Men: don’t be afraid of style! Being stylish is not the same as swallowing every trend the fashion industry tries to spoon-feed you. No sir. “Fashions fade, style is eternal,” as the great Yves Saint-Laurent once said. Men like Paul Newman and Miles Davis knew this innately, and luckily, the elements that solidified them as “style icons” are right at your fingertips. Let’s take a look back at these classically cool dressers and how you can get their steeze, piece by piece.

Miles Davis


It was often said that Miles Davis wore the looks of the future, and by 1960 he was already lauded as one of the best dressed men out there. Always ahead of the fashion pack, his style evolved with the times rather than becoming stuck in one moment. Though Davis wasn’t afraid to get a little wild as the decades wore on, he knew what staples were timeless—tailored chinos and a pair of go-to loafers.

Hornberg Shawl Collar Sweater, Rag and Bone; Hand painted Ombre Scarf, John Varvatos; The Protégé twill pants in Cornsilk, AG; Kane loafers, Hudson.

Cary Grant

The elegant Cary Grant always looked like the perfectly understated gentleman. Three-piece suits, a Windsor knot and solid colors made up Grant’s core style, which can be summed up simply and with one word: Timeless. Browse through old photos of Grant and every outfit you’ll see him in translates seamlessly to today.

Patron Coat V1, Surface To Air; Chamber waistcoat, Phillips Blazer, Blade IV trousers, all by Rag and Bone; Oxford shirt, Band Of Outsiders; Delsin brogue, Ted Baker.

Paul Newman

paul newman_sidebyside

Though he nailed the perfectly tailored suit when appropriate, Paul Newman’s everyday clothing choices leaned toward what any guy can get behind—worn in jeans, comfy tees, oxford button downs and his signature v-neck sweater. Newman managed to look unfussy yet impeccably put together. And always classically masculine.

West Point Chino, Wings+Horns; Milton textured shawl cardigan, Reiss; Crew-Neck T-Shirt, Vince;  Style Minimal watch, Officina del Tempo; Jack Purcell Peter in navy, Converse.

Woody Allen



When it comes to classic style, Woody Allen might not be the first to jump to mind. But take a second look and you’ll see the poster boy for every nerd/hipster/quirky filmmaker this side of the Brooklyn Bridge. With his uniform of plaid or solid button downs (often worn under a pullover sweater), khakis and his signature black-rimmed glasses, Allen has disregarded trends so completely that he has become the trend.

Panto glasses, K&B; Indigo Oxford Plaid, Gant Rugger; Zaine Clifton pant in light brae, Theory; Catch Wax moccasin, Base London.