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Answer by Tamara Wiens, I am happy now:
Being transgender can present some particular challenges when shopping for clothes, particularly when first starting. In general, I would say that, unless you are in a jurisdiction that has laws and penalties for being in the “wrong” bathroom, change room, etc., just do it. If you are in a situation where you are going to transition to full time, you need to start doing it sooner or later, and as others have said, it can still be nerve-wracking after you are full time. And if you plan on ever going out in public “en femme,” even without transitioning, the same argument applies.
The thing is this: In department stores in particular, there is very little scrutiny: Women come in all shapes and sizes, and there are lots of men browsing through, either idly waiting for their female companions or because they think that they can buy them something, or whatever. More generally, in public, very few people actually “see” anyone else—the last time you were in a store, can you recall more than a handful of faces that you encountered? Unless you are blatantly not fitting in, most people won’t notice you at all.
As for the change rooms, you have two strategies. The first is to take your selections to the change rooms of whatever gender you are presenting as while you shop and show as little as you need to of the items that you have (if you’re at the men’s) and try them on. The second is to boldly go to the women’s, where you can get an employee to get you another size of the item when needed, if you are in a women’s clothing store. If you get any grief from the change room checker, ask to speak to the manager on duty—most managers realize that the satisfied customer is a repeat customer and don’t care what color, gender, or orientation your money is, just that you spend it with that store. Some of them are stupid and don’t think about the fact that a satisfied TG who feels “safe” will spend hundreds or even thousands of dollars on clothes. (I’ve spent close to $10,000 in the last 18 months, building a professional woman’s wardrobe from scratch.) In that case, shake the dust off your shoes and politely let him or her know that the store will get no more of your trade, ever, and that you will publicize its intolerance. In one of the happy jurisdictions that prohibits discrimination on the grounds of gender presentation, you can even sue or threaten to sue—but that’s much more fraught, as you will have to come out publicly to do so.
A few hints, learned expensively:
When buying clothes, don’t buy anything if you don’t love it on the rack and equally love it when you try it on. We often fall out of love with an outfit that we used to like; we rarely fall into love with an outfit that we didn’t originally like.
To save time and avoid buying something that just won’t ever look good, take the time to figure out what styles work for your body type and what don’t. If you are carrying extra weight, form-fitting styles have a tendency to emphasize all the wrong bulges. If you have broad shoulders, then square-cut shoulders make them look broader. If you have big feet, then wide-bottomed legs on slacks make them look smaller, and so on. There are online sites and in-person courses for all women on buying to suit your body shapes.
Buy styles appropriate to your apparent age. This is important. I look 10 to 20 years younger than I actually am, so I can get away with clothes that would look somewhat silly on another woman who looked my actual age. One thing that too many of us do is try to be “sexy” by wearing miniskirts and crop tops, or by wearing the fashions of our own teen years. While that is a fashion statement of sorts, it will likely get you the kinds of attention that you don’t want. Discreetly look at the clothes that women your age are wearing and buy similar fashions, and you’ll blend in just fine (if that’s what you’re looking for).
Bottom line: If you want to do it, eventually you have to do it, and there is no way around having a “first time” shopping for your preferred clothing, or en femme, or what have you. And, as with any first experience, it will be scary and exciting and embarrassing and fun and so jumbled up that you will likely only remember bits and pieces of the experience. Have fun, and good luck!
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