1. Maynard G. Krebs

 

As the iconic beatnik of The Many Loves of Dobie Gillis, Maynard was the first official hipster of television. Part of looking cool is not caring if you look cool. That's the paradox of cool. And Krebs certainly could not care less. In 1960, his ratty, baggy sweatshirt and jeans were considered slovenly. Today, it's business casual.

Image: The Everett Collection

2. Mary Ann

 

Speaking of Bob Denver characters, let's hop over to Gilligan's Island. You might consider a Gilligan a perpetual style icon, what with his long-sleeve red polo, jeans and white kicks. But that bucket hat. Or perhaps you think Ginger, draped in glamorous gowns, is the obvious choice. She's a little too vintage red carpet. No, the true style icon on the isle is Mary Ann, the flyover-state farm girl with a penchant for short shorts. A close runner-up: The Professor.

Image: The Everett Collection

3. Mannix

 

For a guy who got whacked on the noggin each week, Mannix at least remembered how to look sharp. The detective toggled between two modes — business and casual. On the job, he tends to wear a ton of tweed. That vibe doesn't hold up quite as well as his off-hours ensembles. Take this denim-jacket-and-chinos get-up. That's a man comfortable in his masculinity.

Image: The Everett Collection

4. Agent 99

 

This Get Smart spy cherry-picked the best fashion of the 1960s, with an eye for what would last. While she never shied away from a good go-go mini, her trench foresaw the forthcoming androgynous trends. No wonder the Hollywood reboot essentially dressed Anne Hathaway in the same outfit, decades later.

Image: The Everett Collection

5. The Fonz

 

Jeans, white tee, motorcycle jacket. First perfected by James Dean. Never out of style. Case in point — the Fonz was the epitome of 1950s fashion in the midst of 1970s television. And he brought it all back. It trickled down through Grease and even the Ramones. It's stayed for good since.

Image: The Everett Collection

6. Freddie "Boom Boom" Washington

 

The Sweathogs of Welcome Back, Kotter all could pass for cool today. They are from Brooklyn, after all. Outcasts tend to look cooler in hindsight. That being said, Vinnie and Epstein got a little too giddy with the double-denim. Boom Boom was the coolest in the homeroom, his sleeves pushed up on his bright athletic jacket. 

Image: The Everett Collection

7. Diana Prince

 

Wonder Woman hardly shrunk into the background after she slipped into her alter ego. Diana Prince still popped out of any crowd, whether she was in the 1940s or 1970s. That's her secret. As a nearly immortal character, she has the benefit of living through wave after wave of style. At least, that's our theory as to how she dressed perpetually cool. Each episode offers up a handful of new looks. They all slay.

8. Rod Serling

 

Basic, you might argue. But consider the context. Serling was hosting his eerie anthology shows in the 1960s and 1970s. A man in a suit from that era can look quite dated. (See Mad Men for evidence.) On both The Twilight Zone and Night Gallery, however, Serling kept a crisp, tailored look. Like an Italian director. Sure, the tie got a little wider, but never to disco-clown proportions. He may not be a fictional character, but he earned his place on this list.

9. Josh Randall

 

Let's be frank. You could put Steve McQueen in onesie pajamas and he would still radiate cool. Even if he was wearing a beanie cap with a propellor — well, we'd want to look like him. But as bounty hunter Josh Randall on Wanted: Dead or Alive, McQueen made 19th century America the permanent template for men's style. Jeans, button-down, rugged jacked. That's all it takes. The holster belt helps, too. Just ask Han Solo.