Prior to becoming one of photographer Scott Schuman’s subjects on OG street style blog The Sartorialist, fashion entrepreneur Alessandro Squarzi was little-known outside of his native Italy. Thankfully, that chance passing between the two has spawned a steady and impressive documentation of Squarzi’s wardrobe ever since.
Flitting between elegant comfort and Pitti peacockery without so much as breaking a sweat, this man about Milan doesn’t shy away from trending pieces but always wears them in an effortless way. And if you ever needed a visual representation of why every man needs a strong outerwear game, Squarzi provides it.
No street style list worth its salt would be complete without arguably the world’s most-watched male supermodel. David Gandy may have gotten his start on breakfast TV, but he’s since gone on to front campaigns for the likes of Dolce & Gabbana, Banana Republic and Marks & Spencer.
Fittingly for one of London Fashion Week Men’s most prominent ambassadors, Gandy’s wardrobe regularly leans heavily on British tailoring. But it’s not the just timeless stuff – the checked three-pieces and elegant jacket-T-shirt-trouser get-ups – that Billericay’s finest has down pat. He’s also a master of casual tonal looks, too. Another reason to secretly hate him.
Even if you’re not familiar with Eric Rutherford by name, you’ll almost certainly have come across shots of his perfectly coiffed silver hair and ultra-sharp wardrobe, which effectively amount to a definitive handbook on how clothes should fit.
One of those maddeningly versatile types who can pull off just about anything, no two of the American model’s outfits are ever the same, whether it involves cutting a rug in a roll neck or making chinos look peak Riviera. Rutherford is walking proof that men in their middle age can run rings round the young guns in the style stakes.
Still don’t get the concept of sprezzatura? Ask Frank Gallucci. The native Calabrian has been instrumental in putting Pitti Uomo on the street style map, with his signature mash-up of Italian tailoring and smart-casual shirt-trouser combos fasting becoming one of the main attractions of the bi-annual menswear event.
As a former model, Gallucci’s lucky draw in the genes department certainly help make his moves in the wardrobe department stick, but it’s the way he makes statement pieces look so easy that earns him a place in our hall of fame.
Johannes Huebl is one half of the world’s most genetically blessed couples, so he could pretty much wear the most uninspiring outfit imaginable and still scrub up well. Huebl’s not one for resting on his genetic laurels, though, and makes sure he’s always out repping Club Menswear better than pretty much anyone we can think of.
What you won’t get here is daring or cutting-edge. What you will get is blueprint after blueprint for outfits that will look just as good IRL as they do sauntering past a battalion of street style photographers. Plus the occasional shot featuring Olivia Palermo. So it’s a win-win.
It’s not every men’s style hero that got his start in mining. But Justin O’Shea, the former creative director of Italian menswear label Brioni and founder of self-funded menswear label SSS World Corp 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.)
The Germany-based Aussie’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 – sets street alight with punky spark.
The only thing more impressive than Milan Vukmirovic’s CV – he co-founded Parisian concept store Colette, worked alongside Tom Ford as design director at Gucci and is the editor-in-chief of international style magazine L’Officiel Hommes – is his own personal brand of menswear magic.
The key? An unwillingness to be pigeonholed. Vukmirovic’s mastery of diverse genres is unrivalled. Statement outerwear? He’s done that. Neutral toned tailoring with razor-sharp cuts? Easy. Rugged and updated workwear classics? A dab hand, too.
AKA ‘The Woost’, ‘The Woostgod’, one of the best-dressed men of all time. At 56 years of age, the fashion exec-turned-menswear designer pushes the boundaries of style further than guys half his age – a fact his 730k Instagram followers and work with Thom Browne, Ralph Lauren and Calvin Klein are a testament to.
You could say it was Wooster that made #menswear as we know it. Before him – his shorts suits, liberal patterns and 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. Then buy up every collaboration he comes out with.
Sure, models get paid to look good, but far from being just another mannequin with a pulse, Oliver Cheshire is just as much menswear substance as he is style.
When he’s not inside on the runway, Cheshire manages to steal the limelight outside the shows with his impeccably put-together looks, which run the gamut from dressed-down tailoring to streetwear made smart. If ever there’s an up-and-coming trend that we’re ambivalent about, all it usually takes is Cheshire wearing it to tip us over to fanboy territory.