Ashlee Simpson wishes she could delete a few outfits from her “Autobiography”.
“I’m definitely looking back and laughing at my fashion, because obviously I’ve always loved to mix and match – but it may have taken a second to fix it,” the “Pieces of Me” singer tells Page Six Style. to laugh.
Still, after years of experimenting with different looks, from punk rocker to pop princess, Simpson finally settled on the real thing (quoting his 2004 hit single) and his distinctive style: “70s boho.”
“It’s really something I always turn to. I’ve always loved high waisted, flared trousers, a tank top, and an eraser; it’s like my California weather,” she says.
This aesthetic is evident in Simpson’s new collaboration with Smash + Tess in a selection of tight-fitting slip dresses, gorgeous wide-leg jumpsuits and draped leggings, ranging from US$60 to $160 and available in sizes 3XS to 4X.
And the collection’s campaign shoot was a family affair, where Simpson modeled retro-influenced designs with her husband Evan Ross and 7-year-old daughter Jagger.
“If I’m doing something – even if I’m rehearsing – ‘Where’s my outfit?’ It was natural to let her in and have a mother-daughter moment,” the singer says, adding that Jagger “loves clothes.”
“I won’t be able to dress it up anymore. It’s all… It’s going to go in my closet and put on an entire outfit. I’m like, ‘Okay, I’ll save this for you,'” Simpson says.
But the star isn’t looking back at any of her past appearances with “LOVE.” Below, Simpson voices some of her most memorable red carpet moments over the years: the good, the bad, and “so bad, great,” as she says.
2003: Family Television Awards
“The scarf is cracking me up – it was something thing In that case. Why were we all wearing a scarf with everything?! … There’s a point where you really have to lose a piece, you know? A lot is happening.
“But at the same time, obviously, I’ve always loved a pair of pants. I still wear pants all the time.”
2004: Radio Music Awards
“I absolutely regret this… actually I don’t even know if I regret it because it’s so bad it’s great. Why was my signature boot a wrestling boot?!
“It belongs to that time, that period. It’s fun to look back and laugh. I wouldn’t be caught dead in this situation 1680619415”
2007: MTV VMAs (wearing BCBG Max Azria)
“Oh my God. I don’t know if I’ll be in a balloon dress [today]but I like this look – it was fun!
“Hair, makeup and clothes are all for playing and having fun. You should figure it out and try your luck. I certainly did this in the early 2000s; I To look like I’m trying to understand!”
2012: SAG Awards (wearing Jenny Packham)
“Again, I’m basically a tomboy, but this was a good moment for me. I loved that dress; It was elegant and definitely a step in a different direction. It was time to grow!
“I had also recently cut my hair; that hair was a fun moment.
2017: American Music Awards (wearing Christian Siriano)
“This was fun. It was an ode to Mama D [Diana Ross, Simpson’s mother-in-law, who received the Lifetime Achievement Award during the show].
“I love the shimmer and ombré of the dress; It felt like the right moment for that.”
2019: Grammy Awards (wearing Georges Chakra Couture)
“This jumpsuit was so much fun! I worked with [stylist] Maeve Reilly in this look; I loved the feathers.
“[Hairstylist] Ken Paves braided my hair through his ponytail, which suited the whole look. Always creative, coming up with great things – but at the end of the night it was impossible to go out!
2023: Vanity Fair Oscar Party (wearing Tony Ward Couture)
“This was a lot of fun for me because I don’t usually do bright colors. I was really happy that we went that way and went with red hair and dark lips. It was something different for me and I was happy with how it turned out.
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“The black lip balanced it out a bit in my opinion – so it wasn’t very sunny and still had an edge.
“I hadn’t dyed my hair in two years and didn’t feel like going the highlighted route. So I turned red … and then more and more red!