How Far Will Guys Go For A Feminine Look

[Curt]

I'm just wondering what is too much. I wear high heels, flare pants, fitted tops and coats, concealer, foundation, and a bit of eyeliner, and maybe mascara, very lightly. I like a very glamourous look, very polished. Also long straight hair. Anyone else trying for this kind of look?

[SleekHeels]

I'm with you on the "high heels, flare pants, fitted tops and coats" and long (but wavy) hair... I'll occasionally wear a skirt/dress simply because I really like the look/feel of the outfit, but I find that can be a step too far in terms of people seeing me as "trying to be a woman" rather than a man with a feminine edge to his style. The same with makeup, it's great fun but if I ever wore it in public it'd definitely be very subtle. I also like to accessorise with a little jewelry - a watch, bracelet, necklace and a ring, but not earrings. I'll sometimes carry a bag, unmistakably womens style but usually a practical shoulder bag that's slightly more anrogynous like a satchel (but not an ugly man-bag). I think "too much" is an individual/personal thing that depends on the image we each want to project, and that's different for everyone.

[wetwillie]

Usually I get dressed for the day only to realize later that 90% of the outfit is women's clothes. I don't do makeup and I have a beard which offsets the fem look. I also have shoulder length wavy hair so from the back I may have a femine look.

[Curt]

I think the only guy clothes I have are: a few shirts, ties, socks, and a few coats, and suit jackets, and steel toe shoes for work. All my shoes, boots, jeans, tops, coats, and most of my underwear are womens. And I have to make a correction! I tried eyeliner for the first time, I didn't like it, so I won't wear it. So just foundation, concealer, or corrector, mascara( a little bit on the upper lash) eye shadow, and clear lip gloss. An attractive look, I'm not trying to look like david bowie or anything like that. I just want to look good. I had some gender issues a little while ago that has been resolved. Curt.

[HappyinHeels]

pumpcat, Variations of this question have been asked before but here's my opinion. You've got a myriad of different people here with different expectations. Some just want to wear heels adn that's it. Others mix in a feminine top or a pair of women's pants while others go for women's jewelry or do some makeup or polish their nails. There seem to be many that want to mix a lot more "feminine" things into their wardrobe while not being confused with presenting as a woman. I am happy to be a man but realize there's a feminine side that has to be heard from. I keep my legs smooth and get regular pedicures. I like talking shoes with women as much as I like talking the finer points of football with men. I occasionally dress fully en famme if I have the chance or a social invitation demands it. Each one of us has to decide exactly to what degree we need to express ourselves through fashion as a matter of what impression we want to project. Your life is a journey and this is just one facet of that journey. HappyinHeels

[Lvemadomina]

I don't think what you mentioned is too much. Although I'm not quite going for the look, I do try to push the envelope of what I wear. I'm not much to talk since I've never worn my heels in public, but I feel like I'm getting there. The worst I've done is extremely skinny jeans with Underarmour underwear beneath and a windbreaker on top. But like I said I'm trying to push the envelope in a slow process. Nothing is too much. Well maybe in some extreme circumstances, but otherwise I'm an open minded person and feel what you mentioned wouldn't be a shock to me or anything.

[Foxyheels]

i try to look as masculine as possible hilst wearing clothing normally associated ith women. I'm a bloke but ant to wear what i want not what i'm told.

[freestyle75]

Well.. the question is: How far is too far?

Let's go back 11 years... that's me in 2002, fully dressed:

It felt easier to "pass" as a woman than to be open as a guy and wear what you actually like. I took it too far at that time. Although that is a wig on the picture, 2 years later I had much longer hair (+ extensions + blonde) went out regularly as a girl, but never made real friends. Men would hit on me although I am not into them, women would leave me alone because I did pass quite well at that time, and clubs that would cater towards crossdressers weren't the kind of clubs I wanted to go to. I did dress like I wanted, but I wasn't really myself.

It felt more natural to me to dress this way (got free drinks as well), and I seriously began to question whether it wouldn't be easier to live as a female completely. Started therapy, took hormones, got into huge trouble with my parents, was moving away, stopped hormones, realized that I had been on the wrong path, moved back to where I had stayed at the beginning, put every piece of female clothing in moving boxes, rented a storage place 10 miles from where I live and put the stuff there. Since 2005, I haven't touched it. But I also cannot let go of it. In a weird way, it's a part of me.

