Glamour salutes the winners of their Top 10 College Women Competition in the June issue, a tradition they began back in 1957. When we heard that Martha Stewart was selected as one of the honorees in 1961, we had to investigate--and we're glad we did.

In honor of the 50th anniversary of the competition, Glamour.com put together a snappy slideshow with retro fashion flashbacks and informative anecdotes about how much we women have changed and, in many respects, how we've happily remained the same. A few highlights...

• Originally called “The 10 Best Dressed College Girls,” the contest's winners were chosen for traits such as “impeccable grooming” and “shining, well-kept hair.”


• 1968 winner Katiti Kironde II of Memorial University of Newfoundland made history as the first black woman to appear on the cover of a major women’s magazine.


• In 1969, the contest's focus shifted from fashion to overachieving, er, academics and leadership. In 1977, two honorees modeled the "perfect" college wardrobe—a far-cry from the sweatshirts and flip-flops that so many co-eds toss on today.


• Sheryl Lee Ralph was a 1975 winner who went on to star in the original Dreamgirls on Broadway.


• For the 1996 photo shoot, all the winners wore the present-day pariah of the fashion world: Mom jeans, in all their high-waisted, tapered leg, stone washed (or classic blue) glory.


• Former winner and novelist Heather Cochran shares this advice for younger generations: “Don’t be afraid to fail—well-told tales of spectacular risk and enthusiastic failure make for very good party conversation.”