It would be impossible for me to say for certain after more than 60 years, but I do not believe the taboo aspect had a significant influence. When I was an adolescent, I was drawn to some trendy and maybe even avant-garde styles that were not generally worn in my family and social circles. These were not always feminine, but more decorative than functional and drew more attention than what might-have-been standard attire. Two examples that come to mind are wide belts buckled on the side and penny loafers. My mother actually bought me some penny loafers as part of our annual Easter go-to-church ensemble. But then she hid them away until Easter so they’d be special. The wide belt thing was something that was emblematic of a sort of tough guy persona – think West Side Story! I borrowed a wide belt from a classmate and began wearing it somewhat covertly.
Why are either of those significant? Probably because it was a sort of fetish perspective on clothing that was new in my life. I regard these as the origin of my fascination with the feminine. Over those early years, I’d try on items that belonged to my mom and sister, but not very often or, in fact, not very compulsively. Then, I went on with my life, school, the military, career, marriage, and parenting. Through this period, I frequently choose underwear, clothing, shoes, and accessories that fit with youthful styles. In those years, men unabashedly wore hip-huggers, flares, shirts-like-blouses (The Monkees), bikini underwear and swim suits, high heeled shoes, and all sorts of jewelry. So, although some bemoan the judgments of the past, the 70s was pretty liberating for crossdressing inclinations.
I sold real estate part-time early in LE career. I could/would wear some pretty over-the-top outfits and, aside from occasional comments, it did not appear that many disapproved. I had a jeans suit, with flared bottoms, belt loops that would accommodate a wide belt, and a vest. I generally wore a silky (blouse like) shirt with an enormous collar. I had several pairs of high heeled shoes in assorted colors – black, brown, tan, and white. I had some high heeled knee-high zipper boots that I usually wore under my flares. I was pretty trim in those years, so I occasionally wore hip-huggers with a crop-top and a bare midriff. The midriff thing kind of stretched the envelope, but it did not generate immediate reaction or disapproval. One of my favorite purchases was a brown knit jumpsuit that was body hugging down through the hips and flared at the legs. It had a with belt made of the same fabric with a square brass buckle. Partly because of Elvis and some other performers, men’s fashion jumpsuits we’re out there for a moment. But they didn’t catch on and I could not find another.
So, what am I getting at? Well, I think this was a snap shot in time when men could wear women’s styles. It didn’t last, but it was exhilarating and satisfied most of my need to crossdress. My answer to the taboo thing is that it is not part of my motivation. I like wearing women’s or androgynous styles. I really do wish I could do it all-the-time and just-be-me!