Help a boy dress up like a girl
August 8, 2008 8:46 AM   Subscribe

I'm a crossdresser - a man who enjoys wearing women's clothes. But I'm rather new to it all, so I'm looking for some practical advice.

So I guess the lack of anonymous reply functionality here might limit the answers I receive, but I thought I'd go for it anyway.

So here's the deal. I'm an average build male, about 5 foot 9, and I want to wear women's clothes (i.e. skirts, dresses). I wouldn't call myself a transvestite or transexual as such, in as much as I'm perfectly happy with the gender I was born with, and I'm definitely not looking to fool anyone into thinking I'm a female. But I do like the feminine attributes of my personality, and I do like the way women's clothes look and feel.

So far, through some trial and error I've managed to work out my basic skirt size (UK 14), and am happy to do some shopping in high street shops for skirts to wear. Beyond that though, I fall down. I'd love to wear a nice dress, but don't even know where to start in regards to shape, sizing etc. Ideally I don't really want to have to artificially change my body shape or disguise it - I'd rather try and find women's clothes that fit me as is. Given the differences between men's and women's average body shapes, is this even possible?

So any advice here is welcome - e.g. how can I work out my dress size, what should I be looking for in terms of getting something to fit, and where can I go to find things to buy? Are there any specialist shops (preferably online) for crossdressers like me? Are there any websites I can go to for more help and advice?

If anyone feels like replying out of this thread, please email . Cheers.
posted by anonymous to Clothing, Beauty, & Fashion (9 answers total) 5 users marked this as a favorite
There are forums at this site and this one. There are an absolute ton of online clothing stores to buy from who would help you out with measurements and such if you search crossdress.

Good luck!
posted by Sophie1 at 9:01 AM on August 8, 2008

One simple approach is trial and error: go to a used clothing store where you can buy dresses inexpensively, bring a bunch home, and see what feels good.

This is assuming that it's impractical for you try things on in the store. If you can try things on in the store, just go for it. But I'd still start with inexpensive purchases until you can figure out what actually feels good for more than the 60 seconds you were an outfit in the store.
posted by alms at 9:03 AM on August 8, 2008

I wonder if you could find a tailor/seamstress who would help you? You might be able to buy clothes that fit approximately, and then get them adjusted to suit.
posted by Solomon at 9:15 AM on August 8, 2008

I believe you can find crossdressing groups via local papers and the internet. A trendy local paper here in Montreal called the Mirror usually has a bunch of ads and personals for crossdressers and other fetishes.
posted by Vindaloo at 9:20 AM on August 8, 2008

Women in general, or certainly hip funky fresh looking ones, know what to wear to accentuate their natural body shape wheather it be curvy or more straight up and down.

You just need to look at athletic girls, those girls who I hear sometimes saying they have boy shoulders and flat chests, Stefani, Venus and Serena thingybob tennisplayers, TP Thomkinson, the more atheletic ones from Trinny and Susanna etc. See what they wear and copy.

Also Gok Wan the fashion god does great suggestion based on body shape on the Dorothy Perkins website I think.

Good luck!
posted by Neonshock at 9:41 AM on August 8, 2008

I know men are built differently than women, but if your skirt size is a 14, a size 14 dress is a good place to start. I like the idea of using 2nd hand clothing to work out your sizes. Most charity shops will have a good selection of high street brands like Next, Wallis, TopShop, M&S, H&M etc.

One thing you will discover when shopping for women's clothing is that a size 14 at Top Shop is not the same thing as a 14 at M&S. Most women know not only what size they are, but what size in what store. I'm a 16 at Top Shop and H&M and a 14 at M&S and Wallis, and I only need petite trousers at Next. So, the 2nd hand shopping method will help you begin to sort that out.

If you find that using the Trinny and Susannah guide you are a column, cornet or goblet, than dresses that drape might be a good place to start. If the dress itself has shape - a gathered bust, an a-line skirt, etc - it will give you the more feminine shape you're looking for without atrificial padding. There are plenty of flat chested women who look fantastic.
posted by DarlingBri at 9:42 AM on August 8, 2008

I think the people recommending the Trinny and Suzannah-style shape guides are right on the ball - male and female bodies tend to be different shapes to each other, but so do any two given female bodies, so the advice should be largely applicable. Apart from that, picking up cheap clothes in a bit of a variety of sizes and trying stuff is the way forward. Since you're in the UK, Primark should be like a beacon of hope and £2 tops.

On the foundation garments, I can relate to a desire not to use them, but once again it's a case of experimentation. You can certainly get a good fit from clothing made for female bodies without any augmentation if you shop around, but whether slipping in a couple of breast forms and a bit of hip padding makes you feel and/or look better is really in your hands. You can grab both fairly cheaply on eBay, so I'd advise giving it a go.

I'd advise caution (to be honest, I'd advise running a mile) in dealing with anything aimed primarily or solely at crossdressers. There are an incredible number of companies out there who take advantage of a small and often furtive market to sell abysmally poorly-made clothes 'cut for the male body' at ridiculous prices, and a similar number of forums whose members have resigned themselves to very low expectations of what they can achieve. Aim to look perfect!
posted by terpsichoria at 10:12 AM on August 8, 2008

Dresses are going to be the toughest, because no, a size 14 skirt does not mean a size 14 dress if you have the broad shoulders of a man. I concur with the advice to go to a thrift store, and try large sizes, and buy an assortment of different kinds of pieces. Stretch is your friend.
posted by Ambrosia Voyeur at 11:08 AM on August 8, 2008

Yes, be wary of those who cater specifically to crossdressers (unless, usually, they are crossdressers themselves); as with any niche market, you're likely to pay more. Of course, a lot of that will depend on how comfortable you feel shopping in 'regular' stores.

You will do better in larger cities, at stores in or near gay or 'hip'/'artistic' neighbourhoods. Don't walk into a M&S in, I dunno, the backwoods of Kent and expect to get understanding service.

At 5'9 you're going to be very lucky; you will fit into the normal range of clothing for women, with some small issues. I'm a fairly small-framed (when I'm skinny) 5'7, and when I did drag the other girls would constantly bitch at me for being able to buy shoes and clothes off the rack anywhere I went. 5'9, unless you're particularly stocky or broad-shouldered, should be about the same. Shoulderless dresses will be easier for you to find a fit from the waist down, stretch is your friend, and a nice bolero jacket can help minimize shoulder size.

And umm.. you're a transvestite. A transvestite is, by definition, a man who wears women's clothing.
posted by dirtynumbangelboy at 12:43 PM on August 8, 2008

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