'90s TV Characters with the Coolest Sports Swag

It was the best of times, it was a vest-y time.

The '90s were a blinding storm of rayon rains and magenta monsoons, and just about every day featured a 100 percent chance of denim.

There wasn’t much to do besides be awkward around members of the opposite sex and engage in the occasional zoom-a-zooming, so we stayed inside with Friends and enjoyed the golden age of cable television.

“Swagger” as we know it now didn’t exist back then, considering our favorite television characters were too busy pioneering it to give it a name. 

The following are 15 TV characters from the '90s that pushed the limits of sports fashion. They wore “swag” before it was it was a thing, and their choice of gear set the tone for every modern sneaker head and hoopster to ever don a Starter jacket.

15. Kevin and Brittany (‘Daria’)

Kevin, the jock, and Brittany, the cheerleader, from the animated series Daria, literally lived in their sports gear. 

Brittany wasn't good at many things (besides complaining), but she did a bang-up job of promoting the vintage USC-style cheerleading outfit.

Kevin also deserve credit. It takes a man to rock shoulder pads and a '70s neck roll to class every day—a man who wants to sleep sitting up without his head falling over.

14. Jesse Katsopolis ('Full House')

Have mercy.

This image of Uncle Jesse rocking out in a baseball jersey is as American as a Big Mac wrapped in the Declaration of Independence, with a side order of grammatical errors.

That’s patriotism—beautiful, sporty patriotism.

13. Cousin Skeeter (‘Cousin Skeeter’)

The Michigan Wolverines have taken a page out of Cousin Skeeter’s book and went with the clean maize-on-maize look for their uniforms, with a sprinkling of blue.

As usual, the brilliance of '90s fashion was about 15 years ahead of its time.

12. Chalky Studebaker (‘Doug’)

Such a bro.

Chalky Studebaker was the most athletic and most swaggin-est of Doug Funnie’s friends.

Every day of his life this kid rocked a purple and pink letterman jacket, and he made it look good. That’s something Macklemore couldn’t even do. 

11. Robbie Sinclair (‘Dinosaurs’)

From what I can recall, Robbie Sinclair wasn’t the best character on Dinosaurs (that distinction belonged to Baby Sinclair) but he definitely was someone who’d describe himself as “radical.”

Between the letterman jacket and prehistoric PF Flyers (not Converse, not in my mind) he possessed the closest approximation to swagger as existed on Pangea, and is the earliest known relative of the modern lax bro.

10. Jerry Seinfeld (‘Seinfeld’)

“Swag” is not a term typically associated with Jerry Seinfeld’s taste in clothing, but an unknown fact is that the man had a bigger sneaker game than most sneakerheads out there today.

Complex.com’s Gary Warnett chronicled this weird fact with “A Complete Guide to Seinfeld’s Sneakers,” a slideshow detailing the 50 some-odd different pairs of athletic sneakers Jerry rocked over the course of Seinfield’s nine seasons. 

What you see here is Seinfeld kicking around in a pair of Nike Lava Flow Royal Blues—the only hiking shoes for a comedian who lives in a New York apartment.

9. Al Bundy

Even now, Al Bundy’s No. 33 jersey hangs proudly in the imaginary rafters at Polk High.

The man was never quite able to shut up about his high school jock days, but you can’t blame him. Al Bundy scored four touchdowns in one game, and it was the greatest achievement in anyone’s lifetime.

If he wants to keep wearing his jersey beneath his letterman jack, well, we can only respect the look.

8. Zack Morris ('Saved by the Bell')

He liked to keep it preppy, but the few times Zack Morris endeavored into the world of athletics, he’s returned home a champion soaked in the tears of his vanquished competition.

Actually, Zack’s only real athletic achievement was winning third place at an All-City cross country meet that one time, but the track suit he wore, that’s worth more than any medal.

Honorable Mention: Screech wearing a wig with a basketball uniform.

7. Gerald Johanssen ('Hey Arnold!')

Arnold’s best friend wouldn’t be caught dead without his No. 33 outfit on, and he had some sleek matching red sneakers to boot.

Gerald Johanssen was also the king of the hair on Hey Arnold!, featuring a towering flat-top that even Nerlens Noel would envy. 

6. Global Guts Contestants (‘Nickelodeon Guts’)

More like AGGRO SWAG.

I'll see myself out.

5. Malibu (‘American Gladiators’)

What is there to say about Malibu’s gear that hasn’t been said about countless other fashion masterpieces? While striking as a whole, the glory is in the details.

Like other gladiators, Malibu had a sweat-wicking American flag halter top and spandex boy shorts, but did he stop there? Nay, he plowed onward, adding Oakleys and growing his plumage into that of a blonde Troy Polamalu. For posterity.

That’s how you commit to your craft. 

4. Mr. Cooper ('Hangin' with Mr. Cooper')

Hangin’ With Mr. Cooper wouldn’t have been the same show if wasn’t for the man’s style.

Mr. Cooper (played by Mark Curry) wore leopard vests and royal blue suits, but the piece de resistance was his signature tie covered in more sports equipment than most men could handle.

Where other men’s spines would bend under the weight of so much awesomeness hanging around their necks, the NBA-player-turner-substitute-teacher stood tall.

His neighbor Tyler also rocked a Brett Favre jersey, which was a hipster choice for a kid living in Oakland, Calif.

3. A.C. Slater (‘Saved by the Bell’)

If you don’t know about tucking your high school football jersey into your jeans, then you know nothing, Jon Snow.

A.C. Slater is high fashion married with sports. You can’t teach a guy to be comfortable with tucking his numbers into a pair of Wranglers, and trying to force him into a male ballerina suit will only end up in handfuls of awkwardness.

Those are skills your are born with, and Slater is the only man on record who can pull off both and still stand a chance with Kelly Kapowski. 

2. Denver ('Denver the Last Dinosaur')

Haters will hate, and prehistoric skaters will skate.

Denver the Dinosaur only aired until the end of 1990, but that doesn’t matter considering he was a dinosaur that rides a pink skateboard with matching sunglasses and an electric guitar.

The show was about conservation and ecology, but clearly toxic levels of swagger were running off the page when illustrators crafted this gemstone. 

1. Will Smith ('Fresh Prince of Bel Air')

This is it. We’ve found it. This is the greatest picture ever.

It just doesn’t get any better than Michael Jordan hanging out with Kid ‘N Play, Will Smith and DJ Jazzy Jeff.

But focus—or try to—on the crispiness of Will Smith's attire. That’s a Chicago Bulls Starter jacket and a matching Bulls snapback. Sure, this isn’t Will from Fresh Prince of Bel Air, meeting Michael Jordan, but they were basically the same person.

Also worthy of note is Will's ability to turn any outfit—no matter how goofy—into one of the best get-ups you've ever seen.