How I Shop: Ashlee Simpson Ross

We all buy clothes, but no two people shop the same. It can be a social experience, and a deeply personal one; at times, it can be impulsive and entertaining, at others, purpose-driven, a chore. Where do you shop? When do you shop? How do you decide what you need, how much to spend and what's "you"? These are some of the questions we're putting to prominent figures in our column "How I Shop."

In the early-to-mid-2000s, when millennials like myself were in high school, we were hard-pressed to find a better source of back-to-school style inspo than Ashlee Simpson. Her alternative-meets-boho aesthetic felt both original and approachable, her go-to Vans, belted low-rise pants and piles of jewelry making for an easy teen outfit recipe.

Twenty years later, she's building on this legacy via a back-to-school campaign for shoe retailer DSW, in which she stars alongside her husband, Evan Ross, and three children, Bronx, Jagger and Ziggy — who are now (literally) following in her sartorial footsteps.

I caught up with Simpson Ross while she hosted event in Los Angeles to celebrate the campaign launch. Read on for her reflections on her 20-year-old "Autobiography" style era, the items she still keeps in rotation today, her biggest fashion icons (one of whom she's related to) and the 2000s trend her daughter's embracing today.

"I had a lot of fun with my style back then, for sure. I always wanted to do something, as an artist, that felt comfortable. I feel like now everybody's wearing guy's shorts, but I always wore big, baggy shorts... and lots of accessories, which was definitely a thing back then. I always wanted to feel like myself. I feel like I would put some wild numbers together sometimes, but it was really whatever I was feeling. Looking back on the clothes that I wore — I mean, I love it. It's such a moment in time. It's fun to reflect on that.

"Some of them I'm like, 'Wow, wrestling boots and a tutu? You know what? I felt chic that day. That's all that matters.' So, looking back on it, I love that moment. And it's fun to see some of those trends coming back. It's even funny with my daughter — she was watching some of my videos from back in the day, and I saw her do the double-belt situation. I was like, 'We got to get you some Dickies and a double belt. I got to go to my storage and gather all my belts.'

"I definitely have things and pieces from each era and time that I've kept, which is fun. It's always funny to see what comes back. Everything recirculates. I love that about fashion because, for me, even to this day, I do love an '80s or a '70s, and now we've become that.

"My [first splurge] was... I remember the day I went to Chrome Hearts and got a ring. That was exciting. I still have that ring. I still love Chrome Hearts.

"I'm still a creature of comfort. I love a men's trouser. I clearly love menswear. I love having staples like a good blazer or even my husband's blazers. That's one thing that I've always stuck to. But I think that, if it's a carpet or something, I'm a bit more elegant now. In my day-to-day life, I'm definitely chasing kids, so I'm a sneakers kind of girl, with a baggy jean or a trouser. Right now, I'm into the longer short — it's so hot outside. I love a ballet flat, and I always have. I call them my Amy Winehouse shoes.

"When I performed back in the day, I always wore Dickies. I think it's finding a pant that you feel like you can jump and move around in. You find pieces that will bring a little bit of the fun or pop. When I'm doing a show, I still want to rock out and jump around and dance — so, something with movement.

"I love looking at Stevie Nicks or Debbie Harry. Those moments are always amazing. But my mother-in-law [Diana Ross], she's a style icon. She's the queen. When I'm looking for a cute, summery outfit, I also love Jane Birkin.

"I'm an in-person [shopper]. I'm not good at online. I feel like everything fits so differently. I love in-person and to see it, because I feel like when I do online, I always purchase the wrong things, and then it's more stressful to return it all. I love vintage. I love finding something that feels like it stands out.

"I was just in Europe, and Dover Street Market is my favorite. They have so many cool, eclectic pieces. I feel like a good go-to for my trouser situation that's not overpriced is Frankie Shop... I just got a cute Comme des Garçons suit.

"I'm definitely a fan of sneakers. I have a big collection. It's a lot of sneakers and a lot of flats. I do have my heels... Usually it's a Saint Laurent or something like that. But my sneakers, I wear Adidas all the time. I love a Converse. What am I wearing right now? These are Reeboks. I love that old-school style. With my kids, too, I'm always putting them in Adidas and New Balance.

"That's what I love about DSW — it has such a variety, and I feel like everyone can really be themselves there and find what shoe they want, which my kids really do like to pick out. Jagger is definitely drawn to the pink and the bright colors, and, for Ziggy, it's having that comfortable Croc and having shoes that are easy for school and play. Bronx, I mean, he picks out what he wants. My kids wear a uniform at school, so that's really the place where they can express themselves, with their shoes."

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