What was your biggest fashion fail?

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I thought I looked trendy

One of my biggest fashion fails happened when I was a high school English teacher. I had a skirt that cut off at my knees that I thought looked really cute with a pair of black leather boots. I thought I looked trendy and everything was covered up just fine, but when I walked into class one of my students was all, “Ohhhhh Ms. Bouska, looking naughty today!” and I was utterly creeped out, embarrassed, disgusted — all of the above. I never wore that combo again.

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