I Channeled My Favorite '90s and '00s Movie Style and Have Never Been So on Trend

Updated on 11/30/2019 at 9:50 AM

POPSUGAR Photography | Sarah Wasilak

My boyfriend and I love watching comedies from the '90s and early 2000s before bed at night. We've both seen these flicks hundreds of times for the most part, but if he's trying to introduce me to a classic I haven't watched, I always ask the same absurdly childish question about the film before we start: "What actresses are in it?" Why? It's about outfit inspiration, people! Especially now, when trends like low-slung jeans and going-out tops from the early aughts are resurfacing, I can't get enough of that "grown-up Limited Too look," or so I call it.

"Do I look like Britney Spears at 17?" I've generally started to ask my family and friends (who are not in the fashion industry) before we go out to the movies or a low-key diner for dinner. "Um, yes actually, exactly like that," they say, raising their eyebrows at me like I am a crazy person. "Good, that's what I'm going for!" I assure them.

But as I've run out of Britney, Christina Aguilera, Avril Lavigne, and Gwen Stefani outfits to re-create, I've turned my attention to the screen. After I watched Pulp Fiction for the first time, I dressed in Mia Wallace's sexy, simple black-and-white color palette for a solid week. Why not bring that back when the iconic flares and button-down she dances in would make for a fabulous combination today?

So that's my new method for getting dressed. I've been reminiscing about and rewatching old movie scenes with incredible style moments, then making them feel brand-new with fresh little twists from my closet. Enter Jennifer Garner as Jenna Rink, Rachel McAdams as Regina George, and even Kate Hudson as Penny Lane for a little boho influence (a double throwback to the '70s and '90s!).

Read on to see how I've reinterpreted these signature looks, then leave a note in the comments to let me know which fictional character you want to see me dress like next! What, you thought there'd be a limit to my dedication? As if!

Regina George From Mean Girls, 2004

Regina wears flares and sneakers, and she lets her blue bra straps peek out from under her off-the-shoulder top. That was such a cool little style move back in the early 2000s. Of course, her look comes complete with an initial necklace and designer belt.

I didn't have a sugar-pink Louis Vuitton belt to slip on, but I took Regina's outfit into 2019 with my thin Gucci logo belt in leather.

Cher Horowitz From Clueless, 1995

Everyone seems to remember Cher's yellow checked skirt suit, but I am such a fan of the way she layers a tank over her white tee for gym class.

I added Lucite hoops and slipped into a silk midi skirt (which still feels totally '90s to me) instead of trying on Cher's biker shorts. I did wear this outfit to the office, after all.

Jenna Rink From 13 Going on 30, 2004

Jenna's most exciting outfit is obviously the cutout graphic-print dress she wears to dance to "Thriller."

I just picked up this '90s shoulder bag from Topshop, and it instantly reminded me of Jenna's purse in the movie. I wore it with a quirky, colorful Marc Jacobs dress, but I added Western influence with my Dolce Vita boots. As far as jewelry goes, Jenna might love butterflies, but I'm a fan of shells.

Mia Wallace From Pulp Fiction, 1994

There is something so sexy about Mia's casual combination: a white shirt, unbuttoned at both the top and bottom, with a pair of flares. Mia doesn't wear shoes to dance with Vincent Vega, and her outfit still seems complete to me. I see so many women re-create Mia's look for Halloween — it's that iconic.

Instead of cropped flares, I kicked things off in my favorite wide-leg denim from Mother, and I wore a black headband, just to pay subtle homage to Mia's dark hairstyle. I unbuttoned my sheer top just like Mia does and wore snake-print boots.

Penny Lane From Almost Famous, 2000

OK, so Almost Famous is actually set in the early '70s, but like I mentioned, going-out crop tops and jeans are back in full force, and I personally take inspiration from bohemian fashion moments whenever I can. A young Kate Hudson is also totally representative of the early '90s and 2000s to me — she had the same romantic look in How to Lose a Guy in 10 Days and Le Divorce — so I think this one counts!

I did mix in some groovy tie-dye here, with the help of this Cotton Citizen crop top, but my wide-leg jeans blended both decades perfectly. The silhouette was a salute to the '70s, while the long belt and boot-cut length were details Britney Spears would've favored in the '90s.