How to shop for women’s clothes if you are a cross-dresser or trans person who is nervous about doing it


The Twittersphere and other online spaces are filled with the agony of male cross-dressers and budding M2F transgender people who talk about their fears in buying clothes for their feminine selves.  These appear to be almost as common as fears of being caught when out “dressed”.  Very early in my life I shared this feeling, but over time it has dissipated, and now it has been replaced by a sense of euphoria and joy.

The purpose of my writing this is not to toot my horn, but instead to hopefully encourage those of you who might still be afraid to allow yourselves to be true to yourself and to let go of shame.

Victoria’s Secret and Online Shopping

I remember way back when Victoria’s Secret catalogue was a new thing.  Such pretty things.  To see those women was to imagine myself as one of them.  And it was a low-risk way to shop.  Catalogue, or online, shopping combined with a P.O. box was a risk-free solution that I had already discovered in high school—no worries about a parent or sibling intercepting the mail, or egads, actually opening it “by accident”.

When Online is Not Good Enough

But there came a time in my life where I wanted the in-person experience.  There were two main factors.  First, I was tired of buying things that did not look or feel like what was in the pictures.  It is not always easy to see quality in photographs, or at all to know what a fabric feels like, or how something will fit.  Practise of course makes things better—we get to know our bodies, but returns are still common—far better to never buy it in the first place.

The other thing was the joy of the experience.  Online shopping just doesn’t feel the same.  Walking out a store with a bunch of bags of really great goodies, all things you know will look dynamite on you, because you just tried them all on, well gosh, there are few things better.  This is the positive side of my addiction.

What’s the big deal?

And then at some point, somewhere along the line in my twenties, I began to resent the social shame.  I didn’t want to feel ashamed that I liked wearing women’s clothes.  I also thought that they suited me.

I remember shopping with two male friends of mine amongst the designer brands in a “deal” oriented department store in New York—many of you will remember the place—Century 21.  I had dragged them to the women’s section, and this was before I was “out”, neither of them knew of my predilections, and in truth, I wasn’t actually cross-dressing in my own mind, I was just looking for edgy, cool clothes.  And then, as now, the women’s section had much cooler stuff.  Jackets, trousers, even some blouses and shirts.  I wasn’t buying dresses and skirts (at least not with them on that day)…and I remember picking out one of the most outlandish jackets, a chartreuse velvet double-breaseted short jacket…it was totally over the top, but it also fit me like a glove.

One friend, “wow that’s outrageous.”

“Cool, eh?” I said.

“You can get away with it,” the other said, a tad wistfully.   And I remember thinking in that moment, ‘you could too, if you wanted.  I just choose to ‘get away with it’.’

And that’s a really powerful life lesson.  If we allow ourselves, if we are true to ourselves, there is no telling what we will get away with.

My Reiki Master did a session with me the other day, and one of the things she said [I’ll blog about the session later] was really germane…”when you live your authentic self,” she said, “you will attract the energy of people who are attracted that authenticity…you will see, you will be a magnet.”

That very night I hopped on a plane in a rather fetching light blue long linen skirt, fun and colourful flats, and long white linen embroidered shirt and a blue shawl.  And I felt great.  After, waiting for the luggage there was a most delicious young trans person with a skateboard, and I am not sure if s/he was pursuing a direction, and was just gloriously inbetween–and his/her nail polish was so dark against his/her luscious and luminous dark-caramel skin, and her/his mother was fussing over his/her clothes in a warm way, and then they were standing next to me, and they spoke to me.

“I saw you on the plane.  You give off the most powerful and beautiful energy,” the mother said.

“Thank you.”

“What you’re doing, what you’re wearing, it looks so beautiful, it works, you look great.”

“That’s so sweet.”

“You’re so beautiful,” said the daughter/son.

“Oh my gosh, you’re so beautiful.  So beautiful.  You look incredible!”  I said to her.

“You’re both so beautiful.  Such wonderful people.”

“Be safe,” she said.

There was more, mostly it was me gushing to the trans girl/boy and him/her gushing to me.  S/he was so beautiful to me.  Is this what trans people do, just gush to each other?  I love seeing my brothers/sisters in this way.

As an aside, is “straight” for a non-binary to love other non-binary?

I think back to my friend, and to all of us who have been afraid or been ashamed, and I think that we create our own “jail”.  I know that many of us live in small towns, or in conservative places, and that people who don’t understand or who do not tolerate can really hurt us.  That is sad.  And I have yet to face this hate [other than through my wife’s struggles to come to terms with accepting that I am trans].

But a small part of me wonders that the reason I am having such a good time with this, the reason I am feeling so liberated, and “euphoric” about being out, coming out, and living true, is that the energy we give out is the energy that comes back.  People reflect back to us what we put out.

