Quick Question: What Was Your Most Regrettable Hairstyle?

Anyone over 30 who lived in New Jersey in the early '90s, I already know your answer.
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Publish date:
June 10, 2013
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short hair, Quick Question, long hair, haircuts, hairstyles

When I was a little girl, long hair was my thing.

I distinctly remember feeling like it was part of my identity. There was an unspoken competition in my mind between myself and Michelle, the other really-long-haired girl in my elementary school's gifted program. I felt really proud when, on Halloween, strangers thought my hair was a wig.

When I had my first major haircut in fifth grade, ABOVE THE SHOULDERS, I remember the BFF smiling behind me in the photo above, Betsy, being genuinely upset.

From that point on, sometimes I had long hair, sometimes I had chin-length hair, sometimes I had short hair. Long hair was no longer my signature, so I felt free to try any ol' haircut I damn well pleased.

But then, as a relationship was ending a few months after 9/11, I went REALLY short. Alyssa-Milano-on-the-sixth-season-of-Charmed short, except before that even happened.

Katie has already made a riveting argument for not having to be skinny to pull off short hair, and I think the fact that I'm 40 pounds lighter in that photo than I currently am only furthers that argument. I have a long face, and being thinner at the time only elongated it in a weird way. I NEEDED some framing around my face so as not to look so much like "The Scream" by Edvard Munch. Or Detective Munch from Law & Order SVU.

Whenever I get tempted to go suuuuuper-short (which, during the summer, is every 15 minutes), I just look at that picture and remind myself that it's probably not my best look.

How about you? Quick Question: What was your most regrettable hairstyle? Bonus points for photos!