Advice for a young woman interested in cross dressing?

October 25, 2010 8:59 AM

Are there any bars or similar in the Boston area where a 21 year old female could go dressed as a man? Are there any stores that would be willing to rent a tux to a woman without asking too many questions? Other questions about cross dressing inside.

I've never (for as long as I can remember) been 100% comfortable as a girl or woman but I haven't felt quite uncomfortable enough to warrant coming out as trans/genderqueer/etc. I do enjoy wearing men's clothing, particularly dressy men's clothing. It occurred to me recently that cross dressing on the weekends would be a good outlet. Does this seem like a good idea? I hear about men dressing as women but not much about the other way around. Where can women go to dress as men?
If you have done this, how did the logistics work? Did you feel comfortable riding public transportation in drag, or did you find somewhere to change? Boston seems pretty liberal but it only takes one backwards asshole to make me a victim of a hate crime. How did you explain where you were going to your friends/roommates/family? Does the fact that I'm pretty sure I'm attracted only to men add any more complications?
Any other advice about female cross dressing is also welcome.

posted by anonymous to Grab Bag (19 answers total)

I do not know the answers to most of your questions, but to get yourself a tux or other formal clothing, sold to you by people who actually know what they're doing, at a price that will not make you crazy, I'd suggest Keezers. Go buy a suit/tux and then spend the money you'd saved getting it altered to actually fit your female form. Women wearing tuxes is not so crazy and I've always gotten great service there.
posted by jessamyn at 9:01 AM on October 25, 2010

Come to gay/trans/bi/queer events! Then you'll fit right in, and see others wearing hot menswear too! The best advice to find some events is to get on the Boston Queer Agenda. They send out weekly emails of upcoming events. I guarantee that nobody would bat an eye at you wearing a tux or suit or other menswear to any of the events, especially if it's suitable attire for the occasion. A tux at a queer coffee at 10am on Saturday morning might be a bit out of place, but people would be welcoming and excited, not perturbed! There are oodles of dances, fundraisers, drag shows, burlesque events (where you in a tux would be hotly welcomed!), dinners, walks, coffees, discussions, etc.

Even if you don't really want to flirt with anyone there, or identify as queer/trans/ you will certainly fit in. Queer folks know you can cross-dress without any indication of sexuality or attraction. You probably will get folks hitting on you, but just talk to them and make some new friends! Congrats for figuring out a new direction. I know it's bold and brave and scary and also intoxicating. Halloween is coming up and there will be a number of queer events -- you will be so hot in a tux!
posted by barnone at 9:08 AM on October 25, 2010

I think pretty much anywhere in Cambridge/Somerville/JP no one would bat an eye (and I'd venture that you'd hardly get noticed in Boston, either, particularly if you stay away from the North End/North Station area, places around Fenway when the Sox are playing etc--though I highly recommend that everyone stay away from those places all the time; they're often filled with boorish folks). I have a couple of women friends who basically just wear men's clothes (tie, button down shirts, blazers, the works)--I think they're all Somervillains.

Also, if you wanted to show up in formal wear of any stripe, you'd be a hit at next season's Derby Dames bouts. I can't imagine anywhere in the Boston area you could find a group that would make less of a deal about this than the roller derby.
posted by Admiral Haddock at 9:14 AM on October 25, 2010

I can't say I have any experience in personally cross dressing, but I've known a number of trans-persons that were close to my heart. The best advice I can offer is to start slow. If you feel that bringing clothing with you and changing is best, go for it until you feel comfortable riding the metro in full gear. For example, you could try to wear something that was more symbolic of masculinity at first. Or perhaps just a few items to see how you felt. Ease yourself into it and be aware of your own comfort level as you progress. While one backwards asshole could indeed try and bring you down, the more strength you have that this is another beautiful facet of who you are, the less any nonsense will affect you. For an example of a woman wearing dressy men's clothing, I suggest Janelle Monae. She can really rock a tux.
posted by Vrai at 9:16 AM on October 25, 2010

Also: for your googling efforts, you might want to search for "FTM dressing" or "ftm clothing" or "butch clothing" -- ftm stands for "female-to-male" and while you might not identify as that, it's a community of folks who deal with how to dress in more masculine attire with female bodies. You might never identify as FTM but just want to cross-dress at times, which is more than okay - but it'll give you some hits on tips and styles. Butch is one identifying term given to more masculine (gay/queer) women. Most (or many) butch women don't identify as men -- they identify as masculine/butch women and many wear exclusively masculine or men's clothing. Again, even if you don't identify as queer or butch, it'll give you a wealth of links and visual inspiration.

If you're curious about FTM or even the whole concept of women/females dressing as men/males, or the whole idea of masculinity in general, Female Masculinity by J. Halberstam might be an interesting read for you.

