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When did you first purchase your first women’s wardrobe or piece?

Started by Robyn Zola, August 18, 2026, 01:11:49 PM

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Robyn Zola

Hi, everyone, this is a question driving me crazy because I've finally given myself permission to like all the women's styles that I had loved all my male life but couldn't wear.

But... I'm afraid to buy anything yet. I have no idea how much HRT will changes my sizes.

I've always known the women's styles that I love and only now found out the names for them (dark academia, edgy, and boho - as one style guide suggested picking the top three favs and develop a personal style from that).

So, I want to go thrifting and build a capsule wardrobe piece by piece. I want to do it smartly, starting with essentials that can mix and match with each other – no dopamine buys! Only strategic shopping to keep clutter down.

But again, what will the HRT do? I found a wonderful woman's mid-thigh length tarten kilt, hand made in Scotland (but how do I know what my hips and waist will be?). Oh, some wonderful cognac leather knee-highs perfect for Autumn (will HRT shrink the ligaments in my feet to a smaller size?). I saw an extraordinary woman's tweed blazer in the thrift store (how big are my tits likely to be?).

I suppose I could start with a nice cashmere black turtle neck. I saw some lama-wool winter tights on etsy. Maybe a winter coat? Does a jacket also depend on breast size for fit?

But wardrobe basics? When did everyone else start?
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Maid Marion


Devlyn

Nobody knows how your body is going to change on HRT, it's strictly a YMMV situation. I wouldn't buy anything expensive that fits now, because it probably won't fit later.

Hugs, Devlyn

Robyn Zola

Hi Marion - yes, I like the idea of the little black dress.

Devlyn, yes, I'm actually trying to avoid anything expensive in any case. My mom is a retired art professor and she ALWAYS bought her clothes in thrift stores. Of course, 1) she always had a talent for finding the good stuff, and 2) it was Atlanta, where rich ladies would wear expensive lines once or twice then send it to the thrift store - that's how she had an amazing wardrobe. I hope to do something similar.

But yea, I'm afraid of getting something nice then not being able to wear it. I mean, at my age I don't expect to start noticing anything until six months in or so. But even then, one could have aq drastic change later. So, I was just curious how others managed it, especially with RLE - which the German insurance companies still expect.
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Lori Dee

Also remember that HRT changes fat distribution, not bone structure. So feet, hands, arms, and leg length are not likely to change.

The fat redistribution is also very slow. I wore stretchy jeans for almost three years before I finally reached their limit. But by then, I was ready for new ones - something different anyway.

@ChrissyRyan has a good philosophy: Every time you buy a new piece, donate the old one. That goes for tops, bottoms, bras, whatever. Lots of ladies out there (like you) are looking for something that fits their budget.
My Life is Based on a True Story <-- The Story of Lori
The Story of Lori, Chapter 2
Veteran U.S. Army - SSG (Staff Sergeant) - M60A3 Tank Master Gunner
2017 - GD Diagnosis / 2019- 2nd Diagnosis / 2020 - HRT / 2022 - FFS & Legal Name Change
/ 2024 - Voice Training / 2025 - Passport & IDs complete - Started Electrolysis!

An ancient prayer:
"King Zeus, grant us the good things, whether we pray for them or not, and keep from us the bad things, even if we pray for them."

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Robyn Zola

Thank Lori ... so I'm probably safe buying picking up wonderful boots! Winter long coat, sweaters, should be ok too. Stretchy jeans is a great idea! Oh, with donating, the Queer Centre in Erfurt has a program when I can donate my good 'man' clothes for FtM individuals. So it is a good idea to follow ChrissyRyan's suggestion and keeps the wardrobe [the furniture piece, we don't have closets] less cluttered.
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Lori Dee

Quote from: Robyn Zola on August 18, 2026, 02:13:41 PMOh, with donating, the Queer Centre in Erfurt has a program when I can donate my good 'man' clothes for FtM individuals. So it is a good idea to follow ChrissyRyan's suggestion

Yes, donating to an LGBTQ Center is a great idea. I have also donated clothes to women's shelters. There is always someone in need.
My Life is Based on a True Story <-- The Story of Lori
The Story of Lori, Chapter 2
Veteran U.S. Army - SSG (Staff Sergeant) - M60A3 Tank Master Gunner
2017 - GD Diagnosis / 2019- 2nd Diagnosis / 2020 - HRT / 2022 - FFS & Legal Name Change
/ 2024 - Voice Training / 2025 - Passport & IDs complete - Started Electrolysis!

An ancient prayer:
"King Zeus, grant us the good things, whether we pray for them or not, and keep from us the bad things, even if we pray for them."

HELP US HELP YOU!
Please consider becoming a Subscriber.
Donations accepted at: https://www.paypal.com/paypalme/SusanElizabethLarson 🔗
  • skype:.?call
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Charlotte Kitty

I've been buying women's clothes and was wearing them boymode for years before transition. I'm 18 months HRT and apart from bras, I still fit in everything I bought at the start of transition. Still fit all the women's stuff i bought in boymode too.


Laura Squirrel

I remember buying a purse in late summer or early autumn of 1998. I can't find a pic at the moment. But it looked just like the purse that Marisa Tomei wore in "My Cousin Vinny". A shoe store in my neighborhood was closing down, and I got it for cheap. I was soooooo nervous. These days, I would obviously approach things in a more confident manner. But since I was still living as that dumb impostor, I was really weird about it. I'm glad that time is gone. But, having said that, I still hate this current period in time.


