Mine was a light green nightgown that had flowers sewn all over the top.

A maroon leotard and a wrap skirt.

Shoes from Goodwill.

skinny jeans (eh)

Panties came first sometime around age 15 or 16. My first outer wear were women's jeans and a t-shirt, decades later, jeans are still one of my favorite things to shop for.

When I was 12 the family and I went into lifeline for a browse and I found this women's size 12 jacket which I fell in love with and my biomum bought it for me. As for me buying something,  I bought a pair of women's jean-shorts when I was 17ish. I had got a lot of other things before then but I didn't actually 'buy' them.

DanielleA Are you saying what I think you're saying? *ahem" five finger discount *ahem*

A black bodycon top with a large v-neck followed by a long pencil skirt.

The first item I'm sure of was the bloomers my mother bought for me as swimwear when I was in elementary school. I think her only criterion for the choice was size. I very much liked them and used them for many years. I only realized they were intended for girls after I outgrew them and started searching in earnest for something similar to replace them.

The first item I remember buying for myself was a dark blue short-sleeved shirt at my junior high school thrift shop. I got it because I loved the cut. I was again unaware that it was meant for girls until it eventually registered that that must be why the buttons were on the left side.

Quote from: blossom on March 27, 2016, 06:29:07 PM
DanielleA Are you saying what I think you're saying? *ahem" five finger discount *ahem*

Kind of... Mostly I was given girls clothes from friends I had made while going on "walk about" as a kid. But yeah I had learnt as a child to steal food to survive while the slack biomother smoked our Centrelink money away. And then I learnt that I could get the clothes I wanted too. Just silly/risky things I did as a kid.

Satin panties, 5 pairs, that was the first items I ever bought for myself.  Then a bra and skirt.

Josefa

Quote from: pj on March 24, 2016, 11:28:37 AM
Shoes from Goodwill.

ditto...hey what girl doesn't like shoes

I bought a simple black dress from the local lgbt shelter's thrift store. It was the perfect first shopping experience,

High heel shoes with the three bands resembling Adidas and faux laces. That was more than 10 years ago, long before I realised I was trans.

I feel so boring but mine were several pairs of black tights!

A bra and ofc I bought the wrong size.

A grey cropped jumper from the Alexander Wang X H&M Collection, and a black bodycon bardot dress from ASOS

Panties, long before I knew I was trans.  I just thought I was kinky.  The first outerwear I bought was a skirt.

I first bought women's clothing when I was in my early twenties. I went shopping and bought an outfit.
Heels, hose, a corset and a bra, with a little black dress. While on that same shopping trip, I stopped at this place in the mall and got my ears pierced. When I got home and put it all on, I couldn't stop staring at myself in the mirror. It felt so right and I was so happy with the way I looked.

A pair of boots for a costume party. They were knee high with a 2-3" platform and a 6" heel. Surprisingly extremely easy to walk in- and everything else was my (then current, now ex) girlfriend's, which I ended up keeping.