Feel free to message me for any other questions or for better ideas. I am running out the door and will try to post more later, but I'm totally open to chatting about any aspect of this. Many of my close friends are FTM and trans, and I'm as queer as they come. Privacy guaranteed.
posted by barnone at 9:18 AM on October 25, 2010

Agreeing with Admiral Haddock--you could come to my church in Cambridge every Sunday morning and no one would bat an eyelash.
posted by Melismata at 9:20 AM on October 25, 2010

You might try Club Cafe near the South End as a queer-friendly gender-flexible place. But, yeah, you could totally hang out in most of Cambridge and be pretty comfortable. Also, you might add "drag king" to your list of searches.
posted by ldthomps at 9:31 AM on October 25, 2010

Google 'boston drag king' and find shows and events where there are women performing in male drag. And then put your clothes on and go. Have fun!
posted by elsietheeel at 9:35 AM on October 25, 2010

All the King's Men rock like a particularly rocking hurricane.
posted by Sidhedevil at 9:37 AM on October 25, 2010

And on preview, following right up with Sidhedevil: Nothing like short notice, but if you are free and can make it to MIT tonight, there's a free public showing of Play in the Gray, a documentary about All the Kings Men. There's supposed to be a Q&A with the director afterwards, and the event's sponsors might be able to connect you with other resources.
posted by sigmagalator at 9:38 AM on October 25, 2010

I doubt a woman in a tux (or other formal wear) is even going to come across as a cross-dresser, the way a man in a dress will. You're going to look like a woman in a tux. Or if you really go all drag king, an androgynous man in a tux.

Everyone looks good in a tux. That's sort of the point of a tux.

Women wear so many men's clothes these days -- jeans, t-shirts -- you're going to have to really work to dress like a man, and not a woman in men's clothes.
posted by musofire at 10:04 AM on October 25, 2010 [1 favorite]

I know women who've rented at Keezer's without an issue, and most other chain places without any problem, too.
posted by rmd1023 at 10:05 AM on October 25, 2010

If you go to a tux shop to get measured in the next week, you can say it's part of a Halloween costume. Once you have the measurements you can use them to rent any time you want without getting hassled.
posted by miyabo at 10:11 AM on October 25, 2010 [2 favorites]

When I was in college, I rented a tux for a formal. I was well-received at the the shop, all the men and told me how good tux's look on women, especially ones with tails. This was 15 years ago in the South. If I got a good reception then and there, I'd imagine you probably won't have much of a problem with it where you are.

Also, to repeat what someone else said, women can really get away with wearing men's clothes. If I'm not at work (and even sometimes when I am) I'm in clothing designed for men. It's really not that out of place, women have much more flexibility than men do. With all the opposite-gender clothing I wear, if I were a man, I would definitely be labeled a cross-dresser.
posted by Tooty McTootsalot at 11:36 AM on October 25, 2010

I'm a straight woman, but I like wearing some men's clothes for the cut and style. A lot of the time I get better quality and fit for a lower price in the Mens or Boys department. I know I am by far not the only woman who does this.

I don't think you'll have a problem shopping in Mens stores at all. I never have, and I've shopped in lots of different kinds of mens stores. If you act like there is nothing wrong with what you're doing nobody will bat an eye. The salespeople I've worked with have always been friendly and helpful whether I'm shopping for myself or my husband. I've even shopped at Farm Supply stores and nobody cared that I was trying on jeans from the mens department instead of the ladies.

P.S. I had a friend who wanted to wear a tux to prom. This was 12 years ago in the Phoenix area and she said that she wasn't close to being the first woman they'd fitted. I don't think you're as isolated of a demographic as you think you are. Marlene Dietrich made it fashionable for women to wear tuxes way back in the 1930s.
posted by TooFewShoes at 11:42 AM on October 25, 2010

You'll have absolutely no trouble at Keezer's. Promise.

Also check out Truth Serum events and go and wear your tux!
posted by jdl at 11:47 AM on October 25, 2010

Gay woman, dress in mens clothes daily. Though I don't *try* to pass. I often do pass, which is hilarious in it's own right.

There is nowhere in Boston, save possibly some shops in Southie, where a woman buying a tuxedo or suit would raise an eyebrow.

Likewise there are few places in the area where a woman wearing one would raise an eyebrow. Now, trying to pass as a man is an entirely different thing. I have been on the receiving end of some very aggressive behavior from some men who felt that I was trying to pull something over on them even though I was not trying to pass - my referencing "girlfriend" reinforced what they saw as my masculinity. You see?

If you really are struggling with gender issues I'd encourage you to seek advice/help there. Who you are attracted to has little to do with your gender. I know several trans guys who were attracted to women when they lived as their chromosomal women selves but as they transitioned they found they were actually more attracted to men and live as gay men now.

MeMail the hell outta me if you want to talk. Also - will be in Boston some time before Christmas if you'd like to have company on some gender bending adventure.
posted by FlamingBore at 11:51 AM on October 25, 2010

Ooh, ooh! jdl's link informed me that there was a TraniWreck show on November 21!!1!

I know that you're anonymous, anonymous, but a) come to the show if you can because SO AWESOME, and b) if a handsome person in a dinner jacket says "Plate of beans" to me, I'mma know it's you and be delighted.
posted by Sidhedevil at 12:25 PM on October 25, 2010

Thought of this thread again today when I was waiting for the T at Back Bay and a young woman dressed in a man's sweater, with a collared shirt, tie, and sort of men's cut khakis was also on the platform, and no one cared--except for me, as I happily crowed to myself what a cool, tolerant place Boston can be.

Be yourself, and have fun!
posted by Admiral Haddock at 8:32 PM on October 26, 2010