Stottie Girl

I've been buying female clothing since my early teens. I ordered some school uniform like clothing when I was still in school so I could look like the other girls, I've worn teeny fashion, club wear etc etc right up to now. I certainly wouldn't advise teeny fashion or skimpy clubwear for someone your age!

I think wardrobe essentials depend massively on what your style will evolve into. As Marion says everyone should own a little black dress in my view but for a whole wardrobe you want leggings, maxi skirts, skinny jeans, a variety of tops, skirts. Jewelry, makeup, perfume, likely a wig unless you have grown your hair out. ankle boots are very versatile and easier to learn to walk in than strappy sandals. Thrifting is an excellent way to build your first wardobe. I have a lot of good clothes doing that.Look out for clothing bundles that people are selling. They are sometimes hit and miss but it helps you get an idea what suits you and what sizes to go for.

Size wise you won't really know. You will be whatever your genetics will allow. There is no way to know really. I would not worry about it just yet though as body shape changes take years on HRT (though breast growth can be quick initially) experiment with styles now and as your body changes your style will too. I would strongly recommend keeping a log of your main measurements bust, underbust, natural waist, high hip and hip. This will show how you are changing on HRT and is a very useful reference guide to your transition. I have a log going back to 2015 though i was stop starting HRT back then with big gaps in between.
A wise man once said don't judge a man until you've walked a mile in his shoes, that way when you judge him you're a mile away and you have his shoes!

Never trust a man who, when left alone in a room with a tea cozy, doesn't try it on - Billy Connolley

Laura Squirrel

Quote from: Stottie Girl on August 18, 2026, 05:52:23 PMI've been buying female clothing since my early teens.

How did you manage to pull that off? Where did you hide it?
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Stottie Girl

Quote from: Laura Squirrel on August 18, 2026, 10:34:30 PMHow did you manage to pull that off? Where did you hide it?
Under my bed mostly! It was not very successful! I had my stash discovered several times leading to blazing rows with my dad and making promises I knew I wouldn't be able to keep! The final time caused me to move out of home. I only dressed late at night when they were asleep or when they went out or on holiday.
A wise man once said don't judge a man until you've walked a mile in his shoes, that way when you judge him you're a mile away and you have his shoes!

Never trust a man who, when left alone in a room with a tea cozy, doesn't try it on - Billy Connolley

Laura Squirrel

Quote from: Stottie Girl on Yesterday at 01:38:12 AMUnder my bed mostly! It was not very successful! I had my stash discovered several times leading to blazing rows with my dad and making promises I knew I wouldn't be able to keep! The final time caused me to move out of home. I only dressed late at night when they were asleep or when they went out or on holiday.

Okay. LOL So, we did the same thing. I was constantly busted. When I would crossdress, it was for around an hour or so once I was home from school.
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Finally Anna

I am honorable chairperson in the the club "bought stuff when young and living with the parents, and got busted". I would guess that there's quite a few members from that club, here at Susan's.
All the world's a stage, and all the men and women merely players.
To thine own self be true.

Out to self since March 5, 2026. My wife knows it all since June 23.
Integration ongoing. I'll cross the transition bridge when I get to it.

Stottie Girl

Quote from: Laura Squirrel on Yesterday at 09:45:36 AMOkay. LOL So, we did the same thing. I was constantly busted. When I would crossdress, it was for around an hour or so once I was home from school.
Ha ha! Yep same for me! I usually had a two hour window after school if I was lucky!
A wise man once said don't judge a man until you've walked a mile in his shoes, that way when you judge him you're a mile away and you have his shoes!

Never trust a man who, when left alone in a room with a tea cozy, doesn't try it on - Billy Connolley
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Laura Squirrel

Quote from: Stottie Girl on Yesterday at 12:49:30 PMHa ha! Yep same for me! I usually had a two hour window after school if I was lucky!

Mine was 4 pm until 5. That was when my father would get off work.
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Charlotte Kitty

I must say I did have certain items of womens clothing that I hid when I was still living with parents. Nothing ever got found. I'm thankful as there were things that would have made finding just womens stuff tame in comparison!
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Robyn Zola

Thanks everyone for the inspiration. I went thrifting today. I found a very nice pair of grey flannels for a sort of Marlene Dietrich look. A black merino half- turtle neck and another black full turtle neck and a neat black blouse. I wanted to go for the houndstooth mid-thigh skirt, but I just don't know how I will turn out with regards to HRT.

But thanks everyone, you inspired me and it was euphoria trying everything on even when they knew I was male. I loved it!
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Stottie Girl

Quote from: Robyn Zola on Yesterday at 02:38:50 PMThanks everyone for the inspiration. I went thrifting today. I found a very nice pair of grey flannels for a sort of Marlene Dietrich look. A black merino half- turtle neck and another black full turtle neck and a neat black blouse. I wanted to go for the houndstooth mid-thigh skirt, but I just don't know how I will turn out with regards to HRT.

But thanks everyone, you inspired me and it was euphoria trying everything on even when they knew I was male. I loved it!
You should have just bought the skirt Robyn. Buy for the present not the future. If it turns out not to be right you can be the one selling them to get more stuff. Let's be honest, once you get the bug, shopping for female clothes never gets old!
A wise man once said don't judge a man until you've walked a mile in his shoes, that way when you judge him you're a mile away and you have his shoes!

Never trust a man who, when left alone in a room with a tea cozy, doesn't try it on - Billy Connolley