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How I Shop: Lexi Underwood

The "If Not Now, When?" and "Little Fires Everywhere" actor (and new Disney Princess!) shares what she loves about '90s flared yoga pants and how Aaliyah and Rihanna continue to inspire her.
Lexi Underwood at a Hulu event in February 2020.

Lexi Underwood at a Hulu event in February 2020.

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 last year's "Little Fires Everywhere," Lexi Underwood held her own and stole many a scene from seasoned co-stars Reese Witherspoon and Kerry Washington. While keeping audiences entertained (and comforted) in the early stages of lockdown 2020, the now-17-year-old also realized one of her own teenage fantasies in the 1997-set Hulu series, based on Celeste Ng's bestseller. 

"I draw a lot of inspiration from the '90s, so one of my favorite parts about being on the show was actually the wardrobe," says Underwood over Zoom. "My very first fitting, I came in and told Lyn Paolo, our costume designer, 'I feel like I'm living out my dreams of being a '90s teenager! Everything that I see on the Internet and YouTube, when I look up old clips of the '90s, it's right here. I feel like I fully transformed into like a '90s teen."

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But in her latest project, "If Not Now, When?" (premiering on demand and digital on Friday, Jan. 8), Underwood plays a current-day high schooler. She continues to make me cry as her character navigates a close but complicated relationship with her on-screen mother — this time played by Meagan Good, who also co-directed the movie with writer and co-star Tamara Bass.

Underwood as Pearl in costume as Scary Spice in 'Little Fires Everywhere.'

Underwood as Pearl in costume as Scary Spice in 'Little Fires Everywhere.'

"All of the women in the movie are still in my life now, especially Miss Meagan Good and Miss Tamara Bass," says the incredibly polite and gracious teen (who was also very patient with my initial Zoom ineptitude). "Being on set with a bunch of women — especially a bunch of Black women — and being able to have freedom of this super complex story about love, friendship, forgiveness and resilience was so phenomenal to be a part of. It was a blast being part of the story."

"I really loved my character, Jillian," Underwood continues. "She's a 15-year-old girl who's a little shy and unsure of herself. She loves football and she's a guru, who can talk about football stats with ease."

Speaking of athletics, Underwood jumped on Zoom from Toronto while filming another dream role: stepping into the, um, shoes of a Disney Princess in "Sneakerella." Set in contemporary New York City, the upcoming Disney+ film gives a progressive, hypebeast update to the age old Cinderella tale, which sees Underwood — who's also looking forward to seeing Halle Bailey and Yara Shahidi take on the iconic Disney roles of Ariel in "Little Mermaid" and Tinkerbell in "Peter Pan," respectively — play the fiercely independent and business astute sneaker scion Kira King.

"Basically, what I love about this role and this story is the fact that we're teaching young girls that you don't have to wait for a man to became a princess," explains the self-professed sneakerhead. "When the story begins, she's already one and a man isn't coming in to save the day. He's not sweeping her off of her feet. I'm excited to spread that message to young girls that you don’t have to wait for a guy to validate you to make you feel special and make you feel like a princess."

Underwood as Jillian in 'If Not Now, When?'

Underwood as Jillian in 'If Not Now, When?'

Outside of filming, Underwood is also an impressive young role model — on top of being a burgeoning media mogul. She kept busy during the spring and summer Hollywood shutdown by growing the production company she founded at age 15, Ultimate Dreamer Productions. She released "We The Voices of Gen-Z," a YouTube roundtable series with a diverse line-up of panelists, including Storm Reid, Eris Baker of "This Is Us," and her "Little Fires" co-star Jade Pettyjohn

While creating a platform for fellow Zoomers to tell inclusive stories and discuss issues important to them, Underwood also appreciates her cohort's use of fashion and style to make a statement: "We're taking inspiration from so many other generations. A lot of the same trends that were big in the '80s and '90s are coming back now. We're just being very free and unapologetic to the choices that we make, especially when it comes to fashion. I hope that future generations are going to come back and look at our stuff and be like, 'Hey, that's cute. Let's bring that trend back.'"

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But in the meantime, Underwood shared why Aaliyah and Rihanna are her biggest style inspirations, which resale sites she scours to bring back '90s style in her own way and what she loves about the season's hottest throwback trend: flared yoga pants. Read on. 

Underwood at the 13th Annual Essence Black Women In Hollywood Awards Luncheon in February 2020. 

