Something I just can't figure out..

I obviously would appreciate answers from people with first-hand experience with this, but this discussion is open to anyone who feels they might know or have something constructive to contribute. But... There's something I just can't wrap my head around:

Why.. if someone is proud to be a man and like other men.. why do they tend to want to dress like women .___. or dress more femininely..?
The point of womens clothing is to flatter or enhance their natural body... so if men are proud of who they are.. shouldn't they want to excentuate what makes them a man?
If they like the colours they can wear pink or purple. It's not like they don't make mens clothes in that colour. Maybe you say that they want to feel "pretty" but pretty is a term for visually pleasing but it's not visually pleasing if it doesn't sit right on the body.
.. So why the need? @_@ And other gays that are attracted to that.. wouldn't it mean that they're attracted to aspects of the opposite gender? But doesn't that defeat the whole purpose of being attracted to the male figure in the first place; the point of being gay?

So yeah.. TL;DR.... why do some gay people like to wear feminine clothing? This question obviously excludes bisexuals and applies to people who are strictly gay.

Umm..
I can speak for this on a personal note considering my boyfriend fits the category to a tee: he simply wants to express himself. While he's glad to be a guy, he also likes to embrace his feminine side by dressing girly to an extent.

My boyfriend also has long hair, like a girl. He says he acts feminine, and he does. I'm very attracted to him because of who he is, though. He's independent, and he doesn't care what people think about him.
And, if I was attracted to him because of what he wears/etc., that wouldn't mean that I'm attracted to females in that sense. It'd simply be.. "Oh, well that's not normal ;)~~~"
Furthermore, just because I'm attracted to a guy with girlish features doesn't mean I'm heterosexual; sexuality doesn't work like that. It's about who you love, and how you love. There are certain..things..that guys have that girls do not and vice versa.

I think some people also do it to break gender boundaries. It's not just homosexuals who break gender standards as well; moreover, heterosexuals who are secure in who they are do this all the time.

Are you a girl who wears jeans? You're breaking gender standards.
At one point in time, it was a taboo for women to wear anything but dresses/etc. Some women to this day still don't wear jeans.
Yet, you do wear jeans because now it's culturally accepted for you to do so.

However, when a guy wears a purse, it's ~such a big deal~ and they're considered ~effeminate~ or ~gay~.
Or..it might also mean that a guy needs to carry important things with him at all times. I carried a bag for a good while that basically functioned as a purse; I'm kind of lost without it. Sometimes you just have to carry a bunch of stuff that you just can't fit in all of your pockets. :/

Before I say anything, I'd just like to mention that I really respect these comments you guys made as pertaining to my question :3 It summarizes everything really well.. but I just want to mention these things kinda like.. to see how you'd approach this argument.

The thing about "Tomboyish girls" isn't that they are trying to select clothing that is particularly masculine, but rather "Gender neutral" items such as a t-shirt or shorts.
Even back in the 50s when the shoulder-pads came into women's clothing, it had more to do for a statement of power rather than a statement of trying to be particularly more masculine, since most of these jackets were indeed paired with skirts, and were cinched at the waist to still create that feminine hourglass figure.
Jeans are also tailored to fit women's bodies.. to show off their round butt and whatnot is the goal for jeans.. and they make separate jeans for men.
But some men, instead of wearing skinny-jeans that are particularly MADE for men, rather wear women's skinny jeans.. this makes no sense to me. I mean.. it'd still definitely be perceived as weird if a woman were going to go around with a penciled-in moustache and chops.. :/

Erik, I totally understand what you're saying. I know it's not always looks that are the deciding factor for who you're ultimately attracted to. But I just find that many gay people that I know go out of their way to bring out their certain aspects of their feminine side instead of bringing it out naturally. (I've seen men in full women's garb.. head-to-toe but who also refuse to shave their long, shaggy beard.. and this just confuses me.) Also, I am curious.. are you saying that you find a sense of androgyny appealing or sexually appealing to you, then? Would you be attracted to a man that looks quite like a man? Or do you feel a lot of gay men are attracted to other men with hints of femininity to them?
:C Also for the record.. I'm not really talking about purses. In some places in europe the "man purse" is actually quite common and accepted, too.. I just don't think it's been properly introduced in other cultures just yet.

