is your first time stepping up to the long line, tread carefully. When dealing with silhouettes this far-reaching, it’s alarming how swiftly a shirt turns into a dress, so dip your toe before trying to layer longline pieces.

A dropped hem T-shirt, jacket or coat is a good place to start. Choose a length that’s slightly longer than what you’re accustomed to, wear it a few times, and then – in what’s not unlike a round of style-related gradual exposure therapy – add inches to your limit with longer pieces.

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2. Oversized Isn’t Office-Ready

A longline piece’s charm lies in its ability to inject some effortless swag into your look, so it follows that it’s probably not going to win you any brownie points with your boss.

That’s not to say that it won’t work for slightly more dressed-up off-duty occasions, though – like that Tinder date; try a shirt layered underneath a longline jacket for a look that says you know fashion without taking yourself too seriously.

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3. Keep The Balance

Key to styling longline pieces is sticking them on the front line, allowing their exaggerated silhouette to take centre stage while the rest of your look keeps shtum. Make the mistake of oversizing everything and you’ll, at best, look like a model that forgot to change after a Comme des Garçons casting; at worst, like Fagin.

“Keep your jeans/trousers as slim as possible when wearing longer-length outerwear or tees,” says model and influencer Chris John Millington. “Anything wider in the leg can create an unflattering look.” Put simply, an oversized T-shirt or shirt makes a great companion for skinny jeans, but pair one of these with some billowing wide-legged trousers and bam, it’s Hammertime.

Balance is even more important if you’re vertically challenged, so avoid shortening your legs by swamping them with a hemline that plunges south. Instead, try wearing a longline cardigan with a regular T-shirt to tap the trend without losing valuable inches.

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4. Monochrome’s The Word

Playing fast and loose with your hemlines is a pretty radical statement in menswear terms. Add busy prints and patterns into the mix and you’ve got yourself a look that’s good for little else other than getting digs and giving headaches. Ditto showy colours.

Instead, stick to block-colour pieces in shades that don’t scream for attention (navy, black, white) – tasteful, but with a twist.

john elliott ss16john elliott ss16

5. It’s All In The Fabric

As a rule of thumb, cotton and synthetics lend themselves well to longline pieces due to their drape and stretch, while denim and linen can also be cut to make garments with more dramatic drops.

Corduroy, textured weaves and ribbed fabrics, however, cannot. So avoid those, and any other fussy materials, like a devastating plague.

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Key Pieces: T-Shirts & Vest

New to longline? Then try a simple T-shirt or vest for an entry-level way into the trend.

Proving that the oversized tee isn’t just for sullen teenagers slamming doors and sulking in the bedrooms, Fendi’s SS16 take on the off-duty staple is a masterclass in steering oversized from slovenly to stylish.

If you’ve not got the budget to blow on one of Fendi’s top-end tees, you’re going to need to be clever in how you dress yours up. Try teaming a T-shirt or vest with black or charcoal wool trousers (slim please, see earlier point re: Hammertime) and finish the look with some heavy-soled Derbies or Oxfords and a longline bomber jacket or your go-to mac/parka. Easy as.

Alternatively, take your cue from stylist and creative Nas Abraham by playing silhouettes off each other: “A longer shirt falling out of the back of a cropped jacket adds a sense of separation to your outfit and always looks good.”

Men's Fashion & Style - Longline T-Shirts Outfit Inspiration Lookbook

zarah&m ss14i love ugly ss16pull & bear 2015

Key Styles

  • Selected Homme Longline T-shirtSelected Homme Longline T-shirt
  • Asos Longline T-shirt With Crew NeckAsos Longline T-shirt With Crew Neck
  • Topman Grey Marl Long Line T-shirtTopman Grey Marl Long Line T-shirt
  • H&m Long T-shirtH&m Long T-shirt
  • River Island Grey Longer Length Loose Fit T-shirtRiver Island Grey Longer Length Loose Fit T-shirt
  • Zara Long T-shirtZara Long T-shirt
  • Rick Owens Long-length Jersey T-shirtRick Owens Long-length Jersey T-shirt
  • 3.1 Phillip Lim Longline Cotton Sateen T-shirt3.1 Phillip Lim Longline Cotton Sateen T-shirt
  • Topman White Slub Long Line T-shirtTopman White Slub Long Line T-shirt

Key Pieces: Shirts

Longline tees and vests skew too casual for you? Then try a smarter take.

