Wednesday, September 15, 2010

The Pains of Cross Shopping

A question I sometimes get, usually from other dressers (especially those starting out) is "what's the most agrivating thing about cross dressing?" Oh there are a number of things that are up there on the list: body hair removal, lack of hips, maintaining wigs, etc. But probably the single biggest hurdle for the average cross dresser is clothes shopping. As an added twist for every picture I put up in this post I'll be saying where I bought what I'm wearing. As much fun as shopping can and should be there's a whole litany of reasons that most cross dressers dread it. The biggest problem for most dressers is simply one of fear, cross dresser are usually highly paranoid about being discovered. Even those who don't consider themselves to be closeted can be shaken at the thought of going into a store to buy women's clothes. The funny thing about fear in this situation I've learned is that it's almost totally unfounded. Unless a dresser actually does something to indicate otherwise virtually all sales-people will assume a man buying women's clothes is buying for a wife or girlfriend. Even if they have a slightest incling of the true nature of the shopping trip there's two things that dressers need to remember: 1) Odds of seeing these same sales people ever again is pretty slim in most cases and 2) As long as money is being spent the sales people really don't care who it's for.

Shoes from Steinmart, pants and shirt from Rainbow, hair from Ricky's NYC and Photo by Laura

The fear and annoyance of store shopping results in most dressers doing their shopping online. This only solves the problem of fear in a public setting, but it brings a whole list of other issues. The big one is the problem with all online shopping, especially for clothes: you can never be 100% certain of what you're getting. Pictures can be deceiving, lighting of a photograph can affect how a color looks on the computer, and sizes are even more guess work than usual. Finally returning something that was mailed can be even more of a pain than returning to a store. That said many of my favorite clothing items are online purchases. My beloved platform boots were one of my early online buys. Same goes for my saloon girl skirt, my silver one piece and my breasts. Yes that's right, my tits came by mail. Hand delivered with care. My most recent purchase made online was a t-shirt from Nic Buxom's online store. Sometimes there's just things you find online that can't be found locally. However I would highly advise against any dresser from ordering wigs online. More than any piece of clothing you can buy a wig can look completely different on different people, and you really need to try them on. If there is a wig shop in your area (or a costume store with a decent wig selection) I promise you they've already encountered dressers and will be understanding and respectful.

Shirt from Nic Buxom, corset from Amazon, hair and cuffs from Ricky's NYC, collar from Fetish Flea Market, garters from Tic Tac Toe, lahes from Old Gold and Photo by Laura

Even if or when a cross dresser gets over their shopping fear enough to actually buy a few things that starts a whole new area of issues: understanding the sizes. Men don't understand how good they have it when it comes to clothes sizing. Take pants for instance, men's pants have two measurements: waist and length. In men's pants I'm a 31"x32", that's my size and that's what I look for. It all makes perfect logical sense, and it doesn't change no matter what kind of pants I buy. Women's pants are assigned a completely arbitrary number that isn't even consistent from brand to brand. So in women's pants I'm anywhere from a size 10 to a size 14. Sadly trial and error is really the only way to get it right and even the most daring dresser probably won't take women's things into the changing room at the store. That means dressers have to take it home before they can find out if it fits or not. The one exception to this is in a costume store, where men interested in women's items for themselves doesn't really raise an eyebrow. However dressers who want a more casual look won't find what they want in stores like that.

If there's one thing a cross dresser likes more than a good buy it's free stuff! Dressers and queens love is a good give-away, such as the one Olivia Rouge is currently having. There's nothing better in the world that getting something pretty and sparkly for free! And of course for the timid the "it's for my girlfriend" ploy works even better in this situation, because what guy wouldn't try to get a great looking gift for free?

Shoes from Payless, shorts from Rainbow, shirt and necklace from Steinmart, bracelet from Clair's, hair from Ricky's NYC, Photo by Stacie Joy

In NYC I had gotten to the point where there were a few clothing stores I would make semi-regular stops at. Now being in Vermont I have to start over and honestly be a little more careful. In huge city like New York nobody cares and even if they do you won't see them again. In more rural areas there's a distinct possibility of running into that store clerk on the street or that you might know some of the same people. This means that from now on most of my in-store shopping is going to be done further from home. I'm always sure to stop into Old Gold when I'm in Burlington. I'd done a little shopping at the local Fashion Bug but they went out of business. I was also forutnate enough to have Laura come with me on those trips. Which brings up another thing for dressers. If you have a female friend you're out to bring them along when you shop, it should help get rid of that lingering fear because everybody will assume you're buying for her. I think that's about it for this little ramble. Hopefully folks have found it insightful/helpful/amusing or at least it killed a few minutes that you could have been doing work. I'm so bad for productivity.


  1. Really a fantastic blog piece. This is an issue that comes up in one way or another in almost every conversation I've had with dressers I know. Love your blog, keep it up!

  2. Thanks Denise. It's definitely a big issue for many dressers, but they tend to psych themselves out half the time. Half of it is confidence (walking into the store), the other half is trial and error (sizes).

  3. I agree with everything you're saying. One thing about the sizes though is that when it comes to online stores, they usually got those neat size charts. You measure your chest, waist, legs etc.. And that usually helps to narrow down the sizes to a general area at least..

    But, as you say.. It's trial and error. Often (as a man) you need larger sizes on tops and clothes above the waist, because of broader shoulders and wider chest. And since you have a narrower waist, skirts and pants might need something smaller.

    But if you get the courage to buy everything in stores, and try them on before you buy them. Then pretty much all the problems are solved. It's really just mind-games. Play it right, and you're the winner.

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