So what makes me choose the clothes I wear when I go out looking feminine?
There are certain practicalities to consider (hiding the engineering works required to fake up my cleavage, how much walking will I do, will I be likely to need to take a toilet break, that sort of thing), which rules out a lot of great-looking stuff (halternecks, strapless or backless dresses, mostly – this is really annoying).
If I want to pass as feminine (at least on first glance, and until I start speaking), then I don’t want to wear unisex stuff – I can wear jeans, trousers, ordinary shoes or trainers, shirts and what-have-you as a guy. Normally I’d never show off my legs or expose my chest, but I have no problem wearing short skirts or showing off cleavage (one of these days I’ll explain how I do it).
Part of the attraction of cross-dressing is wearing stuff I wouldn’t normally wear (it’s not a lifestyle thing for me; it’s more of an occasional social thing). Because this isn’t a lifestyle, I’m not keen on spending too much on it; I’m a charity-shop transvestite (which has the advantage that if I buy something the wrong size, at least I haven’t wasted vast sums on it).
I want to wear something that looks good, but not overly glamourous. I usually want to dress to fit in, rather than stand out too much: flared skirts or dresses, flat calf-length boots, cardigans. My legs are a battlefield, so I’ll wear tights or leggings rather than leave them bare; I found thick flesh-coloured ballet tights can cover up a multitude of sins…
Occasionally, I might want to show off. It’s a bit of a circular argument here. I’ll see a dress I think looks great, but only because it’s tight and really flatters the mannequins in the shops. So I’ll buy it and discover I’m too damn lumpy and flabby to pull it off. I then spend weeks or months losing weight and practising tucking everything away until I think I can wear it. By this point, I think I’ve earned the right to wear the damn thing, and am prepared to put up with all sorts of discomforts to wear it. (This also applies to certain fancy dress items; I think if I’ve been out and about often enough dressed in everyday female clothes, then once in a while I can try out something a little more extroverted.)
So that leaves a huge range of things to sift through, and throws up a few issues most guys might not even consider. That’s a topic for my next post, though…