What were the most embarrassing fashion mistakes of your youth?

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If anybody tries to tell me that they never made a fashion mistake, I will come to the conclusion that they are either lying, fooling themselves or have spent their entire life being totally 'safe' in beige and navy. I'm sure I'm still messing up on a regular basis - certainly my Italian and Portuguese colleagues always look at me like I'm in need of a style make-over - but like most people, my worst crimes against fashion were in my late teens and 20s. My mother frequently used to ask me "Are you REALLY going out like that?" but I don't recall that she ever sent me back to my room to change. I had no money in my student days but I had a lot of access to jumble sales (I think the US calls them 'rummage' sales), charity shops filled with dead men's and women's clothes, and lots of vintage stores. I was also more than capable of hitting the home-dye kits and abusing my mother's sewing machine. Probably my lowest low point was tie-dying old men's 'long johns'. I like to think I pre-dated the trend for 'leggings' but strangers would comment on my wrinkly baggy knees and my saggy crotch (it was the long johns that were saggy, not my actual crotch - all was much perter then) because I also pre-dated lycra. My German army surplus home customised trousers were pretty terrible and smelled like an old wet dog. My mother hated them. And I had far too many disgusting old men's tweed jackets and saggy old lady cardigans. My mother's old school gym skirt got quite a lot of outings too and I used to pair it with a very loud black and red 'Dennis the Menace' top. Once I started work, I had a shocking collection of terrible skirt suits. It's a wonder that all the polyester rubbing together didn't cause me to spontaneously combust. Come on now, please don't pretend that you've not done the same. Please tell me some of your worst fashion excesses and disasters.