8 Men’s Street Style Legends

8 Men’s Street Style Legends

What started as a few candid snaps has been blown up into a million-dollar business. Street style, the modern-day phenomenon that sees us dissect what fashion shows’ attendees are wearing as much as what the models on the runway are, has come a long way from a small group of bloggers surreptitiously snapping on the sidelines.

And for the most part that’s good. What’s not to like about seeing menswear’s insiders flexing their style might, setting trends and at the same time giving us a blueprint for how to broach them ourselves?

Well, nothing really, apart from the fact that a lot of what’s shot isn’t worth the bits on a memory card. Which is why it’s time to honour the men sidestepping outlandish (and frankly bad) style for the sake of it. The anti-peacocks. The men confident enough in their own importance to not bother about getting dressed with the sole purpose of getting snapped. Which, of course, makes their outfits all the more lens-worthy.

Bruce Pask

For a man that grew up in the desert, Bruce Pask knows layering. Currently Men’s Fashion Director at legendary New York store Bergdorf Goodman, Pask has honed his eye with stints at major titles like GQ and the New York Times’ T magazine. But it’s his uncanny ability to wear two jackets at once that’s seen him skyrocket through the street style ranks.

Pask is best known for almost single-handedly popularising the outerwear layering trend. Whether it’s a denim jacket and a wool overcoat, a gilet and a topcoat, or a blazer and a parka, this street style stalwart nails his silhouette every single time.

Bruce Pask Fashion and Style Outfits

Frank Gallucci

Still don’t get the concept of sprezzatura? Ask Frank Gallucci.

Proof that Italians do it better, native Calabrian Gallucci has been instrumental in putting Pitti Uomo on the street style map: his signature mash-up of Italian tailoring and smart-casual shirt-trouser combos has fast become one of the main attractions at the biannual Florentine showcase.

As a former model, Gallucci’s lucky draw in the genes department definitely helps make his style moves stick, but it’s the way he makes statement pieces look so easy that makes him worthy of our hall of fame. No one looks this good in a cobalt blue suit.

 Fashion and Style Outfits

David Gandy

No street style list worth its salt would be complete without arguably the world’s most-watched male super.

Billericay-born Gandy might have gotten his start on breakfast TV show This Morning, but he’s since gone on to front campaigns for the likes of Dolce Gabbana, Banana Republic and Marks Spencer; against the odds, some might say, in an industry dominated by super-lean male models whose bodies are more beanpole than brawn.

A long-time client of listmate Joe Ottaway (below), Gandy’s personal style is similarly tailoring heavy. Fittingly for London Collections Men’s (soon to be London Fashion Week Men’s) most prominent ambassador, his wardrobe borrows heavily from British tailoring’s big hitters including Thom Sweeney.

But it’s not the just timeless stuff – the checked three-pieces and the elegant jacket-tee-trousers getups – that the Gandyman’s got down pat, he can push the boat out too. Take, for example, the look bottom-right. On anyone else it’d frankly look crazy, but on Gandy, fitted snug and accessorised with shades and a furrowed brow, it just works.

 Fashion and Style Outfits

Joe Ottaway

Flanking David Gandy is no mean feat, but London Collections Men fixture Joe Ottaway takes it all in his immaculately suited stride.

Personal stylist Ottaway is best known as the brains behind David Gandy’s killer wardrobe, but his own sartorial line-up is equally impressive. A sharp mix of Savile Row suiting and old-school Hollywood, his style epitomises the modern gentleman, without skewing dandy. Not bad for an Essex boy.

 Fashion and Style Outfits

George Cortina

It takes serious style not to be overshadowed by a woman like Anna Dello Russo. But George Cortina – veteran fashion stylist and Dello Russo’s Vogue Nippon associate – more than holds his own with the larger-than-life Italian icon on his arm.

The key? Statement tailoring. Cortina’s mastery of the double-breasted blazer is unrivalled; fitted just slim enough and most often styled with a pair of cropped tapered trousers and some classic black monk-straps, it’s a masterclass in modern-day power dressing. Not to mention how to nail mankles.

 Fashion and Style Outfits

Karl-Edwin Guerre

Most photographers – street style or no – rely on a fashion week wardrobe of jeans and a jacket with more pockets than a roadman’s (all the better for storing kit). Not so Karl-Edwin Guerre, the lensman whose eclectic style has seen him appear as much in front of the camera as behind it.

Part-Pitti flair, part-Brooklyn swag, Guerre’s eye-catching blend of lightweight tailoring, bright colours and statement hats has meant his looks are as well documented on other influential street style blogs as on his own, the much-followed Guerreisms, founded in 2008.

If you’ve been looking for a way to wear a punchy palette and pattern (without veering into the peacock paddock), then you’d do well to get to grips with Guerre’s feed.

 Fashion and Style Outfits

Justin O’Shea

It’s not every men’s style god that got his start in mining. But Justin O’Shea, Italian label Brioni’s newly inaugurated creative director, isn’t your average man in fashion: he’s got tattoos, works out and rocks a ducktail beard that once sent the internet into hysterics when he decided to shave it off. (Don’t worry, it’s back.)

O’Shea’s strength lies in his ability to splice rock-inspired and refined styles: shades and fully-inked sleeves worn with a three-piece suit; or a white vest and smart black high-waisted trousers. The kind of looks that – when surrounded by overly preened, predictable ensembles – set menswear fashion weeks alight with their punky spark.

Then again, what else would you expect from the man that cast Metallica in a major fashion ad campaign?

 Fashion and Style Outfits

Nick Wooster

AKA ‘The Woost’ AKA ‘The Woostgod’ AKA one of the best-dressed men of all time. At 56 years of age, self-proclaimed “free agent” Nick Wooster pushes the boundaries of style further than guys half his age – a fact his 642k Instagram followers are testament to.

You could say it was Wooster that made #menswear as we know it. Before him – his shorts suits, his liberal camo, his patchwork tailoring and his iconic handlebar moustache – we had little in the way of inspirational show regulars. Or, at least, none who courted Scott Schuman’s and Tommy Ton’s cameras so well.

Watch. Learn. And then buy up every collaboration he comes out with.

 Fashion and Style Outfits

Want more of our street style coverage? Click through to the daily updated FashionBeans street style gallery.

For tips on how to tap the trends on the streets, check out our guide to the key street style trends from the latest men’s fashion weeks.

With over eight years’ experience writing on men’s style, former blogger Cillian O’Connor delves deep into men’s collections, sorting the wheat from the chaff to deliver seasonal trends and failsafe style tips.

He has written for Metro, The Business of Fashion, The Irish Times, and Canvas8, and has consulted for brands including Gillette and Dan Ward.

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