My Hairstyle Icons: An (Embarrassing) History

The 70s had Farrah Fawcett. The 80s had Pat Benatar. What will be my generation’s legacy?

I took a look at the hairstyle icons I’ve emulated over my life, and the results were at least a little embarrassing…

my very first hair icon

my very first hair icon

“Not even three years old, she knew that yellow hair is king.”
-Tina Fey

1. The Rachel

Was there anyone that didn’t have this haircut? I was in elementary school when Friends debuted (And, btw, in college when it ended. No wonder it was my primary model for adulthood.) After 11 years of not caring about hair, I suddenly needed the Rachel.

side note: Courteney Cox had basically the same haircut. why did Jen get all the glory? credit

Cox had basically the same ‘do. Why did Jen get all the glory?

And, not to be one of those ladies from What Not To Wear that gets stuck with the same hairstyle for 30 years, but I still require some variation of layers and angles to this day. So, in a way, the Rachel never really left us.

To be fair, my friend Caitlin had this haircut first, but we thought it was weird and made fun of her nonstop until Jennifer Aniston arrived on the scene.

Jumping way ahead, because high school was a bad time for hair (for me)…
2. The Ashlee Simpson

AKA the Pieces of Me. Remember that awful song? My roommate Brianna secretly listened to the album in her car, which made it all the more amusing when she got caught, because she’d tried to hide it.

I don’t know who made us all go blonde in the first place. Why not blame Jessica Simpson? But then Ashlee dumped her 7th Heaven blonde look, decided she would pretend she could sing, and sheep (like me) everywhere threw their peroxide out the window.

photos: credit / credit

photos: credit / credit

Society was all “You have blonde hair? Still?? Fix that shit and get a nose job while you’re at it.”

...and then go red.

…and then go red.

For the record, I liked her old nose better but she didn’t consult me. She’s probably happy with the outcome though so, good for her.

3. The Freaky Friday

lindsay lohan freaky friday

Maybe I’m alone in my millennial admiration for Lindsay Lohan, but a few people told me I looked like her (freckles are our only common feature), I took it as a compliment, and ran with it.

couldn't really find a good pic but you get the gist

couldn’t really find a good pic but you get the gist

When I get a personal stylist on staff, I’m going back to this look.

4. The Portia

AKA the Honeymoon. Portia de Rossi has great hair. I do not. But this was one style I was able to copy. Technically, I didn’t copy it but just happened to get a similar cut around the same time.


Portia and Ellen in Italy

Jill and Tom in Italy

Jill and Tom in Italy

…We’re practically twins. Except that Tom and I had to be our own paparazzi.

I have to admit, this haircut was an impulse. It turned out cute though, for a while. Now I’m still waiting for my lopsided hair to even out.

Now, the question you’re all dying to know the answer to: who will my next hair icon be?

Accepting applications below.


  1. All I’m hearing is you went to Italy. And now I hate you.

    P.S. I vote for The Emma Stone.
    Stephanie recently posted…A Different Kind of HeroMy Profile

  2. Man, it’s so much easier for us dudes. We usually find one haircut we like and go to the same barber for years on end.
    Phil recently posted…When ya just gotta do the #2 in NYC!My Profile

  3. I hate to admit it… I’ve had the Rachel cut… the Rachel bob… and the Rachel layers. I did do the the Ashlee Simpson at one point with the side bangs, except my bangs ended up looking too blunt and my friends decided it would be cool to call me Dora the Explorer the rest of the summer.
    an example of my Dora bangs!

    Love your blog Jill!!! :D

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