I tried to lock away that side of myself, but it came back to a certain extent (via boots & heels) in 2009...

My tummy has grown a bit (from inch size 30/31 to 34), and what is left of my hair is a buzz-cut now. It's also no longer blonde, it's either an ash-blonde color, but mostly grey. I no longer try to pass as a girl, nor do I want to. Stricly no makeup, no nail polish (although I was never fond of colored nail polish in the first place).

I wear all kinds of female stuff, pants, jeggins, turtlenecks, coats, jackets... but I now pay more attention to the way they are tailored. I want clothes that hug the body (still don't like male clothing that is cut way too loose in my opinion), but don't have darts that are geared towards emphasizing women's breasts. All of my (female) coats do not have these typical darts. I even sewed my own fitted trenchcoat, as I couldn't find one that would be narrow enough. That's how I came to sewing my own stuff, which I still do, if I have time.

I always fear that this feminine monster inside of me will take over again, and that I am not keeping the right balance between a more "freestyle" type of fashion and already going too far. The only thing I know is that it will always be a part of me, and that it needs to be controlled, as you can get lost quite easily in it.

[Shafted]

Your feminine monster won't show itself again If you are trying to dress the body which you do have with whatever clothing looks good on it. Putting that stuff away in a storage unit may be a blessing in disguise, as it may just fit the bill of what you want o wear as a guy.

[hhboots]

Well.. the question is: How far is too far?

Let's go back 11 years...

...I always fear that this feminine monster inside of me will take over again, and that I am not keeping the right balance between a more "freestyle" type of fashion and already going too far. The only thing I know is that it will always be a part of me, and that it needs to be controlled, as you can get lost quite easily in it.

Excellent post freestyle and thank you for sharing so much about this private matter. It certainly gives me a lot to think about as I have often debated about how far should I go with the feminine aspects in my life. In fact, in one thread I posted here a while back I remember saying that I sometimes wish I looked more feminine so that I could enjoy a lot more feminine fashions, and that I would probably get very carried away if I could get away with it. i think it was member ILikeKicks who reminded me "be careful what you wish for", which is probably very true.

Anyway, thanks for the thought provoking post.

Oh and as for the picture... wow! If that isn't too wierd and you don't mind me saying so. haha

[ilikekicks]

I say this in humor.. I'd hit that! ;) ;)

[Heelster]

I don't try too. I like my heels although I don't get out enough in them. I'm enjoying my new found womens jeans. They fit better and look better as I see it. Nobody else has noticed that, so it must be working as a 'guy thing'. Let's just say I don't like boxers, and leave it at that. I spend most of my day in what Cintas and Red Wing makes. It pays the bills rather well considering the local economy, so I don't bitch about style, besides, the neanderthal mentality around here has no fashion sense.

[Curt]

Freestyle75. You looked amazing as a girl, if that was your thing. That's the kind of look I'm going for. Do you have any pics of what you look like now. Just for comparison. I know what you mean about the alternative lifestyle bars. Its not my thing either. But I love looking like a girl. Btw, my parents freaked on me with the makeup and heels, if they knew what I was really like, they would be in the hospital with depression. Better off they don't know. Too old to understand. Ash.

[freestyle75]

@pumpcat: Sent you a private message.

[HappyinHeels]

freestyle75, Thanks so much for telling us your very personal story. You really did look quite adorable in 2002 which is an accomplishment. You say that your clothes have been in storage since 2005 and you haven't touched them since as you didn't think you were on the right path. I would say part of you remains in that storage locker as it is a fundamental part of your personality. I think the clothes are an accurate reflection of your personality, after all you bought them. Presenting yourself may indeed be what troubles you the most. The desire to express yourself will never leave you and locking away the clothes only delays the inevitable. Dressing and presenting as you did in 2002 may not be right for you now in 2013 but the clothes could still be worn and enjoyed as a guy. HappyinHeels

[Curt]

I should rephrase the question and take the "guy" out of it. I do a ton of shopping in toronto(were talking about a ton of hours and money well spent), but I've never seen a guy in heels strutting down queen street going into girls stores. A lot of guys with kneehigh boots over the pants but with no heels. A don't know about you guys, but when I go into a store to shop or to starbucks all dolled up in nice clothes and steep heels, a don't do it as a guy, I don't think of myself as a guy. That's just how it is. I don't feel creepy going into a womens store to shop. I feel quite at home. What I'm trying to get at is, are you happy being male but hate that there is no selection or style of clothes you like. Just for fashion and have no disillisions of who you are. Or if you look like a woman then you can wear heels with acceptance, or want to be female and heels, clothes and makeup are just regular things you do. I'm the third one, but it took me years to come to terms with it. I thought there was something wrong with me. You can't change how you feel inside. Now shopping is a lot of fun. So much to choose from. I went into h&m last week. I went into the mens section, it lasted 1 minute, just lame, but I could spend an hour in the womens area.

