Winters Past

20th Century Fashion from Deco to Disco

Men In Hats

Men, I understand the baseball cap. I really do. It’s easy, it’s practical, it’s the male equivalent of flip flops and yoga pants.

But sometimes you long for a little something extra: a little panache, a little style, right?

So try a classic men’s hat silhouette. ¬†And go for vintage. It’s going to be of better quality than it’s modern counterpart and it’s going to have that slightly worn in quality that ups the cool factor.

First, the cowboy hat. The curved brim gives it a little slouch and swagger.

men in cowboy hats

Ralph Lauren, Sidney Poitier, Steve McQueen, Paul Newman

Next, the newsboy or flat cap. It’s as easy as a baseball cap, but classier.

men in flat caps

Leonardo diCaprio, David Beckham, Idris Elba

Of course, there’s the fedora. Again, a vintage one is going to have that patina that makes it easier to wear.

men in fedoras

Ol blue eyes, Denzel Washington, Robert Redford, Sean Connery

While I’ve championed the beret as an easy starter hat for women, it’s ¬†perhaps a little more of a challenge for men. A few have made it their signature look, so let’s focus on them. Look at Dizzy Gilispie (always a style icon), Thelonious Monk and, in modern times, Samuel L. Jackson. All three choose hats with a bit more structure and they wear it tilted back just a little bit.

men in berets

Dizzy Gilespie, John Lennon, Jack Nicholson, Thelonius Monk

men in berets

Samuel L. Jackson, Cary Grant, Juan Paul Belmondo,

I leave you with Brad Pitt, a true chapeau chameleon.

brad pitt in hats

brad pitt in hats

Author: Winters Past

I am a vintage clothing shop owner living and working in rural north Florida. I believe in adding a little vinegar and molasses to my greens, having my coffee outside whenever possible, and mixing something vintage into every room and every outfit.

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