Not so much a wardrobe issue but the August right before I started the 7th grade, my mother and an aunt talked me into getting the very short pixie like haircut that was very popular in the early 90's...amongst middle aged women. I cannot remember a single girl in my school who had that hairstyle.
They convinced me by saying "Oh it'll be so nice and cool and easy to take care of!" Well that was a colossal LIE because the way my hair was cut, the hairdo looked awful if all I did was wash it and let it airdry. No, I had to use a round brush and hair dryer every morning to get it to look even half decent. And I hated high maintenance haircuts then and do now. Not that I don't care how my hair looks, cause I do but really, most often my daily style is a ponytail. A bun if I feel like getting fancy.
The extra fun bonus was that it gave the other kids more reason to bully me. "Hey pirate, are you gay?" No you morons, I changed my hair length, not my sexual preference. "Hey pirate, who's your girlfriend?" I came home after a week and announced I wanted to grow it out. Nope, give it a month I was told.
Well a month later one of my aunts calls to announce she's getting married and would I be a bridesmaid?" Excited I said yes and was told my my mother I had to keep my hair as it was because she didn't want it in the awkward growing out stage when the date of the wedding came around, which was in April and this was in October. I still am convinced she knew that her baby sister was going to do that and that's why she put me off in letting me grow it out.
I have heard so many people tell me "Oh but you looked so cute with that hairstyle!" GAH!! My bff, bless her said "It is a cute hairstyle but it's not really you so I can see why you didn't like it."