[Shafted]

I'm the first one myself.

[freestyle75]

@HappyinHeels: True, it's part of my personality, which is probably also why I haven't thrown them away. Those that can be worn as a guy are here in my apartment, but most of the stuff simply isn't intended to be worn as a guy. Apart from that, many of the items have become too small - if I ever manage to loose 10-12 lbs again, I might ... well... let's not speculate. I've bought new skirts & kilts, sewn some stuff on my own that fits much better now. @pumpcat: Put bluntly: as long as you don't want to chop off certain parts of yourself on a constant basis, you are "just" a crossdresser. Which is totally ok. After what I've gone through, I think that some TS would still be living as a guy, if society wouldn't have the rules that men shouldn't be wearing makeup, heels or skirts. I learned that even within the fringe group of crossdressers, there is a pecking order. I might be exaggerating, but this probably makes it more clear: Men in heels look down on men in heels in skirts & pantyhose (too feminine), who look down on transvestites/crossdressers (who put on falsies to look like a woman). Then again, transsexuals look down on transgenders, because TS are the only "real" women (at least inside) and also go through the whole ordeal of SRS, which transgenders don't. Transgenders may still dress quite reasonable (just like regular girls do), while the average crossdresser (whom they look down on) might be motivated by sexual reasons, wearing ultra-high heels, mini skirts and clothes that would make a hooker faint. Yes, I am exaggerating... No matter where you are in this group, you will be looked down on by the average Joe on the street because you are different. If Joe has watched Opera a few times, he might know what TS are, so TS might still be somewhat acceptable, while the casual crossdresser isn't. Opera didn't mention crossdressers, but she showed that TS are acceptable. I think that some crossdressers feel that they would fit better in today's society if they were TS (even if they aren't). After all, we know that being TS is a condition that you cannot change (just as being gay), while being a crossdresser is ... well... unacceptable. If society would accept men who dress like women, have long hair and use makeup, I wonder whether you would still say that you don't think of yourself as a guy when walking into that store. I certainly don't think of myself as a "manly" guy (like this fellow: ), drinking beer, watching baseball games, speaking derogatory about women. But I also don't know whether I am really a girl. Yes, I love all of the things you do, too, and it felt right when dressing up as a girl, but it was also a role that I played, a way to completely let go of the "guy" and become someone totally different. When I go out today, not pretending to be a girl, but still wearing what I like, it feels more "me". Sometimes "me" feels more feminine, sometimes more masculine. I was just wondering whether I am a "happy male". Not really. But I might be if society as such was different. What I am missing most at the moment is a partner. I hope that at some point, I will be able to find a girl that loves me the way I am. I earn enough to be a good mate, inherited the technical skills of my dad (and the navigational skills of my mom = non existent) and can fix the car or a broken pipe, but also enjoy endless shopping sprees and can even sew her the dress she envisions. It seems though that the demand for such men is not very high nowadays. Does it really matter whether people think of themselves as this or that?

[stevey2]

well i like to wear high heels and below knee skirts, shirt ,stockings and lingerie corset or ob girdle when i can I like the feel against my body and the look,its strangely relaxing whilst being sensual but i have never been out in public I recently bought a cheap wig and the long hair looked good, i looked even more feminine and then i dressed it up with a necklace and it looked even better so now ive progressed thurther to the femine side. dont know where im going here but makeup is not an option as tried it once well i think i would need my wifes help with that and im not sure if that would be too much but then again with the right makeup i think i could carry it off......but where would that take me? we all have our dreams and fantasies but problems come when we try to integrate them into reality My wife however can wear jeans/trousers boots, check shirts and no one says shes trying to be a man ? I have seen men dressed so tarty in high heels, big boobs short skirts thick makeup that even makes me cringe but each to their own if they are happy with it The only thing is that look stereotypes the others like myself who may want to look more classy, elegant, feminine thats my view on things