Also Pachy, are you saying that some people bring out their feminine side in a way to show that they're special? I mean.. what's wrong with being normal? Your "normal" should be YOURSELF, shouldn't it? Are you saying that in order to feel feminine, you have to wear feminine things?
Does that mean that you're implying that a lot of gay people want to feel more feminine and that's why they dress femininely?
Doesn't that throw the whole point of being proud to be a man and like other men out of whack? @_@ Does this imply that they just kinda.. want to be a girl with a penis? Shouldn't they be proud of their masculinity instead of trying to become feminine?
I mean like.. gender-bender basically means.. wanting to push the limits of their gender into the opposite gender.. but then.. if you associate with the other gender, it doesn't make you gay anymore.
I mean.. even if you have a penis.. if you regard yourself as a woman, and want to be addressed as a woman and make this an ultimate declaration, you then ARE deemed as a woman regardless of if you took pills or did surgery and stuff, and you're not technically gay anymore.

Are you just saying that you feel comfortable in the other clothing? And you just LIKE it? Like.. how if someone likes pokemon that they shouldn't refrain from playing the game just because other people say "you're too old" or something?

Or are you just trying to find a way, ANY way.. to express yourself as an individual? Do you feel like you need to stand out from a crowd? And do you really feel it necessary to get rid of friends who like to associate with your exterior? I mean.. your exterior is still you- or rather, should still be you. Why would you be so tempted to cross-dress? Do you feel that you need to prove to everyone else that you're a feminine person? Do you want to do it because that's the sort of first impression you want to give people?
Are you also gay, if you don't mind me asking? And do you like to appeal to other men by giving some intrigue as to you being androgynous?

I dunno.. Both your explanations helped quite a lot.. because I kinda got to saw two different opinions..:3 So it was really nice and really informative.. but parts of it still doesn't really make sense to me.

I hope I didn't sound offensive in my reply.. but I'm just trying to wrap my head around all of this.. @_@ Please excuse me if I did because that wasn't my intention..

It takes a lot to get from a point where you look at someone and see a "man in feminine clothing" to seeing someone who you feel is "androgynous" and even more so to reach a point where your impression is "female/feminine". There are a lot of different things people pick up on, only one of which is clothing. There's also demeanor/attitude, the sound of someone's voice and speaking style, facial features, and so on. Each one of these things has markers that we're conditioned to associate to varying degrees with the idea of male or female (broad shoulders are quite masculine, long hair is more feminine, and so on). Of course depending on one's viewpoint and experience these might not be the same for two people, but generally speaking a man in feminine clothing is still going to give off a strong "masculine" vibe to a certain number of people. Add long hair, nail polish, and makeup into the mix and that number will probably drop some, but you'll still get people who get an overall masculine vibe. Go to the end of the spectrum with someone who's had hormones and surgery and you'll still find people whose first and constant thought is "man". What I mean to say is that even a feminine guy can have many masculine qualities that someone could be attracted to. (And of course this whole thing can work in reverse.)

As to the idea that gay men are more inclined toward feminine clothing or whatnot, all I can say is that except for one gay guy I know the rest all go for masculine looks in clothing (collared shirts, slacks, vests, and other clothing with masculine cuts and styles), hair styles (short), and so on. Actually, the only guys I can think of who ever wore pink were straight. The one gay guy I knew who was quite feminine was like that while in high school, after which he "butched up" (his term for it) by cutting his hair and letting his facial hair grow.