Transgender and female spaces and female and male energy

One of the laments that you do see come up on various forums is how sad or hard it is for a trans (I am talking about M2F) person to be in a female space or to be attracted to a woman and then fear (real or imagined) that their transness will be deemed some insidious way of inveigling themselves into a woman’s space.  As if to say that the male energy was always there, was always the motivator.  And I don’t mean to say that this is not real.  Particularly since it is so widely described, but this has not been my experience.

I wrote about coming out during a yoga retreat and how this changed the way that the women I was interacting with related to me.  That was a powerful experience.  But so too have many others.  I have been having the most extraordinarily different interactions with women, and that is by far the best part of what I am living.

Okay, I am not a woman.  I will never be a woman.  In my own mind, and this is for me personally, even if I transition completely, I don’t know if I would ever feel completely female.  I have lived too long in a male body I fear.  But that is my journey, and one that I imagine is different for me than for other trans people.  But as a non-binary person, and in expression of that nature, I am finding that women regard me differently.  I feel that I am not seen as having ulterior motives, that I am not trying to force my way into their spaces or hearts.

In truth, I have long had closer female friendships than male ones…and more of them.  I think in retrospect this was based on sensing that the place I was coming from had a little of both.  But now, as I have come out to my female friends, our relationships have become much more intimate, much more emotional, and so much richer.

Why am saying this in a post about buying lingerie and women’s clothes?  Because it has to do with honesty.  Being true to who we are.  Being seen for who we are, what we are.

How I dress

One of the dominatrixes I admire recently posted online about wigs, and what was our favourite wig…she happens to be into “feminisation” and many clients seek her out for that.  I replied to her that I don’t do wigs, because I feel like they don’t look right on me, and maybe it’s because I have never found the right one, but I like my hair the way it is.  For the same reason, I don’t really ever do makeup—okay a tiny bit—maybe some mascara or lip gloss, maybe painted nails, not the full-on thing…why not?  Because I don’t want to hide.  I don’t care about passing.  I just want to look good…and for me, looking good is being natural.  And as the dominatrix replied, “to each his/her own”…I have to say that she is so right.  There are as many flavours of trans and cross-dressers as there are us, and no way is the right way or more authentic than any other.

What works for me is to find things that I think look good on me, that emphasise or play with my femininity, but in ways that flatter.  I am sure I get it wrong from time to time, and beauty is in the eye of the beholder (or so I said to my wife who asked me who exactly I thought I might look good to).

Gaining perspective at work

I spent two years in retail in the HR department of a well-known women’s fashion and lingerie retailer.  Working the floor was a part of the role as it was for every employee in corporate.  I remember sitting at the conference table in our office, talking over a cup of tea one afternoon and the topic turned to the “dirty old men” who came in to buy lingerie.

It was a fascinating conversation.  None of them knew about me.  They talked about how you can always spot the man who is buying for himself as opposed to buying for a partner.  This became a roadmap for me to begin shopping openly.  Key differences?

The man shopping for his S.O. will almost always ask for help, and will certainly accept it if offered.  The man shopping for himself skulks, looks at labels surreptitiously, may scurry off when approached, or may just say “no thanks”.  When I started doing this, I just began to ask for help.  “I wonder if you could help me find this in a size X,” or “does this style come in pink?”  If I was ever asked “what size is she,” I might know the dress size that was me, or if I was similar in size to the saleswoman, I might say, “she’s about like you.”

But the best part of the conversation was when it turned to the man who was open, who openly said, “they’re actually for me, and I’m wondering if you might help me find something that might work.”  Only one of my colleagues didn’t like that, but the others were all gung-ho, how courageous he is, and various other nice things.  This conversation was a watershed for me.

Shopping far from home

Not getting “caught” before you are ready is another fear to contend with.  The stigma is real.  The fear of the stigma is even more real.  To say it is otherwise would be disingenuous.

Shopping in safe places—“nobody knows me here, so who cares.  Why not?”  That meant cities or places where I thought it was unlikely I would bump into someone who might guess my real purpose.  All of these things helped me build courage, gradually, over time.

Actually, they’re for me

One day I just said, “actually, they’re for me.”  I had reached a point where I was just tired of pretending.  I also wanted to see what would happen.  Part of me was afraid of the reaction, that she would scream or say something horrible and I would get thrown out of the store labelled a pervert or something.  The opposite happened.  She was super helpful and I ended up buying a ton of stuff, some of which I still have, saving it only for the most special occasions.

