She staged one of Roland-Garros' most memorable upsets in 1989 when she -- a 17-year-old outsider -- beat World no.1 Steffi Graf.
She was the youngest player in history to win the tournament, at the time. Vicario went on to become the World no.1 herself, winning four grand slam singles titles, six grand slam women's doubles titles, and four grand slam mixed doubles titles.
Having become a mother in 2009, the 44-year-old has gone through many style transitions, but a few moments stand out for her in particular over the years.
Speaking in an exclusive interview with CNN Style, she recounted these memories and spoke of the differences between tennis style now and during her era.
"When I look back at the clothing, compared to now -- it has changed a lot. The materials, products, everything...we didn't have a lot of choice. Now there is a lot more choice. The transition is natural, but it is funny to see the images from 20 years ago to now."
"I wish I would have had the beautiful, lighter clothing that exists today. Now if you feel like running, it's so light."
So who does she think was the most stylish tennis player of her time?
"In my era Steffi Graf was my biggest rival, but she was very stylish. A great player and very beautiful. Anything she wore looked good on her."
And what of her own style -- did she ever feel pressure as a woman on the courts?
"When I was playing I was wearing what I was wearing because of the sponsor, but afterwards I was able to show the people my personality.
"I always felt comfortable on and off the court."