And anyway, it's also hard to get a feel for someone if you don't know them personally. If you see a guy out in public dressed in something that's feminine you can't really know why he's dressed that way. It could be a common thing or an occasional thing. They could be straight, gay, or transgendered. Or, as I sort of danced around in my first paragraph, it could just a perception that it's feminine and something that other people wouldn't even think of as feminine. It might also be a "man purse" kind of situation where he feels it's quite masculine even if other people might not. Think of how many un-feminine guys have long hair. Even if he does feel it's feminine, it's still only one part of his identity and might be very insignificant to him.

I have noticed among the gay guys that I know that they tend to dress nicer than the straight guys I know. I can't say this is the same for everyone, but it wouldn't surprise me to know (if I could hypothetically get inside everyone's heads) that these gay guys cared more about their appearances in the sense that they took more consideration into how they looked and how they were perceived than the straight guys. If you were willing to accept this as a common (or at least more common) trait in gay men compared to straight men then you might conceivably find at least one reason why some gay men would dress femininely that has less to do with their self identity and more to do with affecting the people around them.

The thing about "Tomboyish girls" isn't that they are trying to select clothing that is particularly masculine, but rather "Gender neutral" items such as a t-shirt or shorts.
Even back in the 50s when the shoulder-pads came into women's clothing, it had more to do for a statement of power rather than a statement of trying to be particularly more masculine, since most of these jackets were indeed paired with skirts, and were cinched at the waist to still create that feminine hourglass figure.
Jeans are also tailored to fit women's bodies.. to show off their round butt and whatnot is the goal for jeans.. and they make separate jeans for men.
But some men, instead of wearing skinny-jeans that are particularly MADE for men, rather wear women's skinny jeans.. this makes no sense to me. I mean.. it'd still definitely be perceived as weird if a woman were going to go around with a penciled-in moustache and chops.. :/

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But that's the point. Jeans became 'acceptable' for women to wear by society's standards.
Men who choose to wear women's jeans have various reasons: my boyfriend, for example, finds it hard to find skinny jeans in male sizes that aren't absurdly expensive that fit him because he's so tiny. D:

Erik, I totally understand what you're saying. I know it's not always looks that are the deciding factor for who you're ultimately attracted to. But I just find that many gay people that I know go out of their way to bring out their certain aspects of their feminine side instead of bringing it out naturally. (I've seen men in full women's garb.. head-to-toe but who also refuse to shave their long, shaggy beard.. and this just confuses me.)

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That's simply self expression. It might be a personal choice, or it might be what they identify with. That's the best reasoning for it.

Also, I am curious.. are you saying that you find a sense of androgyny appealing or sexually appealing to you, then? Would you be attracted to a man that looks quite like a man? Or do you feel a lot of gay men are attracted to other men with hints of femininity to them?

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Personally? Not normally, no. I'm not usually attracted to feminine types, but.. well..
With my boyfriend, I wasn't immediately attracted to him. I thought he was cool and all, and I admired him for who he was, and then..we started talking..and I realized how attracted to him I am. lol. It's more of the personality, and then the appearance, for me.

I'm attracted to all sorts of guys, physically. But, I find emotional attraction is something that you develop in a relationship. Albeit, physical attraction has to be there, and yes, I was attracted to my boyfriend. I think the better term would be: I didn't think he was my type of guy that I was in to.

But, I'm not superficial. Some gay people are. But, just as many straight people are, as well.

:C Also for the record.. I'm not really talking about purses. In some places in europe the "man purse" is actually quite common and accepted, too.. I just don't think it's been properly introduced in other cultures just yet.

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Exactly. But, that's what I'm talking about. In some societies, it's okay for guys to dress like girls and vice versa. But, in others, like American..for the most part, it's rather taboo. D:

My question has always been "Why do other people feel so concerned with what someone else is wearing"? Out of the countless people on this planet there are bound to be some men, gay, straight, trans, or what have you, who will like to wear women's clothing. I understand it's more a question of curiousity, but on its simplest level this is no different than any other recreational interests out there. People like what they like. Plain and simple.