And it was like a balloon popped.  It was such a relief.  And once I started, the more I talked.  “Hi, I’m looking for something like so…” I might start or just come out with it.  “I’m looking for a g-string, but I need it to be high-cut in the front so it gives me, well you know, a bit more coverage,” and the honesty and openness has always paid off, because it isn’t weird anymore.  When things are natural and out in the open, then it isn’t sick, it’s a breath of fresh air.  [NB.  I am not saying that it is sick, I am saying that we might fear being regarded that way—shame is an awful disease].

Shopping for Clothes more Generally

I find myself shopping the sales, and shopping in stores where I can pay less for nice stuff, and there is always a crowd in such places.  I might be flicking through a jumble of stuff shoulder to shoulder with other bargain hunters, and as the one “man” in a sea of women, potentially competing for the same garments I get lots of looks which are fun to decipher.  And I love to hold something up and ask, “do you think this will look good on me?” or “what do you think?” and I see their faces go from suspicion to acceptance to occasional joy—like we have a shared secret.  I have even had strangers “dressing me” by picking things out that they think will compliment my figure, my body.  And lord knows that lifelong women know this better than I do, having lived it for themselves, and having clothes and body image be so much of the pressure of life…and it is beautiful to be helped, seen, and reacted to in this way.

I remember recently a woman’s face nearly split open with the most beautiful smile when she said, “I love that jacket; it looks amazing on you.”

Tips, advice, joy.  This is what comes with open regard…and this happens whether I am dressed all butch in work boots and construction gear or if I am already letting my feminine side show.  What matters is to not skulk, but to be there fully out, fully me, fully not embarrassed or hiding.

“This is so pretty,” or “you have picked some really beautiful stuff,” the lady [or sometimes man] at the till might say…and I might reply, “I can’t tell you the joy it will bring to wear it.”  I feel the love.  

You want to know how easy it is? Try reading this post on Quora from a woman who works in a lingerie store and encourages the man buying for himself to try the stuff on and just be open. Let’s all lose the fear.

Getting special treatment

I have also found so many unexpected surprises.  The other day I was walking through a parking lot, wearing a skirt and blouse and flats, it was a little dark, and I had too much luggage.  And there were these two men walking towards me.  One of them might best be described as a “good ol’ boy”, and looked a bit rough…and you know what, these ones surprise the most.  He offered to help me with my stuff, and when said, “I can manage,” he said, “are you sure, it sure seems like a lot of stuff.  It’s no big deal, I can help you get it up the stairs.”  And I was left thinking that somehow some of the most dangerous looking men must be more comfortable in their skins.  His friend barely looked at me, but this guy was a real gentleman.

But good things seem to happen all over the place.  At the supermarket a woman plucked me out of the long queue and opened a register for me, and said “come on baby, I’ll take care of you over here.”

And this is just a big part of a general pattern of solicitousness I have found as I have both accepted myself in this way and allowed it to come out.  And this has happened in places and with people that I never would have imagined reacting thus.

Final Word

I would never say, “my way is the way.”    I also don’t want to diminish the risks that may exist for me, or for anyone else that is transgender (and in this case it is for both M2F and F2M)…the fact is that many people find our existence a threat.

I am also very cognizant of the possible toxicity of male energy in society as a whole, that may also be in me or in others, or more importantly, the perception of its existence.  We must be tolerant, all of us—as I must be gentle with those who are threatened by me/us or choose not to accept me/us.

There is this little gem though, which is that when I began to let go of shame and began to just do as I naturally am—it is natural that a non-binary person should wear clothes of either gender, it is natural that a non-binary person is a little bit girl and a little bit boy…and while some people are threatened by it, others love it and respond positively to it.  I choose them, but know that I would have never been offered the choice unless I had taken the first step to reveal myself.  It has been delicious.

5 thoughts

  1. i have been crossdressing for awhile now, i can say when you ask for help. it comes and usually with a smile. I remember going into a Dress Barn about 10 years ago. I saw this dress that was just me in the window. I went in(drab attire) and was immediately approached “may i help you?’ i asked for a size 12 in the dress in the window. She got one and a 14 too said they run small and lead me tot the dressing room. I was nearly knocked over. i was wearing nylons under my pants. She waited and wanted to see them on me. I guess the bottom line is if you don’t ask for help you don’t get it.
    Amazon Prime has a program on some clothes that you try before you buy. I bought a few items that way. nice for closet dressers

    Liked by 1 person

    1. That is wonderful, thank you for sharing. As we accept ourselves, so too does the world. I feel at times that I must, that it is an obligation to those who come after…but the young people of today are so affirming to me. I have so much hope for the world from them.

      Liked by 1 person

      1. indeed the young folks coming out and being who they are meant to be rather than who society tells them to be. It is wonderful. Take it from a 67 year old who has hidden for probably 60 plus years. i used to enjoy Halloween as my Mother always dressed me up in my sisters old clothes. so the message is
        BE proud of who you are and can be.

        Liked by 1 person

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