Your Afternoon Chat: What Are Your Biggest Fashion Regrets?

Fashion

All the current flashback posts have been making us all, I think, dive back into our mental photo albums and recall the things we wore, the stuff we coveted, and the things we’d like to pretend we never did. For example, I definitely bought stirrup pants in 1990 or 1991 — from Express, I’m 99 percent sure — and honestly, I even knew they didn’t look good on me but I wanted to feel like I had An Outfit, so I got the tunics and the stretchy pants and then probably wore them once and then recoiled from them.

I’ve definitely bought a couple small things here and there that make me laugh now — the corset going-out top, the super-low-rise Lucky Brand jeans — but I don’t know if I have any real regrets that aren’t pegged to, “Well, it was great at the time,” except of course for those stirrup pants (I KNEW BETTER, WHAT WAS I DOING). I did do a dumb thing to my hair. I hated wearing my hair in a ponytail because I was self-conscious about my face, so one day I cut just a liiiiittle bit next to my face so that there would be some tendrils, and my mom was like, “WHAAAAAT?” She took me to get it fixed properly, and the hairdresser cut actual thick side bangs which looked TERRIBLE. I have a cowlick in front and a side part and he a) didn’t take that into account, and b) wanted me to blow-dry them straight up and then let them fall to the side for height? I couldn’t, and also, they looked like a fountain that way. We moved to Miami right after I did that, and so for two years in school there in a city I just sincerely loathed and where I never felt like I fit in, I also had a dumb bang situation. I kept trying to grow them out, but then I’d get impatient because they’d start to flip up at the bottom if they got too long and it embarrassed me so I’d trim them again. So while I avoided the ’80s perm, I did at least have about two and a half or three formative years with embarrassing hair that was more or less my fault. And let’s not even get into the people who tried to layer my hair once it turned curly and did not know what they were doing. Clump city.

I wish I had a more dramatic regret. Here’s a story about planning gone wrong: When I was six– about to turn seven — I had saved a summery pink and white striped skirt and t-shirt for a special occasion (and also warm weather), and we finally had one when my parents hosted a party for my school. A lot of the teachers were there and I was very proud to show off our house and my cool cool pink and white outfit. At one point I went to the restroom and came back, and wandered around, and apparently for a good while my skirt had been tucked into my underwear. Is it weird that I still remember that and shudder? So, while I did not regret my outfit, I apparently do not always execute the slam-dunks.

What about you? Anything you regret, or anything you thought was a surefire hit that backfired on you completely?

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