Underwood at the 13th Annual Essence Black Women In Hollywood Awards Luncheon in February 2020. 

"I'm constantly drawing inspiration from different people from different generations and different things I see on TV. My biggest style inspiration is Aaliyah, ever since I was younger. I was always infatuated with her. I'm drawn to real people, people who are just super down to earth. They don't have to try or do a lot to be seen or to be depicted as a certain way, and Aaliyah was so effortless. There was something about her and her energy. She was so authentic. That's why she was just genuinely one of the It girls back in the '90s and early 2000s. Just because of her energy and her aura. So I love her — and her music is phenomenal — so she's probably one of my biggest inspirations and it would be an absolute dream come true one day to play her in a biopic.

"[I also look to] Rihanna. She's the Aaliyah of our generation now. She's just so effortless. So authentic. It's the same thing about Aaliyah. There's this ongoing joke [saying] certain fashion pieces don't look good until Rihanna puts it on. All of a sudden when Rihanna puts it on, it becomes this big trend. She's just constantly transcending all areas. She doesn't put herself in a box. She doesn't limit herself and that's what I love about her. She's not afraid to be bold and she's very comfortable in her skin.

"If you watch Rihanna and her Savage x Fenty show, she used fashion as a way to also say: 'Hey, diversity matters. Representation matters and models can come in all different shapes and sizes.' Especially when it comes to fashion, representation and diversity, I just love how all those different ideas meet and what people are creating out of it. I draw inspiration from people who are using fashion to create these wonderful statements.

"I don't know how to properly classify my fashion life, but it's cute and it's comfortable and I'm still trying to figure it out. Try new things. When it comes to figuring it out, my style is still out there. There are some days where I look like a 12-year-old. I can literally dress in super baggy sweatpants, baggy sweatshirts and hide my face. That's so comfortable. I love that kind of style. Then there are other days where I will pop all the way out. I'll have on some high wedge heels and a cute crop top. I absolutely love lashes and makeup. I'm super into that. Makeup can tie together a whole look. 

"Most of the time, I'm shopping online. My only trepidation when I'm shopping online is hoping that it fits. I'm honestly not big on shopping in-store. Usually my mom will shop in-store for me. Or she'll FaceTime me and be like, 'Hey, do you like this?' But other than that, I love just being in my bed and going on different websites.

"I let items stay in my cart for a little while. I like to sit on it, think about it and then buy it. I really love this brand called I.Am.Gia. I have a couple pieces from them in my cart that I want to purchase. The cool pants. The black yoga flared pants with the ties on them. It's the same thing about being comfortable, yet chic at the same time. They're super soft. You can stretch in them. They're not tight or anything. Just the flare at the end adds that aspect of 'I'm comfortable, but I'm still cute.' It just elevates the look. It's versatile, in my opinion.

"I also like shopping on PrettyLittleThing, Forever 21, Fashion Nova. Those type of places. I'm really into Tory Burch when it comes to accessories. I love Telfar. When it comes to my shoes, I absolutely love Jordan 1s. Air Force 1s. Adidas. Diesel. The new Beyoncé collection with Adidas came out recently, so I got some stuff from there. 

"I also love shopping on Depop and Poshmark and doing little thrifts for hidden finds. I really am into the vintage crewnecks. I recently just got some flared yoga pants on Depop and I have bedazzled sweatpants in my cart right now. [Note: Underwood confirms, with a smile and a nod, that it is, in fact, a pink velour Juicy Couture tracksuit with 'Juicy' written in rhinestones across the butt.]

"I love to be comfortable, but chic and trying to stay warm because I'm in Canada right now. Especially because it's winter, I've been super into my Jordan 1s. A good pair of sweatpants or baggy jeans. I love Good American sweatpants and sweatshirts. A good crop top and a nice warm jacket and some hoops and some natural makeup. I've been using all my skincare by Fenty. All Fenty when it comes to makeup. Moose Knuckles just gave me this awesome awesome coat that I'm obsessed with, and Ugg sent me boots. So it looks like an Ugg slide, but it's a wedge and it has a strap on the back and they are so cute, warm and cozy. That's my go-to lately.

"We wrap up production on 'Sneakerella' in a week. Most of my costumes are actually sneakers, which I'm very happy about. Because there are scenes sometimes where people are in tall tall heels and I'm like, 'Ooh, I'm glad I got my sneakers on.'"

This interview has been edited and condensed for clarity.

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