Puttning my mothers clothes back in her closet without ger noticing it... Long time ago.

Also later on buying clothes and shoes. I was very shy as a kid. I remember one time I was shopping for a pair of high heels in my teen years. Traveled to The other end of my town. Got into the mall looking for stores.
Got into a shoestore quickly scanning for the most feminin shoes. Found them. Then got in line at the cashiers, heart pounding, money in my hand.
The cashiers, a girl maybe around 20 years old grabbed my shoes and said "well honey thoose are very high heels can you manage them?"
I just mumbled something and handed over the cash. Got the merch and hurried out... How could she know was in my head, my head was spinning. Lucky me there was nobody I knew lurking around. And I did manage thoose high heels.

Everytime buying female stuff got me high. It was scary but so exciting. Like a rollercoster. Sometimes dissapointment getting home and nothing fit.
I have bought tons of clothes not fitting. Still happens but nowdays I'll send it back.

I was not so advanced that makeup was my a-game but later on internet and Youtube fixed that.