This also reminds me of a funny story which relates to this very same issue. It's not only MtF crossdressers who have a difficulty in dressing "like a real woman", as you say. Women who regularly wear uniforms for work also tend to have some trouble picking up fitting styles when not on duty. Almost two decades ago, I was drafted for military service, at a time where about a third of my country's standing army were women — most of them having served since they were 18 and pretty much used to wearing uniforms all day long. I had a male lieutenant and two female sergeants training our platoon, and, naturally, they would wear uniforms all day. Once, when I was on leave, and already allowed to go out of the barracks in my civilian outfit during the early night, I suddenly heard my name being yelled at in anger, as I moved out of the camp to cross the street where I had my car parked. I turned around, fearing that I had offended any officer (I was distracted), but all I saw was two gorgeous, long-haired females dressed as very sultry whores, with high-heeled boots, smiling at me. Totally lost and confused, my surprise must have registered, because one of them barked at me with the typical command voice of a female sergeant: "You really didn't recognise us, did you?" And I certainly didn't; only the voice, which was familiar from the daily drills, betrayed the two of them. Well, I certainly was shocked, twice over! First of all, after weeks of drills, I hardly remembered that the two sergeants were technically "female", because, well, that's the kind of thing they make us quickly "forget" while being yelled at. After a while, your mind definitely "knows" that under that uniform is a member of the opposite gender, but one most certainly won't dwell a lot on that point — sergeants are sergeants, male or female matters little in the army, except for separate barracks and bathrooms. So, yes, I had this notion that they would also dress as civilians at some point, but, of course, they were completely unrecogniseable — not with long hair (which they keep tight in a bun under the military cap and which I had no idea how it looked like), lots of alluring makeup, sexy outfits baring flesh and pointing out all those delicious curves. And the second shock, of course, was realising that they were both hotties — who would guess, under a military uniform? — but, well, definitely didn't dress "casually" when going out as civilians: so many years dressing in uniform made them definitely lose all sense of properness in fashion and style. As said, they *did* look like whores — gorgeous-looking whores at that! — and would hardly be admitted at a fancy restaurant or even a high-brow club, which would probably kick them out.

They had some good laughing at my expense, but, after the shock, and when I understood that they wouldn't report me for failing to salute them properly, that small episode remained one of my very few positive moments during the terror of mandatory military service 🙂

Since then, I met a few other women who wear all sorts of uniforms for work, and I have noticed that most of them — of course there are exceptions! — tend to be a bit confused when wearing "normal" clothing. They tend to pick clothes that don't flatter them, or are a few years out of fashion, or either underdress or overdress — or go for outrageous outfits which make them stand out in a crowd, but for the wrong reasons. I guess the same applies to them as well as to part-time MtF crossdressers: we simply aren't used to pick the "right" female outfit, because, well, most of the time we aren't wearing women's clothing at all.

I believe I see your point, made at the very beginning — I keep forgetting that for many crossdressers, the whole point of crossdressing is, well, get laid. This has trickled down to the mainstream view about MtF crossdressing: gender-confused males, who are not quite happy with the label "homosexual" but who enjoy sex with other males when they're dressing as women… because this is so confusing for a mainstream, cisgendered person, they naturally label a MtF crossdresser as mostly a "sex freak" and do not accept such behaviour in public…

When I wrote this article, three years ago, I didn't take that into account — some crossdressers are mainly fetishists, they wear women's clothing because they wish to look sexually attractive to males who have the fetish of having sex with males with women's clothing… confusing, isn't it? No wonder a cisgendered heterosexual is totally lost and rejects that behaviour.

As to the last point, I have to completely agree with you — lack of style definitely raises a lot of eyebrows 🙂 I find myself also guilty as charged — not being a full-time crossdresser like you, and going out mostly late at night, I tend to accumulate much more "going out" outfits than casual, everyday ones. Most part-time crossdressers are not much different. Worse than that, if you're not used to deal with regular dressing, you might not have any clue about which styles fit you, which favour you, and which are simply outrageously out of fashion 🙂 (I get laughed at by my wife when I pick one of those three, and thanks to her, at least I manage to avoid the utter extremes of fashionlessness 🙂 ) So, yes, looking ridiculous is definitely part of the problem.

Obviously there is a very wide spectrum of crossdressers, and you’re certainly on that classification — as are all sorts of guys who might externally be in male attire, but wearing sexy female underwear beneath 🙂

“Crossover” is certainly a first step. In my country (Portugal) there is a starlet who is at the forefront of the crossover style — and he’s certainly absolutely accepted on social circles, TV, and so forth, even if he might not enjoy overwhelming acceptance (but he likes to be provocative in his styles). He actually started his life as a transvestite (he has the perfect face and body for that), but, as he left that way of life and married a rich heiress, he just turned what you call the “crossover” style very public, even though lately it’s hard to classify his style: sometimes he’s wearing clearly female clothing, sometimes it’s a mix, sometimes it’s so outrageous that it belongs to neither gender 🙂

Speaking strictly for myself, there is more fun to crossdressing beyond clothes — it can also go further towards enjoying the pleasure of a whole feminine image and social role — but I fully understand that’s just another spot in the vast spectrum. There is nothing “compulsory” about what you have to do after you start wearing women’s clothes for the first time — just do what feels comfortable! 🙂

You're right — women crossdress all the time, and nobody talks about it as "crossdressing". While males wearing a skirt and some heels, even if the rest of their outfit is still "male", and wear short hair and a beard are… not accepted.

Obviously there is a very wide spectrum of crossdressers, and you're certainly on that classification — as are all sorts of guys who might externally be in male attire, but wearing sexy female underwear beneath 🙂

"Crossover" is certainly a first step. In my country (Portugal) there is a starlet who is at the forefront of the crossover style — and he's certainly absolutely accepted on social circles, TV, and so forth, even if he might not enjoy overwhelming acceptance (but he likes to be provocative in his styles). He actually started his life as a transvestite (he has the perfect face and body for that), but, as he left that way of life and married a rich heiress, he just turned what you call the "crossover" style very public, even though lately it's hard to classify his style: sometimes he's wearing clearly female clothing, sometimes it's a mix, sometimes it's so outrageous that it belongs to neither gender 🙂

Speaking strictly for myself, there is more fun to crossdressing beyond clothes — it can also go further towards enjoying the pleasure of a whole feminine image and social role — but I fully understand that's just another spot in the vast spectrum. There is nothing "compulsory" about what you have to do after you start wearing women's clothes for the first time — just do what feels comfortable! 🙂