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A Gentleman’s Guide

The Keys To Streetwear

Initiate yourself into the prevailing mood in menswear by following these simple steps

  • Leandro Justen/

Are you truly urban or merely urbane? Either way, streetwear should now be on your radar. And to those who have been thriving on a steady diet of tailoring for the past decade, incorporating it into one’s repetoire can be intimidating – a bit like being the protagonist in one of those comedies where you wake up in a slouchy adolescent’s body. Worn well, streetwear says, “I’m part of something, and I believe in it”. Worn badly, it says in a voice reminiscent of Mr Jason Bateman, “Oh, man, am I old!”

The term itself is tricky to define as it is used to describe a constellation of trends – luxury athletic wear being one and an abiding interest in looks pioneered by skateboarders, punk rockers and 1980s rappers being another. There’s also an element of thrift-shop archivist to streetwear as the core components are items that you probably already own: a varsity jacket, a sweatshirt and gleaming white sneakers.

In any case, however you define it, streetwear is increasingly, ubiquitous, thanks to its ongoing infiltration into the world of high-end style. This movement has been spearheaded by the likes of Balenciaga, Givenchy and Lanvin, who regularly incorporate elements of the street in their seasonal collections, but it’s also represented by a slew of newer brands such as VetementsOff-White and Fear of God, which is another way of saying, “This is what the cool kids are wearing”.

Given the above, we at MR PORTER thought it was high time we issued some sort of guidance as to how to incorporate streetwear into your wardrobe. Here are our rules of the road.

Wear it Oversized

  • Marc Richardson

Let’s start this segment with an apology to all the readers out there who have spent hours in the gym sculpting an impeccably V-shaped torso to look imposingly wonderful in a slim-fit henley T-shirt. Because streetwear is baggy and shapeless and… well, this is awkward… you’ve pretty much wasted your time. For the rest of you: enjoy the unrestricted feeling of wearing a shirt, sweater or jacket that is in fact, or has been designed to look like it is, at least one size too big. As for how to insert such pieces into your outfit, we suggest combining multiple items in layers over a pair of knee-length shorts. A final point: shirts should have at least one if not all of the buttons undone to keep everything nice and loose.

  • Off-White Logo-Print Cotton-Blend Canvas Jacket

  • Vetements Printed Mélange Cotton-Jersey T-Shirt

Wear Your Logo with Pride

  • Adam Katz Sinding

In the luxury world, at least since the late 1990s, it’s become a bit of a no-no to walk around with a logo on your chest – such ostentatious show-offery, so goes the consensus, is in poor taste. In streetwear though, a logo signifies a little more than just how much you paid for something, it’s a badge of honour and an acknowledgement that you’re aligned with a particular style tribe. Given this, sporting your favourite brand’s logo is completely permissible, whether it’s on a logo tee, cap, sweatshirt or bomber jacket. Just make sure not to overdo it, by which we mean stick to one (max two) logos at a time. It looks a bit promiscuous and – dare we say the unspeakable word – inauthentic if you’ve got hundreds vying for attention simultaneously. One extra tip: logos that hail from places far from your current GPS location get big style points. A Malibu surf shop’s T-shirt is as good in Paris as the above Chinese Nike logo flip turns heads in London.

  • Gucci Logo-Print Loopback Cotton-Jersey Hoodie

  • Balenciaga Oversized Printed Cotton-Jersey T-Shirt

Make A Statement

  • Adam Katz Sinding

Streetwear is a subcultural affair, created for and by a series of skaters, punks and anti-establishment kind of guys. This means it has never been shy of grabbing attention with the odd slogan, and neither should you. How, though, to get away with sporting a hyperbolic statement without looking like a bratty kid on the one hand, or a horribly un-chaotic and un-legendary old-timer on the other? The picture above has a fantastic solution to this conundrum in its pairing of grey tailoring (usually spotted in offices and at weddings) with sneakers, a cap and a pair of tees covered with assorted stick-it-to-the-man messages. On the one hand it’s square, on the other it’s irreverent (particularly the tying of the jacket round the waist – not that we would necessarily recommend doing this with your latest Berluti purchase). The contrast works, and taps into the knowing irony that is the bedrock of a good streetwear look.

  • Maison Margiela Printed Cotton-Jersey T-Shirt

  • Balenciaga Slim-Fit Printed Cotton-Jersey T-Shirt


  • Christopher Fenimore

Incorporating an element of streetwear into your outfit can be a more subtle business, particularly given the preponderance of high-end track pants currently on offer from brands across the board. In the image above, a pair with an elasticated waistband and rolled-up cuffs has very successfully taken the place of a pair of chinos. The baggy fit of the T-shirt and bright white sneakers, of course, also add a bit of casual swagger to the look. These could also be paired with an oversized, baggy shirt if you so wish, but we would recommend you stay away from wearing track pants with highly tailored items such as the structured or double-breasted blazer.

  • Norse Projects Luther Nylon Cargo Trousers

  • Common Projects BBall Leather Sneakers

Wear a cap with your blazer

  • Søren Jepsen

Baseball caps are a streetwear essential, and, though formerly banned from most runways, have, in the past decade, been slowly making an appearance on those most hallowed stretches of polished flooring, too (Mr Lucas Ossendrijver at Lanvin was a frontrunner here – he’s been fielding high-end caps as far back as 2007). It seems the right time to announce, therefore, that a cap can be worn with a tailored jacket, not in a tweed-y, fusty, aristocratic way, but as a clash of idiom reminiscent of Mr Spike Lee (who is able to wear a cap with anything and pull it off). Just make sure that it’s part of an outfit that, overall, is casual, comprising jeans and chinos and of course, sneakers – the world is not quite ready for a cap and a three-piece suit.

  • Givenchy Logo-Jacquard Canvas Baseball Cap

  • AMI Grey Slim-Fit Mélange Virgin Wool Suit Jacket


  • Guerreisms

Military surplus has also had a strong influence on streetwear. Adding a streetwear edge to your outfit can therefore be as simple as choosing a piece in camouflage, currently available in the collections of many beloved brands including Valentino, Givenchy and Saint Laurent, as well as street-inspired marques such as Chimala and Neighborhood. Though it might seem a busy print, camouflage is, of course, designed to blend in with its surroundings and so is mightily flexible. Opt for a single piece (an accessory is the easiest) as a splash of colour against navy tailoring or a black bomber jacket.

  • Valentino Camouflage-Print Canvas Pouch

  • Polo Ralph Lauren Logo-Appliquéd Camouflage-Print Fleece-Back Cotton-Blend Jersey Sweatshirt


Though shoes tend to make and break an outfit, in streetwear, they are the alpha and omega, the lynchpin of it all, which means they not only need to be chosen for maximum impact, but should be looked after with terrifying passion. It’s a good general recommendation therefore, to pick a pair of sneakers that will contrast the colours of your outfit, and so stand out. Plain denim, for example, works well with patterns and prints. Beige chinos (of the Dickies variety) will complement a bright colour such as red or green. Predominantly though – such is the current style climate – you will be wearing black clothing and white sneakers, as in the above image. There’s something particularly appealing about this combination, harking back as it does to the days of hip-hop pioneers Run-DMC. It only works, though, if you spot clean your adidas after each and every wear with warm water and a damp cloth, so they retain their pristine whiteness. If you’re anxious about doing this right, head straight to this week’s video on looking after your sneakers.

  • Pilgrim Surf + Supply Cropped Wide-Leg Cotton-Corduroy Trousers

  • AMI Leather-Trimmed Suede Sneakers