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Fashion Guffaws and Woe-Some Trends

Even the Most Style-Savvy Among Us Made Mistakes

"In college, I inadvertently tucked my skirt into the back of my bright red granny panties, walked through the whole student lounge and only noticed when I finally sat down on a surprisingly very cold chair. Moral of the story: pick your underwear wisely.” - Stephanie Szostak, Actress

"A perm @1986. I have naturally huge hair. So, why??" - Alisyn Camerota, CNN Anchor

"When I was 17 and going to my senior prom I wanted to wear a long sleeve acid green wide leg lace jumpsuit that was totally sheer except for the body. My mom thought it was hideous and said if I wanted it I would have to pay for it myself. I got a job, bought it, and wore it… of course no one wore anything remotely like it. It WAS hideous in retrospect, but I was still voted “Most Sophisticated” in my Class of ‘69!" - Sunny Sherman, aka @OldFashionGuru

"I have always felt that fashion should be a fun expression of oneself, but there are times I look back at photos and wonder what I was trying to convey at that time! There were many days of big hair, fishnet stockings and high heels!! I’m sticking with ‘It was the ‘80’s!" - Kitt Shapiro, Owner of West

“What a difference four decades and walking away from a perm makes.” - Stephen Kempson, Owner of Stephen Kempson London

"The top knot headband trend that is still going strong and while I don't hate it, I definitely regret committing so hard! Looking back its the 'headband era' where normally I just sprinkle a trend in a little bit... I was wearing a different headband every day of the week!" - Zac Mathias, Founder The Classic Chic

  • Stephanie Szostak (Photo: Jerri Graham)
  • Alisyn Camerota (Photo: Mike Cohen)
  • Sunny Sherman (Photo: Guy J. Sherman)
  • Zac Mathias (Photo: Julia Dags)
  • Kitt Shapiro
  • Stephen Kempson without a perm!
  • Stephen Kempson then and now...