Ashlee Simpson Reviews All Her Past Hairstyles

Ashley Simpson
Photo: Getty Images (3)

" There's a mistake right there!” says a presently blond Ashlee Simpson-Ross, pointing to a photograph of herself wearing pigtail braids and a newsboy cap, from 2001. She's visiting the InStyle offices to tease new music that she and husband Evan Ross have been writing and recording, partly at her mother-in-law Diana Ross's Greenwich, Conn., residence. After pioneering famous-family reality TV in the early 2000s, with The Ashlee Simpson Show and her older sister's Newlyweds: Nick and Jessica, the 33-year-old is making a strategic return to the genre next month in Ashlee and Evan, premiering on Sept. 9, in the time slot directly following the Kardashians'. The show also serves as a genius delivery method for the couple's new album: each episode will culminate in the release of a new, soulful track.

So Simpson-Ross came to preview a couple of the under-wraps singles. And to talk about hair.

If hair tells the story of who we are, then Simpson-Ross's evolution is a plot-twisting page-turner. She's bleached her hair Debbie Harry-blonde, dyed it black to look like Karen O's, and taken inspiration from Karen Elson when going red. She's embraced the ombré, the pixie cut, choppy bangs, and peroxide mermaid waves. She's even picked up skills along the way; "my hairstylist, Jenny Cho, we would color each other's hair," Simpson-Ross says proudly. (She also works with stylists Ken Pavés and Christine Simmons and Riawna Capri of 901 Salon.)

"I had a real thing about changing my hair and trying every hair color. I've done everything," Simpson-Ross says, of her hairstyle history. "I think it was all a part of going through different phases in my life and trying things out." With each new look, she says, "I feel like you take a new personality on. That's the fun thing about hair — it's not permanent. You can go for it."

Now, her kids are carrying on the tradition. "Bronx, right now he has blue hair, so I guess he’s got a little mom in there," she says of her 9-year-old son with ex-husband Pete Wentz. Her 3-year-old daughter, Jagger, with Ross, prefers "Elsa braids," which Simpson-Ross is trying to master.

Growing up on screen turns the Internet into an easily accessible family photo album, which in some ways can be nice but also requires a sense of humor — so it's a good thing Simpson-Ross has one. We asked her to review every one of her hair stages, and she was more than game. Scroll down for Ashlee Simpson-Ross's very enjoyable 2001-2018 hair journey, narrated by Ashlee Simpson.

01 of 09

2001

2001
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"Oh my god, that is hysterical. I don't even know what's in my hair. Those must be clip-in extensions that are a really funny color. I look back at this era like, 'What was happening?' In general, this era is the worst era. These are the background-dancer days. I guess I was being ... I don't know. It's just all wrong. And the hat. It's, like, really bad."

02 of 09

2003

2003
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"That's definitely 7th Heaven Cecilia days," says Simpson of her stint on the show, her first major screen gig. "I had that fringe bang going on the whole time. I like a bang — but now, I just get bangs from breaking my hair. I kind of always liked a little edgy rock and roll, so I think at that time I was probably looking at a Debbie Harry, like, 'OK, I want this.' But now, I look at this hairstyle and I want to put my hands in there and mess it up!"

03 of 09

2004

2004
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"Oh, my God! This is hilarious. OK, so that was the first time I went for something different. I rebelled and bought a box of hair dye," says Simpson, explaining that she'd dyed her hair brown using an at-home kit, then gone to the salon to cover up her hack job with an even darker shade. "I had wanted to go black, and I can see here this is probably soon after I had dyed it myself because I feel like some of the browns are kind of popping through. Having dark hair with my roots, it would look like I was bald when my roots came in. But it was so me at that time. With that album [Autobiography], it was just where I was at, like 'Yeah! I'm feisty!'"

04 of 09

2005

2005
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"I remember this. This was right after I had done my L-O-V-E video. It was before people started doing that one, long piece [of hair]. That was a thing. I feel like there’s a Gwen Stefani moment going on. I liked her bleached hair. And there's the bang again! Hair, when you change it, it takes like a good two weeks to be like, 'Okay, I can be this person.' I think, as women, when we change it we obsess over it. But then two weeks later, I become one with my hair."

05 of 09

2006

2006
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"This is the worst ever! My makeup this day, I could die. What is happening here?! What is that, the heaviest contouring you've ever seen?" Simpson says. "I do remember that day. That’s one of the pictures that I go back and laugh at. I think I was on tour at that time. I liked that long hair to throw around. That is a ton of extensions! At that time I loved the long. It’s fun, especially when you’re doing shows."

06 of 09

2008

2008
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"I don't know what made me want to try red. Maybe Karen Elson. She looks really cool. I was like, 'I want to have a Karen Elson moment.' So I went red, and I ended up loving that. I was putting out Bittersweet World, and I don’t know that anything wild was happening, I just wanted a different moment. I really liked it, but I don't see myself dying my hair red again any time soon."

07 of 09

2010

2010
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"Now we’re short! It was so cute. I feel like the short hair was a couple years after I had Bronx. I just needed a change. I was going out of red hair, and I wanted to be bleached blonde, and in that process my hair was going to break. So I was like just, 'Let it break, and I’ll have a short hairdo and do the pixie!'" Was she scared? "A little bit. I remember the shock of cutting all of my hair off and having a pixie haircut at first. I was like, 'Ahh, I look like a little boy!' But it was really fun.Whenever I did my hair short I felt like I needed to dress a little girlier.I wore a lot of cool, big earrings."

08 of 09

2011

2011
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"I liked that color! That was chocolate brown with ombré. I’ve always like ombrés, with blonde, with dark, whatever. And I used to take my hair, and I’d be like, ‘Guys, let’s grab the bleach and let’s place it here, here!’ I really got in there."

09 of 09

2018

2018 Billboard Music Awards
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"Here we are! My look now just feels like me. I’m just in my me moment. I feel like it’s not too long, it’s not too short. It’s just being me. Most of all, my hair is easy. I get it colored, like, every 4 months. [I keep it down], or when I work out I wear a bun because I sweat a lot. What else do I like? I like a French twist.Ithink this is the longest I've stuck around the same hair moment."

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