Five Of Menswear’s Best Dressed Men

Photo of author

By WalterThornton

Justin O’Shea, Buying Director At

He may have spent his early years working down the mines of aboriginal Australia, but, today, Justin O’Shea splits his time between buying appointments and having his picture taken for pretty much every street style blog going.

Boasting a sizeable yet consistently kempt beard and a healthy dose of ink, O’Shea juxtaposes his rugged features with looks that are comparatively buttoned-up. It’s a clever blend of rock ‘n’ roll and refined tailoring influences that makes his looks so photogenic, whether it’s a printed short-sleeved shirt and tailored trouser combination or traditional three-piece suit.

In some respects a latecomer to the inner circle of the industry, O’Shea spent his twenties travelling and working at streetwear and denim retailers before joining the Neiman Marcus-owned (currently growing at a rate of 50 per cent year-on-year) in 2009. Along with overseeing continued success at the online retailer, O’Shea has garnered a following of over 58,000 Instagram followers for his mix of power tailoring and pops of attention-grabbing colour and pattern.

Slim trousers with boots are a mainstay in his wardrobe, as are the dark sunglasses – all in keeping with the rock influence that informs his style. Smartly blending classic and contemporary, O’Shea is one of the few who strike the balance well.

Jim Chapman, Vlogger

1.2 million Instagram followers, ladies and gentlemen. If you haven’t already – meet Jim Chapman, the YouTube vlogging sensation taking menswear by storm.

Part of a new wave of self-made celebrities, Chapman’s sprightly videos on subjects ranging from everyday life to the specific of men’s grooming and style have earned him an audience of over two million and counting.

Recently voted British GQ‘s Best Dressed Man Of 2015, the Norwich native’s take on menswear is timelessly stylish. He understands the basic principles of style and is a dab hand at proving you don’t need to wear a headline-grabbing statement piece to stand out. Clearly a classic tailoring devotee, Chapman’s most often seen in a tonal three-piece or mixing it up with suit separates: teaming smart trousers with a T-shirt or roll neck instead of a shirt.

Though neutral tailoring is this vlogger’s mainstay (particularly a bold camel double-breasted overcoat), his off-duty looks are equally well executed, often incorporating a slick leather biker jacket or luxe bomber and pair of straight-fit chinos or jeans.

Chapman won’t be credited for reinventing the wheel any time soon, but his mastery of iconic menswear pieces is second to none.

Milan Vukmirovic, Creative Director At Ports 1961

One of menswear’s longest-serving influencers, Frenchman and Ports 1961 men’s Creative Director Milan Vukmirovic has a résumé that reads like a who’s who of global luxury fashion.

Co-founder of cult Parisian concept store Colette, Vukmirovic worked alongside Tom Ford during his game-changing tenure at Gucci, and has held creative directorships at both Jil Sander and Trussardi. As if that wasn’t enough, he has also shot for the likes of Hugo Boss and Neil Barrett, and is the current editor-in-chief of Fashion For Men magazine.

No surprise then, that this busy man’s lauded personal style is all about effortlessness. In trim, model shape, Vukmirovic makes the most of his frame with pieces that are classically masculine in cut (short- and long-sleeved shirts, T-shirts, knitwear and a little tailoring) but decidedly contemporary in pattern or colour.

He also knows well the importance of clearly defining your personal style trademarks, with aviator sunglasses, a tightly shaved head and unbuttoned shirts all being Vukmirovic hallmarks.

Eugene Tong, Style Director At Details

Style director at one of America’s top men’s style magazines, Details, and a stylist for brands including Public School and John Elliot, Eugene Tong is one of the need to know names of NYC menswear.

A true high-low savant, Tong combines sharp tailoring with sports and streetwear pieces, lighting up the lens of many a street style photographer in the process. Unlike most of his list mates, he’s a kicks obsessive, often seen sporting the latest exclusive sneakers or opting for a classic pair of white trainers in place of brogues or Derbies to wear with a double-breasted overcoat or tailored joggers.

Dressing in a palette almost exclusively made up of neutral hues, Tong doesn’t stand out with colours, so much as cuts, textures and head-turning juxtapositions.

He’s the kind of guy who’ll think nothing of teaming Supreme with Margiela – probably starting a trend while he’s at it. Beanies are worn with shirts, and snapbacks are paired with conceptual tailoring pieces – and all the while Tong’s 56k+ Instagram followers are furiously double-tapping in appreciation.

Lawrence Schlossman, Editor-In-Chief At Four Pins

Arguably menswear’s most straight-talking commentator, Lawrence Schlossman is one half of the hilariously irreverent web show Fashion Bros! He’s also editor-in-chief at equally irreverent online men’s style magazine Four Pins and co-author of the menswear primer that pulls no punches: Fuck Yeah Menswear.

Much like his shifting role in the industry, Schlossman’s style has evolved from the #menswear uniform of natty tailoring, ties and monk-straps he sported while writing his own blog, Sartorially Inclined, to a deft mix of high-end and streetwear brands that reflects his full-time position at lifestyle magazine Complex.

Much like his unique tone of voice, Schlossman’s look usually says he knows menswear well but doesn’t take it all too seriously. Often relying on a palette comprised of neutrals and sticking to easy tailoring and smart-casual staples, he never oversteps the mark in order to court a photographer’s eye – even though most of their lenses are pointing in his direction anyway.

With the global menswear scene garnering more attention every season, it’s high time we celebrated some of its most original tastemakers. Superbly dressed and unquestionably influential, these five men make for a refreshing alternative to the usual – often professionally styled – best dressed list toppers.

‘Tis the season for hearty fires, hot, spicy ciders and – best of all – good-looking layers that thaw out any suggestion of a freeze on your winter style. Staying warm always looks cool when you invest in the right staples. And there’s nothing better to wrap up in than the new autumn/winter collection from one of the heroes of homegrown, British menswear.

Based in Long Eaton, near Nottingham, Sunspel has been handcrafting clothing for more than 150 years, using its own natural, sustainable, high-quality fabrics. The brand is particularly well known for its knitwear, T-shirts and underwear (James Bond’s favourite tees are Sunspel, in case you need any more persuading).

Sunspel’s autumn/winter collection is faithful to what its loyal wearers already love about the brand – understated, comfortable and ethically produced clothes that transcend not just the seasons, but traditional and contemporary, indoors and outdoors, smart and casual. And unlike your run-of-the-mill autumn/winter collections, it’s about more than seasonal greys and browns.