The number one thing that's helping me make sense of my desire to crossdress goes back (not surprisingly) to my childhood, though it wasn't a fascination with clothes.
Growing up, I was almost always more interested in playing with "girl toys" and watching "girl movies" than the traditionally male toys/media presented to me. As far back as kindergarten, I remember wanting to play more with Barbie than GI Joe. I'd rather play Mall Madness than Risk. My first favorite movie (and still one of my favorites) was Disney's The Little Mermaid. When anime TV shows started to gain popularity in the US in the 1990s, I much preferred Sailor Moon over Dragon Ballz.
Needless to say, almost everyone around me tried to "correct" this behavior. Usually, other little girls didn't mind me playing with them, but the other boys sure did tease me. My mother and my teachers noticed this a lot and repeatedly told me that while it was ok to like those kinds of things at home, I should try to keep those interests there and to myself. While I understand they only had the best intentions in mind, it did make me feel a lot of shame about interests that I had no control over.
Again, I never dressed up as a girl when I was younger nor did I have any extreme desire to do so. My desire to crossdress didn't hit until by early 20s, and only now at 31 have I actually been pursuing that desire. However, I can't help but wonder if those early experiences with "girl" toys, games, and media served as a door to my more feminine side. Even moreso, I can't help but think that all the adults who (intentionally or not) shamed me just for wanting to play with those toys and watch those movies subconsciously suppressed any desire I might have had to dress like a girl too.
So, did anyone else have similar experiences with "girl" toys, games, and/or media?