Men
Cracker Jack Boy
Originally called “Candied Popcorn and Peanuts”, Cracker Jack was sold at the first Chicago’s World Fair. Not only is it well known for coming with a prize, but it will be forever linked with baseball as sung in “Take Me Out to the Ball Game”.
Vanilla Ice
Try as he might to make a new name for himself, Robert Van Winkle, better known as Vanilla Ice, will always be remembered for such classics as “Ice Ice Baby” and “Ninja Rap.” While the rapper now dresses like a member of Limp Biscuit, it’s his hi-top haircut and harem pants of the ’80s that make his costume fun to imitate.
Flavor Flav
Hip-hop pioneer, Flavor Flav has stayed true to his style despite adding reality television star and restaurateur to his resume. Combining lots of “bling” with a giant clock necklace, copying Flavor’s style probably won’t score you a model like Brigitte Nielsen but it will have people asking you for the time.
Bad Grandpa Irving Zisman
Jackass presents 86-year old Irving Zisman (Johnny Knoxville). He’s on a cross-country trip with his young grandson Billy, and they’re raising hell all the way. Irving is gonna show all the young’uns what it means to be Bad Grandpa.
Al Bundy
In Married… with Children, Al (Ed O’Neill) is head of the Bundy household. As a high school football player he once scored 4 touchdowns in one game, but he now struggles through his job selling women’s shoes and his hopeless family. Al’s only reprieve is his alone time on the toilet and on the couch watching episodes of Psycho Dad.
Cliff Huxtable
One name is synonymous with ugly sweater: Cosby. On the Cosby Show, Cliff Huxtable (Bill Cosby) immortalized the ugly sweater, taking it beyond anything we’ve seen before or since. The nice thing about these crazy patterns is that no one would ever notice if you got Jell-O pudding on them.
Jafar from Once Upon a Time in Wonderland
Jafar, the evil sorcerer from Agrabah, has his own motives in Wonderland. Having taken Alice’s one true love, Cyrus, captive, he is equally as evil as The Red Queen. Time will tell what Jafar’s true motives are.
The Fresh Prince of Bel-Air
Now this is the story all about how Will Smith’s life got flipped, turned upside down. He plays a street-smart teenager in The Fresh Prince of Bel-Air, who is sent from his West Philadelphia home to live with his rich relatives in Bel-Air. He brings with him his unique sense of style, often wearing colorful prints with matching hats.
Ace Ventura
Ace Ventura may be solving pet related crimes but this detective is breaking more than one rule of fashion. Pairing Hawaiian shirts with striped or plaid pants, Ace’s look may seem unkempt but he balances it out with his finely styled hair.