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Before teens decorated their bedrooms with string lights and polaroid prints from Urban Outfitters, walls were plastered with posters from magazines. I had a shrine to Hilary Duff in my room, wore my hair in spiked buns and carried a Hello Kitty CD player everywhere—it was the early 2000’s and fashion was funky and fun. Last night, Olivia Rodrigo’s MTV Movie and TV Awards look brought me right back to my childhood bedroom. Rodrigo was a walking time warp between her halter top and zig-zag part. Olivia Rodrigo won MTV’s Best Documentary award for her short film driving home 2 u and per usual, she won a “best dressed” stamp of approval from me. 

Like a true Gen-Z It-Girl, Olivia Rodrigo is obsessed with early 2000s and Y2K trends. Ironically, 19-year-old Rodrigo is channeling an era in which she primarily missed out on (she was only three years old in 2005). Her overall styling of the look was in line with the typical Y2K/2000’s choices Rodrigo makes with strappy kitten heels, fringed hair buns and metallic silver nail polish. Though her dress looks like it could’ve been a product of the Simple Life era, it’s actually a piece from the ‘80s. 

STYLECASTER | Olivia Rodrigo MTV Awards Look

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Rodrigo’s tight bustier dress is a Jean Paul Gaultier dress from 1987. The dress has a form-fitting silhouette down through its ankle-length hem which gives it a mature look. On the contrary, the leather corset paneling and silver zipper help give the ensemble a younger, more daring feel. 

In an interview with Vogue, Olivia Rodrigo’s stylists, Chloe & Chenelle Delgadillo talked about the power of the dress’ feminine silhouette and said, “For a fresh take, we crisscrossed the straps in the front, which made the look feel a bit younger.” 

STYLECASTER | Olivia Rodrigo MTV Awards Look

The Mega Agency.

For beauty, Rodrigo matched metallic eyeshadow to her manicure but otherwise kept the look very natural. The light makeup look fits Rodrigo’s latest partnership with Glossier—she was recently announced as the new face of the “no-makeup makeup” brand. The partnership taps into Rodrigo’s influence to help garner relevance amongst younger consumers.

STYLECASTER | Olivia Rodrigo MTV Awards Look

The Mega Agency.

Rodrigo typically opts for moodier red carpet looks, so her Jean Paul Gaultier dress wasn’t a departure from the norm. At this year’s Grammy Awards, Rodrigo wore a tight black and pink Vivienne Westwood gown and delivered a perfect hybrid of Disney star turned punk-pop princess. Though her Westwood gown wasn’t vintage, it did pay homage to the recent revival of the ‘90s designer (which was primarily driven by TikTok). 

Even on-stage, the singer is able to incorporate nostalgia into her performances. She recently brought Avril Lavigne and Alanis Morissette on stage to sing a duet of their hit songs. When Olivia Rodrigo isn’t playing sold-out shows across the country or walking a red carpet, she is often spotted vintage shopping out with friends (often in a vintage ensemble). She is able to bring old pieces into her wardrobe to set new trends (yes, Rodrigo was the reason I finally bought a plaid mini skirt). I can’t wait to see what she repurposes next. 

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