1992. Cross dressing women explain why they enjoy men’s clothes and when they wear them

October 8th, 1992. Geraldo Rivera on his namesake talk show brings us ‘Women who dress as men’, this introductory segment hearing from the guests.

“Ever since I was very little I felt like a feminine girl, and I also was a tomboy….and I think it’s part social also because I was rewarded for looking pretty, and feminine…”

The women describe how wearing clothes usually used by men helps them express who they really are. Some are trying to emulate the look that they like, but only doing so part of the time. Most are married and talk about reaction from their partners.

Our host mentions Phil Donahue frequently discussing cross-dressing men, but this may be the first feature discussing cross-dressing women.

In 2025 forms of expression have gone far beyond different types of clothing.

This day, Geraldo’s television history.