Five Of Menswear’s Best Dressed Men

It’s no secret that many of the best dressed gents in the style spotlight aren’t entirely responsible for their impeccable appearance. At film premieres, album launches, award shows and other red carpet events, top stylists work feverishly behind the scenes to ensure their clients are well-turned-out. And it works.

But what about those men who are solely responsible for their on point style? Today, we sidestep the put-together celluloid, music and sports stars to showcase those whose aesthetic endeavours often go unnoticed.

Here are our top five best dressed men in the fashion industry – the inimitably stylish guys who don’t just wear menswear, they live and breathe it too.

Justin O’Shea, Buying Director At MyTheresa.com

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 MyTheresa.com (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.

Personal Lookbook

Justin O'Shea Personal Outfit Lookbook

Get The Look
  • Ps By Paul Smith Crosshatch Stretch-wool BlazerPs By Paul Smith Crosshatch Stretch-wool Blazer
  • Topman Black Suit WaistcoatTopman Black Suit Waistcoat
  • River Island Wool CoatRiver Island Wool Coat
  • Reiss Garth B Notch Lapel Blazer Bright BlueReiss Garth B Notch Lapel Blazer Bright Blue
  • Reiss Garth W Tailored Classic Waistcoat Bright BlueReiss Garth W Tailored Classic Waistcoat Bright Blue
  • Reiss Garth T Tailored Formal Trousers Bright BlueReiss Garth T Tailored Formal Trousers Bright Blue
  • Acne Studios Chelsea Cotton VestAcne Studios Chelsea Cotton Vest
  • Raleigh Denim Button-down Collar Printed Cotton ShirtRaleigh Denim Button-down Collar Printed Cotton Shirt
  • James Perse Crew Neck Cotton-jersey T-shirtJames Perse Crew Neck Cotton-jersey T-shirt
  • He By Mango Tailored Cotton-blend ChinosHe By Mango Tailored Cotton-blend Chinos
  • Charvet Paisley-patterned Silk TieCharvet Paisley-patterned Silk Tie
  • Ray-ban Polarised Rectangular Sunglasses With Tortoiseshell Arms And Brown Lenses Rb3502Ray-ban Polarised Rectangular Sunglasses With Tortoiseshell Arms And Brown Lenses Rb3502
  • Ted Baker Tutie Paisley Print TieTed Baker Tutie Paisley Print Tie
  • Asos Derby Shoes In LeatherAsos Derby Shoes In Leather
  • Dr Martens Made In England Core Les Lace Up BootsDr Martens Made In England Core Les Lace Up Boots
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.

Personal Lookbook

Jim Chapman Personal Style Lookbook

Get The Look
  • Asos Leather Biker JacketAsos Leather Biker Jacket
  • Asos Belted Trench CoatAsos Belted Trench Coat
  • Topman Brown Textured WaistcoatTopman Brown Textured Waistcoat
  • He By Mango Tailored Cotton-blend ChinosHe By Mango Tailored Cotton-blend Chinos
  • Reiss Huie Textured Leather Belt TabaccoReiss Huie Textured Leather Belt Tabacco
  • Topman Saxon Black Leather Monk ShoesTopman Saxon Black Leather Monk Shoes
  • Uniqlo Men Supima Cotton Crew Neck Short Sleeve T-shirtUniqlo Men Supima Cotton Crew Neck Short Sleeve T-shirt
  • Topman Slim Black TieTopman Slim Black Tie
  • Reiss Julius Wool Modern-fit Suit BlueReiss Julius Wool Modern-fit Suit Blue
  • Polo Ralph Lauren Cable Knit JumperPolo Ralph Lauren Cable Knit Jumper
  • Collezione Online Only Made In Italy Camel Hair Double Breasted Coat With WoolCollezione Online Only Made In Italy Camel Hair Double Breasted Coat With Wool
  • Reiss Toulon Suede Bomber Jacket GreyReiss Toulon Suede Bomber Jacket Grey
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.

