What could the past possibly teach us about modern dressing? In a word: everything. When it comes to fashion, it’s all history repeating, which is why classic pieces remain triumphant time and again. Certain clothes are eternal and will never do your closet wrong, like these five essential pieces etched into our collective consciousness since an era before Instagram. They’re as iconic as the men who made them must-haves.

The crewneck. It doesn’t get more timeless than this go-to sweater.

Must-Have: Crewneck Sweater

As worn by: Steve McQueen, king of cool

Devilishly disheveled and charming as hell, McQueen had an untouchable confidence that made the most basic sweaters, khaki trousers and even polo shirts street-tough and motorcycle-ready. The lesson learned? The classics look just as good beat-up as they do brand new. Just add swagger.

The way we wore: neutral chinos, stripes and slip-ons, Paul Newman-style.

Must-Have: Chinos

As worn by: Paul Newman, the guy next door

Newman proved the perfect pair of chinos was, and still is, everything. A shining beacon of American-classic minimalism, he was also known for slim-fitting suits, crisp oxford shirts and the trench. When all else fails, take your cues from him and reach for a white undershirt and chinos. And that grey hair? Nothing is more debonair.

Have yourself a Cary Grant moment in a dapper BR Monogram suit.

Must-Have: The Suit

As worn by: Cary Grant, the suave-est gent

Arguably the most influential style icon who ever lived, Grant is synonymous with the perfect suit. He reportedly never dressed for the moment, instead mixing casual and formal elements for timeless, slick appeal. Let him serve as a reminder you should own at least one spectacular, well-fitting suit to make you the quintesential ladies’ man.

Nothing says Dean like slim, rugged denim and a well-fitted tee.

Must-Have: Dark Denim

As worn by: James Dean, sex symbol

A heartthrob of few words—and endless outwear options that immortalized him. To capture an ounce of Dean’s cool, rebel with purpose in slim, straight-leg denim, paired with touches of leather or a sports jacket with a slim tie. Pompadour optional.

Must-Have: Linen Button-Down

As worn by: Harry Belafonte, king of calypso

Belafonte’s seductive breed of island-cool was larger than life, and is brought to life by our limited-edition, artisan-crafted Piece & Co. collection. Think fluid prints that channel a smoldering essence. Wear a printed button-down alone or under a blazer for a summer look that’s on-point