Q: How hard was it the first time you wore women clothes in public and went shopping for new clothes or did you just do everything online?

How hard was it the first time you wore women clothes in public and went shopping for new clothes or did you just do everything online? did everyone just stare at you and say freak or nasty comments. I just don’t know where to start anymore I’m tired of hiding it I been wearing panties and leggings for a while and I want to move forward going out in my new clothes and shop some while I’m trying to get my grounds to make appointments on how and what I have to become a woman.

First, I’d like to address the last phrase you wrote: you aren’t becoming a woman, you’re already a woman! What you’re doing is figuring out how to share that fact with other people and the world at large. Don’t ever forget: you’re already a woman, and you always have been.

I’m not sure exactly what the first time I wore women’s clothes in public really is for me — there are so many ways to look at it!

  1. If I take the perspective that I’ve always been a woman, then any clothes that were mine were women’s clothes, so in that sense, I’ve always worn women’s clothes. But this perspective is probably the least interesting and not what you’re really looking for.
  2. If we aren’t talking about wearing them visibly, then I suppose there’s the time I snuck a pair of pantyhose on underneath my overalls when I was 5 or 6. But my brother did end up noticing them and pointing them out to the family, to my great sense of shame.
  3. Then there’s when I discovered that panties were way more comfortable than BWBs, and I switched over to wearing panties all the time – I was probably 19 or 20.

But what you’re probably most interested in is when did I start wearing clothes intended for women, while also knowing that I am trans/a woman? And again, there’s a few possibilities:

  1. The first time I remember visibly wearing women’s clothes outside of my home was to an appointment with my gender therapist. I took a denim skirt in the car with me and furtively changed into it while parked outside her office, then checked every direction for anyone who could potentially see me, and once the coast was clear, practically ran to her office! Nobody saw me (that I know of) until she came out to invite me from the waiting area into her office for my session. She noticed, and was very complimentary! Wearing skirts to my therapy sessions became a regular thing, and I even built up the courage to walk from the parking lot into a different office building, in full view of a busy McDonalds drive-thru. Nobody ever said or did anything that let me know that they noticed, and in hindsight, I doubt anyone who saw me from that drive-thru gave me a second glance.
  2. The first time I went into a public place in my skirt was at a PF Chang near my therapists office. I’d come from an appointment and my wife and I wanted to have lunch together, and I knew I didn’t want to take that skirt off and needed to break that ice somehow, so my wife went into the restaurant and got us a booth, and I came in a few minutes afterwards and went directly to the table and sat down. I was sure I’d been noticed, and we spent most of the meal glancing at the other patrons, feeling like they must be talking with each other about “the man who came in wearing a skirt!” Looking back now, I honestly don’t think most of the people in the restaurant noticed. Our server might have noticed, but she remained friendly and didn’t make any signals if she did.

Now, I remember those times with a bit of amusement over how wound up I got over the whole thing. Women’s clothes stopped being *women’s* a long time ago – they’re just clothes. No big deal.

Shopping! Now there was a stressful time! I did a lot of online shopping (Amazon is really good for that!), but you don’t get instant feedback and gratification from buying online. You’ve gotta go to an actual store for that!

The first time I recall shopping in the women’s section for myself was in an outlet store, where I found the aforementioned denim skirt that I ended up wearing for so many of those early public outings. I totally guessed at the sizing and thankfully got it close enough that it worked. My wife and family were also shopping for themselves, so I stealthily included my skirt with the clothes she had found for herself while I was holding her finds for her (as she continued to browse). I was nervous, but not nearly as much as shopping trips which came not long after.

The next major clothes shopping was at Kohl’s, where the goal was to find clothes for me. My wife was with me again, and once we got into the store, she asked me the very reasonable question “what would you like to look for?” In my state and with my utter lack of experience, my answer was “I don’t know! I don’t know where to begin!” I wanted to look at everything, but in my emotionally heightened state, I couldn’t last for very long before I was going to just break down from exhaustion. I think we looked at a few tops and maybe a skirt. I picked up a few shirts from the men’s section and sandwiched the skirts and tops between the men’s shirts and went across the store to the men’s section dressing room and tried them on, sure that a store employee was going to burst through the door and call the police on me! I think I got one skirt and maybe two tops that trip.

