Even though his style and his skills have deteriorated with age, Derek Jeter was quite crispy in the '90s as a young superstar who brought glory to New York. Off the field, he perfected the t-shirt under the blazer look, a trend that began in the '80s but lasted well into the next decade. His boxy blazers were the fit du jour, and the toned down dressiness that he perfected certainly helped him reach every base a few hundred times.

Take a look at a line-up of Hollywood's finest women from the '90s and chances are Jeter knows all of them in the Biblical sense. Though being a millionaire athlete in NYC certainly helped, it's doubtful that the country's fashionistas would've hooked up with Jeter if his style wasn't on the same level as theirs. What young actress/model/singer wants to share the spotlight with a slob?