Oversized shirts offer a buttoned-up spin on this silhouette-extending trend, and provided the fit’s more natty than nightgown, it’s hands-down the sleekest way to look sharp. If you really want to prove your style stock, opt for a granddad collar design – a natural fit for a longer length (think Nehru vibes) – but a regular semi-cutaway collar works, too.

As with tees and vests, the same rules apply to your bottom half: steer slim to skinny, whether you’re combining your longline shirt with ripped jeans or smart trousers.

Men's Fashion & Style - Longline Shirts Outfit Inspiration Lookbook

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Key Styles

  • Adpt Longline Grandad Denim Shirt In Regular FitAdpt Longline Grandad Denim Shirt In Regular Fit
  • Solid Longline Shirt With Grandad Collar In Regular FitSolid Longline Shirt With Grandad Collar In Regular Fit
  • Asos Check Shirt In Super Longline With Grandad Collar In Long SleevesAsos Check Shirt In Super Longline With Grandad Collar In Long Sleeves
  • Ami Alexandre Mattiussi Long ShirtAmi Alexandre Mattiussi Long Shirt
  • Engineered Garments Long Tonal Check ShirtEngineered Garments Long Tonal Check Shirt
  • 3.1 Phillip Lim Oversized Shirt3.1 Phillip Lim Oversized Shirt
  • Comme Des Garcons Homme Plus Classic Black Longline ShirtComme Des Garcons Homme Plus Classic Black Longline Shirt
  • Rick Owens Rick Owens Cyclops Faded Stone Wash Oversized ShirtRick Owens Rick Owens Cyclops Faded Stone Wash Oversized Shirt
  • Topman Premium White Longline Long Sleeve Smart ShirtTopman Premium White Longline Long Sleeve Smart Shirt

Key Pieces: Outerwear

As much as we love and cherish the inherent masculinity, unequivocal cool and ease of wear of a bomber jacket, we’ve seen it so many times over the past few seasons that something had to give.

Enter the longline bomber – an extended version of the menswear classic that often comes without its usual elasticated hem. Favoured by the likes of London father-son design duo Casely-Hayford, it’s all the things you love about a bomber, but with even more of the wind-deflecting coverage.

Elsewhere, at the likes of E. Tautz and Agi & Sam, the overcoat has gone supersized, nodding to the relaxed tailoring of Armani-ruled 1980s-era America – think Richard Gere in American Gigolo brought bang-up-to-date for AW16.

“If you’re going for the oversized look, some coats can – depending on your frame – be a bit more difficult to pull off, but the key is to contrast it against something more fitted,” says Abraham. “Too much oversized can make you look, well, oversized!”

Men's Fashion & Style - Longline Outerwear/Jackets/Bombers Outfit Inspiration Lookbook

bershkah&mh&m autumn 2015topman spring 2016

Key Styles

  • Asos Longline Bomber Jacket In WhiteAsos Longline Bomber Jacket In White
  • Asos Super Longline Bomber With Raw Edge And ZipAsos Super Longline Bomber With Raw Edge And Zip
  • Longline Collarless JacketLongline Collarless Jacket
  • Topman Black Longline Mac JacketTopman Black Longline Mac Jacket
  • Topman Black Long Line Scuba ParkaTopman Black Long Line Scuba Parka
  • River Island Khaki Longline Waterfall Hooded JacketRiver Island Khaki Longline Waterfall Hooded Jacket
  • H&m Long Bomber JacketH&m Long Bomber Jacket
  • Raf Simons Isolated Heroes Oversized Cotton-twill Hooded ParkaRaf Simons Isolated Heroes Oversized Cotton-twill Hooded Parka
  • Selected Homme Mens Berlin Bomber JacketSelected Homme Mens Berlin Bomber Jacket

Final Word

Are you convinced by the sartorial plus points of oversized clothing or do you steer more conservative with your silhouettes?

Drop us a (long)line below.