The next standout trio was again at Kohl’s a few weeks later. My wife and I met to shop for more clothes for me, and this time, I wore my denim skirt into the store!!! I discovered that because I was in the skirt, my anxiety was actually lower, because I was less worried about people potentially confronting me about browsing in the women’s section; after all, if someone wanted to ask me for whom was I shopping, a quick look at my skirt would answer that. I was able to feel more free to shop and pick things out, and in a short time, I had a pile of things to try on. Then, a catastrophe — my wife got called away and had to leave the store suddenly! I looked at the pile of clothes I wanted to try on and knew I didn’t have the heart to abandon my finds, and I knew there wasn’t any way I was going to sneak that pile into the men’s section fitting rooms, so I screwed up my courage and went to customer service and asked them if they had a policy on which fitting rooms I could use as a transgender woman. The (male) manager paused for a very brief moment, then responded that I was welcome to use the fitting room most comfortable and convenient for me, with the caveat that if I was in a room in the women’s section and another customer said something, I might need to exit those fitting rooms. So off I went, straight into the nearest fitting room, and tried on those clothes. I think I bought around 1/2 of them!

Since then, shopping has become way easier and more natural. My shopping style has become much more typical for many/most women, wandering around, touching the clothes and holding them up to my body in the aisles to get a sense of whether they might fit and look good on me. Shopping pre-transition was horrible – I felt like all those clothes were off-limits and that alarms would go off if I dared touch anything. Now, it’s thoroughly enjoyable!

As far as any comments or confrontations go, I’ve never had any negative comments from anyone in a store, but I’ve received a few compliments on the clothes I’ve found – from the cashier ringing up my purchases, to other customers!

So here’s the secret: most of the time, people simply don’t care who else is shopping for clothes near them. Store employees don’t care – they want you to buy things, and your money is as good as anyone else’s. Other customers don’t care, unless you’re blocking them from looking at something, and then it’s a quick “pardon me” and you let them by. The (cis het) men who are in the women’s section are either bored or intimidated by the women’s clothes, and most of the time they’re following their wives/girlfriends and holding the clothes for them, or, on their phones, trying to find a way to escape! And heck, I’ll bet more than a few of them are a little jealous of the women looking through these clothes!

So here’s what I’d recommend:

  • Have a shopping partner. Or a few of them. It’s really nice to have someone else to get their opinion of something you find, and if you’re feeling anxious, you get some plausible deniability having someone else there (“I’m looking at clothes for her.
  • The first time or first few times, have an idea of what you want to look for before you enter the store. This saves you from being overwhelmed once you’re in the store. If you want to find a skirt, then you can head to the skirt section and don’t have to deal with the sensory overload of tops and dresses. But if something catches your eye along the way, stop and check it out — that’s part of what makes it fun! Once you’ve done this a few times, it gets easier to just browse randomly.
  • Don’t worry about making fashion mistakes. You’re going to. We all do, and that’s ok. You’re essentially a teenage girl right now (especially if you’re just starting out on hormone therapy! 😂), and teen girls make mistakes and questionable choices all the time. The difference is they often get a free pass because of their youth, which we don’t get so much. But don’t let that stop you – make the mistakes, because that’s how you learn.
  • Pay attention to other women — preferably in real life, since media often sets unrealistic expectations of feminine presentation. Look at what they’re wearing and see what you like. I can’t tell you how many outfits have started with things like “I really like those booties that she’s wearing!” — then I go get a pair of booties and put together something similar.
  • Be patient with yourself; and forgive yourself. In clothing and in life. That’s just good advice for everyone!

And if, by chance, you come across someone who has a negative reaction to you, do your best to not let them get to you. Keep telling yourself “I’m a woman and I deserve to be here and wear these clothes, just like any other woman.” Say it out loud if you have the presence of mind – not for their benefit, but your own. Don’t let their negative words be the last thing your ears hear; replace those words with your own positive words, so that those positive ideas are what your brain is processing, not the negative ones.

You’ve got this. The hardest part is getting past the anxiety and fear, but I promise you, it is soooo worth it! Happy shopping!

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