How to deflect awkward questions when shopping for women's clothing as a man?

Question

This is going to be a bit of weird question, but I don't know how to deal with this anymore.

I'm an Indian guy who's recently immigrated to Britain for college. I'm also very, how to put this, interested in cross-dressing. In India, this wasn't possible for me since I lived with my parents, but a few months ago I decided to take the plunge and buy some Western woman's clothes. These clothes are not for wearing in public. That time and every time since then, no matter what store I go to, I've been asked (by the cashier or clerk most times, or sometimes by other shoppers) some variation of "Who are you buying this for?". Usually, I just pretend to have not heard the question and continue what I was doing, but I'm always extremely visibly embarrassed after such incidents, and in one case, the man who had asked the question kept pressing the issue. Additionally, I often want to try out items in the dressing room (I do try to do this as discreetly as possible), which makes ignoring such questions more embarrassing.

How do I deflect such questions politely and without public embarrassment? I find it distasteful to lie even in these instances, but if it's the only possible thing to do given my circumstances, I would just to avoid the situation.

Answer 1

First things first. There's no reason to be ashamed. Some people may judge you and you may still be judging yourself, but there's really no need to. Love yourself for who you are and try not to let other people get you down.

It may be a little early for this suggestion, but consider trying to become comfortable enough with yourself to be comfortable reaching out to the community. In most major Western cities you'll find like minded people and there's safety in numbers. I know that that may be a big step for you, but finding a shopping buddy will help tremendously.

Many of the trans folks and cross dressing folks I've known find it much more comfortable to shop with a supportive friend and it's always nice to have a second opinion on an outfit that you've picked out. I've been a shopping buddy on a few occasions, it's great fun. Some retailers are even allowing people to join you in dressing rooms to offer a private opinion, so that you don't have to walk out in full view.

If you're not comfortable reaching out yet, you can always just tell people:

Oh, I'm shopping for someone special.

Which has the benefit of being absolutely true and maintaining your privacy.

But I strongly recommend learning to love yourself and trying to reach out. You're not alone and there's an entire community of like minded people out there waiting for you.

Answer 2

I buy clothes for other people routinely. I have never been asked that. If someone in a store were to ask me "who are you buying these for?" I would stare at them in a way that made it clear they were crossing a line, and then say

I'm not asking for assistance with this, thankyou

or

I'm sure you don't need to know that

I would do my very best to indicate (with body language and facial expression) that they have done something wrong and unhelpful by asking that. It is literally none of their business. And I don't mean "I imagine this is what I would do if I was buying cross gender clothes for myself" I mean this is what I would do today, right now, if buying a present for my son or husband and some busybody wanted to know all the details. Like, that's personal and I don't know you.

Now, on the matter of trying things on, that is a harder challenge. Perhaps you could start out by shopping at places with generous return policies. Buy something, take it home, try it on, and if it doesn't fit, take it back and when they ask why you are returning, say truthfully

it didn't fit properly

(The sentence works fine without saying who it didn't fit.) Over time you will get better at picking things out without even trying them on, and you may find particular stores that are more supportive and helpful than others (or just more crowded so as long as mens-clothes-dressed-you goes into the men's change room, they don't care what clothes you take in there.)

Be clear on this: a random store clerk does not have interrogation rights. You are not obliged to answer at all (including lying) just because it popped into their head to ask you. Go right ahead and decline, and if you want to, decline in a way that indicates they were not helpful to ask. And as for the one who "pressed the point" - not a store you want to give your money to, right?

Answer 3

I understand why you would want to deflect these questions. Answering them honestly is likely to incite some weird reactions, if not generate more questions.

From the question it appears to me that you are not (yet) comfortable with that kind of attention, or answering such personal questions. Luckily, you don't have to.

You could respond with something deflecting like "That's none of your business". But that is not very polite, and might even cause them to continue harassing you.

Instead you could just tell them something they want to hear. Remember, you don't owe them anything, you don't have to tell the truth. You could just say "they're for my girlfriend/sister/mother/[insert relative here]". If you do that convincingly enough, that should shut them up.

Alternatively, if you are comfortable doing that, you could spin it into a joke, deflecting it with humor. "Theyre for my pet rabbit" or something along those lines.

Answer 4

So you are asking for a polite response, but the truth is that your reaction should be dependent on the intention of the people you are approached by. There are after all multiple interpretations:

a.) People just want to be helpful. Maybe the clerk only wants to help you in choosing the right sizes. In that case you can politely answer "I'm fine by myself. Thank you." or "Thank you very much. I don't need any help at the moment.".

b.) People just want to be polite and engage you in some innocent small talk. In this case you can answer with a little lie like "That's for my girlfriend. She has roughly the same size as me." - and yes a occasional white lie to a random stranger is perfectly OK.

c.) If people keep pressing the issue, they stop being polite to you and in this case you don't need to be polite any more yourself, too. Here being polite will not be helpful in most of the cases. I would personally just stare angrily at such a person and say nothing at all or say something like "That's none of your business!" or with my best sarcastically undertone "I'm obviously into wearing womans dresses.".

Answer 5

There's nothing I can think of besides walking away that will absolutely stop someone from continuing their line of questioning. Even telling someone you don't want to talk about something doesn't always work.

If you're not interested in lying or offering the truth, one solution is to deflect with an obvious joke and put a question back to them. "For whom are you buying?" I'm in the US, but since you're in Britain you could respond with: "The queen. Do you think she'll like it?" ;)

Making this reply not seem rude is all in the delivery. When I say deflect with a joke, the delivery of the line must match that intent. Look at the clerk with a genuine smile and reply, "It's for the Pope (while still smiling). Do you think he'll like it (light laugh)?" "Do you take cash/credit/etc.?"

