The NBA draft lottery used to be a quiet, almost quaint affair, with talented and hopeful college basketball players vying to be chosen by a big-league team, with the potential of a long, lucrative professional life ahead of them. And most of these future superstars wore unassuming—if a tad ill-fitting—suits, gawkily posing with their future coaches.

How things have changed. Today, like so many other once-niche, insidery affairs, the NBA draft has exploded into a highly-publicized, closely watched spectacle—and the players have stepped up their fashion games accordingly. Take last year’s installment, which featured designer labels, sharply-cut suits, wild swings (pleated shorts!), and plenty of bling (including pearls and Rolex watches). After all, these guys have to prove that they’re worthy of the tunnel walks that are in their future.

Still, looking back on the NBA drafts of yesteryear, one can’t help but feel a touch of nostalgia for simpler times. Of course, we now know how these guys’ careers play out—glory, fame, success. Soon, they’d have the means to wear any designer they like, but catching a glimpse of them in those boxy blazers, too-long pants, and questionable neckwear serves as a reminder of how far they’d travel to get there. With that in mind, we’ve gathered the NBA draft lottery looks for some of basketball’s most legendary VIPs—wacky, charming, slightly embarrassing, but altogether a good time. Take a look.