Should I cut my hair short?

About once a decade I lop all my hair off. It’s a look that has always worked for me, but now at sixty-three years old I think it might not look good on me anymore. I don’t have a picture, but here’s a screenshot from a video of me the last time I cut it short. It’s been a while come to think of it. Scroll down, please.

I found this picture of Madonna with a cut that might work. I can’t decide if I can pull it off!

Stacy Horn

I've written six non-fiction books, the most recent is Damnation Island: Poor, Sick, Mad, and Criminal in 19th-Century New York.

View all posts by Stacy Horn →

3 thoughts on “Should I cut my hair short?

  1. Yes, do it! Short hair is uplifting and that’s a cute style in the picture from the video. Madonna picture not so much. But these decisions are hard to make for some reason.

  2. I say YES! But then again I normally have and love very short hair. It’s in a bob right now, mainly just for a change, but I think I’ve only got a month or so left before I have to cut it off again. I feel like I’m in a “Boring Middle Aged Lady” costume. I AM a boring middle aged lady, but a nice short cut makes me feel marginally more sassy.

    If you do it and it’s not for you anymore, it’ll grow back, no worries. And I agree that the top picture of you is a great style.

  3. I’m all for short hair, but it’s really hard to find someone who knows how to cut short hair for 60-year olds without it looking like a helmet.

    I had a great stylist for three years but she moved back to PR permanently after Hurricane Maria to help out her family and now I’m getting one lousy cut after another, from California to Long Island. I like it short in back and long in front, but no hairdresser believes me — they always leave too much in back and it looks like a 1950s page boy.

    I take a photo of Meryl Streep’s hair when she was in The Devil Wears Prada to show what I want. And now, I make sure that the haircutter LOOKS at it, and I tell her what it is I want from that photo. Because once, after the stylist glanced at it and started cutting, she asked me when I’d had that picture of me taken.

    So many stylists see a lady with gray hair and think…”Grandma”. So, if you find a good hairdresser who knows how to cut cool hair, please let me know?

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