You've gotten away from the question you'd rather not answer and put the asker in a similar situation - is that a question they wish to answer? You can then ask them for help or excuse yourself.

Answer 6

The easiest way would be to say you're prepping for a costume party.

It justifies in a very cisgender normative way buying any kind of woman's clothes and trying them on.

You can adjust the character you are going as to adjust for preferences.

Still, buyng in a LGTB area would be a way better bet.

Answer 7

I find it incongruent that no one thinks anything of a woman wearing pants, but the same people raise eyebrows if a man wants to wear a dress. You might feel better if you kept that thought in mind. You are who you are, and your purchase of clothing is an expression of that fact. Even if you don't wear those clothes in public.

In your shoes, I would say that I was buying the clothes for "my sister," or even "someone in my family."

The former would be a "white lie," but the latter is definitely true. You are "someone in your family." This way you answer (truthfully) and deflect the question without "incriminating" yourself.

Answer 8

If you feel safe, try to find the courage to say "myself". Hopefully the shop assistant is just looking to help you find the best clothes, and they can't do that if they don't know who will be wearing them. Maybe they've got some items which would fit a man better.

The success of this is going to depend on the shop and city. I live in Brighton, a very liberal city where it is not unusual to walk past a man in the street wearing women's clothing. There are also areas of London and Manchester with large LGBT populations. People in some other parts of the UK will be less accepting of cross dressing.

Answer 9

If you want to ease into it while admitting that they are for you, and being able to get proper advice etc., you could say “I'm in a community theater production of Kinky Boots and need help figuring out the clothes.” you can be outwardly nervous and they'll see that in-character.

The production earned a season-high 13 nominations and 6 Tony wins, including Best Musical and Best Score …

I've heard my young neice and others singing from it, and people quoting lines from it in the same manner as they use movie quotes. It’s popular and it’s fun. The general public see it in a positive light. “Sex Is in the Heel” became the first Broadway song to reach the top 10 of the Billboard club charts in 25 years, and the cast album won a Grammy.

Furthermore, it’s about cross dressing and a shoemaker who saves his business by going after this market: making “women’s” shoes that fit men, so I thought that was fitting.

So take advantage of the public awareness and acceptance, and ♫ Pump it up!, pump it up! ♫ Till it’s ostentatious ♫

Just a thought.

Answer 10

The obvious, "if we lived in a perfect world" response would be "they're for me." It shouldn't even come up, really, but I'm assuming that you're asking about what happens if you need some assistance from an employee at the store and have to ask or talk about the clothing choices.

If you feel that your town, that store, that employee, or even you, yourself, are not at the point where it is not awkward, since it really isn't anyone's business, I don't think a little white lie is out of order.

You can claim to be buying for a friend or family member. If you are fairly larger than the average female in size, you can claim that this is the source of your awkwardness, nervousness or discomfort - "It's for my girlfriend/sister/mother, but we're actually about the same height and weight...." - where you act slightly embarrassed for them.

Most likely, though, a sale is a sale, and while you may feel like you stick out like a sore thumb, most of your average retail workers are just not that engaged or interested to care if you're buying for you, a similarly-sized woman, or the reason why you are buying it (a quite popular "costume" for parties is for men to dress up like women, though if you were to tell the same person that you're buying for a costume party every week, they might get a bit skeptical).

In any case, hopefully you'll get to the point, soon, where you are comfortable enough with your own feelings that you won't be as worried about what everyone else thinks. Easy to say, by me, a bit harder, in practice, but I hope you get there.

Answer 11

So you, as a man, are going to a store, buying women's clothes for yourself, and you are embarrassed if questions are asked who these clothes are for.

Well, if I, as a man, go to a store, buying women's clothes for my wife, nobody asks me questions. Why? Because the store employees figure out the difference, and while most are decent people and don't try to embarrass you, some are different.

To fix this: You need to change your attitude. Before you go to the store, stand in front of the mirror and tell yourself that you are buying clothes as a present for your wife, or for your girlfriend. Repeat it until you believe it. Then you can go to the store without problems. Allesandro's advice saying "I am buying this as a gift. If the size doesn't fit, can I come back and change it?", that is pure genius. Because no man can be sure that clothes will fit his wife. And you state the "buying for my wife" out there as a statement.

If you buy underwear, well, I would find it a bit embarrassing myself to buy underwear for my wife, so that is normal. Two ways to handle this: For everyday items, look them up on the internet, take a note which item from which popular brand that the shop will have, and which size, and then you go to the store, look embarrased, and show some salesperson the note, saying "this is what my wife wants". Or you are buying are buying a birthday present, or a present for an anniversary. So you go to the store and ask them for advice. You should have the size ready, and you would want something that is nice as a present, but not too adventurous so you don't get into trouble with your wife.

Now let's say you do run into a problem with someone who pesters you and doesn't let go. So what would I do, as a husband buying clothes for his wife, and some idiot salesperson seems to be getting the wrong end of the stick? I would be annoyed. I would be very annoyed. And I would let them know that I'm annoyed. I would ask "What is your problem? Would you like to get a manager here and we discuss your problem with them and then you can explain to your manager why you are losing £150 worth of sales?". Remember, you are buying clothes for your wife. You would be just as annoyed as I would be. And you would answer in exactly the same way. Not embarrassed, but angry.

PS. You can avoid the whole thing by buying online. And if you have nosy neighbours, you can usually get things delivered to some store, or some pickup location. And it's absolutely normal that a woman would order clothes, has them delivered to a store, and then the husband picks them up.

PS. To down voters: 1. The OP didn't mention his age. 2. The OP explicitly mentioned that he was willing to lie to avoid problems. 3. There would be no "false outrage". We are talking about an employee sticking his nose in my private business. The OP would be just as outraged as me. I explained a strategy that works, and why it works.