Personal Lookbook

Milan Vukmirovic Personal Style Lookbook

Get The Look
  • Ps Paul Smith Shirt With Jungle Print Slim Fit Short SleevesPs Paul Smith Shirt With Jungle Print Slim Fit Short Sleeves
  • He By Mango Contrast Sleeve Bomber JacketHe By Mango Contrast Sleeve Bomber Jacket
  • Reiss 1971 Carlisle Contrast Raglan Jumper EcruReiss 1971 Carlisle Contrast Raglan Jumper Ecru
  • Allsaints Tonic Scoop TshirtAllsaints Tonic Scoop Tshirt
  • Allsaints Volt ChinoAllsaints Volt Chino
  • Allsaints Tallis TrouserAllsaints Tallis Trouser
  • He By Mango Slim-fit Dark Wash Tim JeansHe By Mango Slim-fit Dark Wash Tim Jeans
  • Ralph Lauren Classic Camo ShirtRalph Lauren Classic Camo Shirt
  • Esprit Aviator SunglassesEsprit Aviator Sunglasses
  • Jil Sander Striped Cotton SweaterJil Sander Striped Cotton Sweater
  • Etro Degrade-stripe Shawl-collared Cotton CardiganEtro Degrade-stripe Shawl-collared Cotton Cardigan
  • Drakes Blue Denim ShirtDrakes Blue Denim Shirt
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.

Personal Lookbook

Eugene Tong Personal Outfit Lookbook

Get The Look
  • He By Mango Wool-blend Straight-cut CoatHe By Mango Wool-blend Straight-cut Coat
  • Jack Wills Oxford Shirt With Short SleevesJack Wills Oxford Shirt With Short Sleeves
  • Eyevan 7285 Square-frame Acetate SunglassesEyevan 7285 Square-frame Acetate Sunglasses
  • Herschel Supply Co Glendale 5 Panel CapHerschel Supply Co Glendale 5 Panel Cap
  • Allsaints Warrut BeanieAllsaints Warrut Beanie
  • Nike Roshe RunNike Roshe Run
  • James Perse Crew Neck Cotton-jersey T-shirtJames Perse Crew Neck Cotton-jersey T-shirt
  • Nn.07 Charles Fine-knit Merino Wool SweaterNn.07 Charles Fine-knit Merino Wool Sweater
  • Reiss 1971 Zetland Relaxed Sweatshirt Grey Marl 69Reiss 1971 Zetland Relaxed Sweatshirt Grey Marl 69
  • Saint Laurent Leather-trimmed Wool-blend Varsity JacketSaint Laurent Leather-trimmed Wool-blend Varsity Jacket
  • A.p.c. Cotton-jersey SweatpantsA.p.c. Cotton-jersey Sweatpants
  • Common Projects Original Achilles Leather SneakersCommon Projects Original Achilles Leather Sneakers
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.

Personal Lookbook

Lawrence Schlossman Personal Style Lookbook

Get The Look
  • Topman Black Long Line Zip Through HoodieTopman Black Long Line Zip Through Hoodie
  • Asos Trench CoatAsos Trench Coat
  • American Apparel Fine Jersey Short Sleeve T-shirtAmerican Apparel Fine Jersey Short Sleeve T-shirt
  • Topman Jog On Grey Skinny JoggersTopman Jog On Grey Skinny Joggers
  • Topman Light Wash Classic Skinny Fit JeansTopman Light Wash Classic Skinny Fit Jeans
  • Ray-ban Clubmaster SunglassesRay-ban Clubmaster Sunglasses
  • Officine Generale Navy Unstructured Cotton-twill BlazerOfficine Generale Navy Unstructured Cotton-twill Blazer
  • Ami Chambray Cotton-denim Shirt 1005189Ami Chambray Cotton-denim Shirt 1005189
  • Reiss Cannes Bomber Jacket NavyReiss Cannes Bomber Jacket Navy
  • Asos High Top TrainersAsos High Top Trainers
  • Burton Beige Suede Desert BootsBurton Beige Suede Desert Boots
  • Adidas Originals Gazelle Og Suede And Leather SneakersAdidas Originals Gazelle Og Suede And Leather Sneakers
Final Word

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.

Who are your industry insider style icons? Anyone who should’ve made the list?

Comment below to let us know.