The Posthumous Pantheon: 10 Menswear Icons Who Will Never Go Out of Style

From Peter O'Toole to Prince, a look at the timeless cool of some of history's most memorable dressers

August 18, 2021 9:48 am
The Posthumous Pantheon: 10 Menswear Icons Who Will Never Go Out of Style

Earlier this year, I compiled a list of the 50 best dressed men over 50. These were men who have cultivated a signature look for decades, not men whose claim to style fame owes to some stylist who is adept at dressing them for red carpets. These are men who look great whether they’re at a blockbuster premiere or out running errands; men who know the importance of good tailoring and of dressing to accentuate their own attitudes and personas.

But there were some men who felt like glaring absences from that list, who defined what it meant to be well dressed their entire lives but are no longer with us. Men like Paul Newman and Gregory Peck. Some are close to my heart — like Jimmy Stewart and Peter O’Toole, who were among my first crushes (when I told my therapist this she laughed for three whole minutes). There are others whom we lost too soon, like Prince and Anthony Bourdain. Some of them are obvious style icons (Peck), while others were more quietly stylish their whole lives, like Ed Bradley. All of them are owed a debt of gratitude by every single stylish man today. 

So without further ado, here are the 10 best dressed men whom I imagine are still pulling together top-shelf fits in the sartorial utopia in the sky.

Community Clothes/Mr Porter

Gregory Hines 

Gregory Hines is a legend. What fellow best-dressed man Mikail Baryshinokov is to ballet, Hines was — and remains — to tap: an all-time great, the mold in which other dancers can only aspire to fit. And his sense of style befits his legacy. For decades he graced stages and red carpets in relaxed button-downs and pleated trousers, classic fit suits and blazers and shirts opened midway down his chest. Everything Hines wore fit him with a breeziness that moved the way he did: with superlative ease. 

Steal the look: Community Clothes mens chino, Gabriela Hearst linen shirt

The Rake/Mr Porter

Peter O’Toole 

Full disclosure: Peter O’Toole is my favorite man on this list. He’s my number-one crush of all time, he’s the first celebrity death that made me cry. O’Toole was an impish delight and his style reflected that; he moved seamlessly from traditional English tailoring to more flamboyant apparel; he wore bow ties and heavy black framed cat-eye glasses. He wasn’t afraid to take risks either — in one of my favorite photos of him, he’s wearing suede ankle-length jeans with panels down the front. In another he’s wearing a hybrid desert boot monk strap that is perhaps the finest looking shoe I’ve ever seen. He wore neck scarves and herringbone jackets and he pulled it all off with a boyish charm that he radiated right up until he passed. 

Steal the look: Lardini double breasted sweater, Polo Ralph Lauren blazer 



The best way to describe Prince’s style is it’s an orgasm for your eyes (and if you look long enough, for other parts of your body, too). Leather, lace, heels, assless pants: Prince wore it all in a way that made you question why any other kind of menswear even existed. For an entire decade (if not longer), he had us questioning why every man wasn’t wearing heeled boots and high-waisted lamé pants. 

Steal the look: Be Prince 

Cifonelli/Mr Porter

Ed Bradley 

Every week my family sits down to watch 60 Minutes together. And even at a young age, Ed Bradley stood out to me. Before I could really understand what he was reporting on or the impact of the work he did, I knew he looked so fucking sharp. His signature earring, his newsy suits offset by a bold shirt or tie … to me he was everything a journalist was supposed to look like: serious but not stuffy, classy but human. 

Steal the look: Cifonelli collarless shirt, Gucci herringbone coat 

The Rake

Paul Newman 

I’m pretty sure Paul Newman invented cool, whether playing opposite Elizabeth Taylor in Cat on a Hot Tin Roof, racing cars or cozy at home with his beloved wife Joanne Woodward, Newman was a style icon. And of course it doesn’t hurt that he’s quite possibly the hottest man to ever live. Newman’s style — like his acting chops — was versatile: sweaters layered over oxfords like a prep-school boy ready to break your heart; field jackets and deconstructed blazers; sportcoats and easy white shirts; not to mention perfectly on-trend suits, from preppy tweeds to wide peak lapels. 

Steal the look: McLauren sweater, Anderson and Shepperd corduroy field jacket 

Mr Porter

Gregory Peck 

If you hear the name Gregory Peck and don’t immediately think of an absolutely sublime outfit, there is something wrong with you. After he wore something, it might as well have been retired for good, because no one will ever be able to match him. Peck could wear it all: double-breasted suits, easy linen shirts, three-piece suits with waist coats, sweater vests, aviator sunglasses. He could be the stern academic or the rogue sex symbol. And there will never be another like him.

Steal the look: Dalcuore Grey plaid sportcoat, Turnbull & Asser button down collar shirt

Mr Porter

Anthony Bourdain 

When we lost Anthony Bourdain, we lost a giant in the food and travel world, but we also lost a style icon. Bourdain’s rugged, easy style was as much his signature as the tenor of his writing prose — a desert boot, slim jean and linen shirt that looked as though it had been rolled into a ball for two months in a suitcase — yet he still always looked like the coolest fucking guy in the room, not to mention the proud owner of a sunglasses collection that would put the greatest aficionados to shame. And Bourdain knew how to clean up nice, too; for red carpet appearances, he wore dark monochromatic suits tailored to perfection, but often paired suit jackets with jeans or formal outfits with sneakers, never letting us forget his down-to-earth core. 

Steal the look: Rubinacci linen shirt, Edward Green chukka boot

Mr Porter/The Rake

Jimmy Stewart 

Jimmy Stewart was one of my first crushes; I saw Rear Window in high school and was immediately smitten — and who wouldn’t be when someone can look that hot in nothing but pajamas for an entire two-hour film? But Stewart’s sartorial repertoire far extended the crisp cotton PJs he wore while spying on the neighbors with Grace Kelly. Offscreen Stewart is perhaps one of the best dressed men in history; when I was sourcing images for this article, almost every guy had one or two misses because, well, who hasn’t? But not Stewart. Every outfit from his youth right up until his old age was impossible to improve on. Lush double-breasted suits, knits that would make you think sweaters were invented for the sole purpose of dressing him. Timeless, classic — Stewart is a menswear blueprint for the ages. 

Steal the look: Thom Sweeney double breasted blazer, Cad & the Dandy tweet jacket  

Mr Porter

Frank Sinatra 

What would a list of the best dressed men be without old blue eyes? The Italian crooner’s relaxed gangster style defined a genre and melted hearts around the world. Frank Sinatra’s suits were what you’d expect of the time: mid-rise trousers and double-breasted jackets with wide lapels. But Sinatra had a knack for looking perfectly styled but slightly, intentionally tousled (or what the Italians call sprezzatura) — a tie loose around his neck or a hat worn slightly askew lent him an aesthetic that radiated sensuality. 

Steal the look: Husband’s paris pinstripe suit

Mr Porter

Christopher Lee 

Christopher Lee was your classic English gentleman with an added dose of drama. Perhaps it’s my knowledge of the types of roles he played (brooding and macabre), perhaps it’s his foreboding stature (he was 6’4). But I’d argue his sartorial twist on the Savile Row aesthetic also played a large part. Sure, there were plenty of red carpets and appearances where Lee looked the part of an Englishman, with tweeds, classic-cut suits and the like. But he liked to have some fun, too: bold knits, creative layering with waistcoats and polos, suede field jackets, a playful pocket square here and there. Like his most famous roles, Lee avoided subtlety, but it was never at the expense of taste. 

Steal the look: Dries Van Noten blazer, Tom Ford suede jacket 

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