The ’90s were rough on men’s fashion. Case in point: when Will Smith wore baseball shorts, socks and sandals to the Playboy Mansion to meet Hugh Hefner. His Fresh Prince of Bel-Air co-star Alfonso Ribeiro didn’t fare much better, unless of course it was a pajama party rather than a pool party, because at least then his boxer shorts/swim trunks would have been technically ok.

Karyn Parsons on the other hand, looked stunning as she always did back in those days.

There’s a lot going on in this picture, but let us never forget. Never forget what men wore in the ’90s. Never forget where Will Smith started from. And, inversely, never forget how long Hugh Hefner has been the man.

Will Smith Wore Baseball Shorts

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