Ten Movies to Watch for Y2K Fashion Inspiration

Believe it or not, the Y2K aesthetic, a term that encapsulates the years between 1998 and 2003, has made its comeback in the fashion world. This was the era of velour sweatpants, low waisted and flared jeans, and bedazzlement galore. Nothing about this period was subtle or natural: artificial highlights, spray tans, and loud makeup was the everyday norm. Brands like Juicy Couture, Von Dutch, and Ed Hardy ruled the fashion world. 

While these vibrant trends and iconic brands have been slowly creeping into the fashion scene over the past two years, they have now officially taken it over. Maybe it is because people had newfound time to watch classic 2000s rom-coms over quarantine, or maybe it is a result of people diving through old clothing bins to resurrect key pieces during months spent at home. Or, because fashion always seems to be looking 20 years into the past for inspiration, perhaps this return is just the inevitable outcome of the turn of the decade (perhaps 2020’s one redeeming moment). I mean, the 70s looked to the 50s (Grease), the 90s looked to the 70s (That 70s Show), and the 2010s looked to the 90s (think: the now-fading obsession with mom jeans and crop tops). Since we recently moved into a new decade, it checks out that we are now turning to the early 2000s, the aesthetic that was all the rage exactly 20 years ago. 

Once you accept that Y2K has conquered the contemporary trend radar, you may want to know how to achieve the look. Thankfully, there is a super easy and entertaining way to get to know this trend: early 2000s movies! Watching movies that were filmed in the very late 90s and early 2000s is the best method to learn what this period was all about. It’s the ultimate research assignment. Here are the top ten movies to watch for Y2K inspiration:

The Hot Chick (2002)

hotchick.jpg

The Hot Chick is a hilarious movie about a Freaky-Friday-esque switch between a vicious highschool girl and a grimy crook. While the movie did not receive renowned praise nor did it age particularly well (some of the lines are pretty cringe-worthy), the Y2K outfits are impeccable. The romantic comedy makes a strong case for floral halter tops, colorful baby tees, and teeny tiny skirts. But be warned: do not watch this movie if you are still in denial of the inevitable return of extremely low-rise jeans.

Crossroads (2002)

crossroads.jpg

I am not mentioning Crossroads for its intriguing plot (because it doesn’t really have one). However, this iconic movie had to make the list due to the amazing outfits worn by the Y2K queen Ms. Britney Spears. When I think of the early 2000s, Britney immediately comes to mind. She championed tiny jeans paired with tiny tops and iconic matching sets. So with Britney as the lead, you will inevitably walk away from Crossroads with all the Y2K inspiration you could desire.

Freaky Friday (2003)

freakyfriday.jpg

Another Y2K fashion pioneer is the influential Lindsay Lohan. Lindsay delivers amazing fits in Freaky Friday. Her heavily-highlighted red and blonde hair is iconic. And how could you forget the red and black band tee (a piece that is also worn by her classmate, awkward!) paired with low-waisted, loose-fitting green cargos. If you are looking for some punk or rock-inspired Y2K looks, turn to Linday’s two band friends for inspiration. You won’t be disappointed. 

Bring It On (2000)

bringiton.jpg

While the Bring It On outfits are definitely noteworthy, there are so many reasons to watch this cult classic. From the timely social commentary on cultural appropriation to the energizing cheerleading stunts to the hot Jesse Bradford, Bring It On is a must see. Let’s face it, the leads in most early 2000s movies are predominantly thin, white women. And while Bring It On has no shortage of those, it is a refreshing change of pace to see the movie’s diverse cast. And this diversity allowed the costume designers to showcase trends that were started by the Black community. Look to Bring It On for inspiration on how to wear Y2K logomania, curly hair, and hoop earrings.


John Tucker Must Die (2006)

johntuckermustdie.jpg

Despite coming out a couple of years after the Y2K heyday, the marvelous outfits in John Tucker Must Die cannot go unmentioned. Ashanti’s low-waisted, white pants and teeny orange crop top stand out as a look to remember. The movie also showcases the gingham halter top, a Y2K must-have. And regardless of the looks served, I had to include this movie for its hilarious pranks and strong female power.

Coyote Ugly (2000)

coyoteugly.jpg

Coyote Ugly is a true fashion gem. From the low-waisted leather pants (a piece that I have been on the hunt for for the past six months), to the endless cheetah print, to the silky halter tops, the outfits in this classic make an unforgettable impression. The movie is also full of energizing dances, strong female friendships, and bar scenes that will make you wish quarantine was over even more than you already do. Plus, there is young Tyra Banks. 

Thirteen (2003)

thirteen.jpg

To learn how to be a Y2K “bad girl,” watch Thirteen ASAP. If I was as cool and angsty as the two lead characters in Thirteen are when I was thirteen, who knows where I would be today. Decked in looks that I yearn to wear as a 21-year-old, the tween girls in Thirteen provide endless fashion inspiration. Their bedazzled jeans end inches below the belly-button, their tops are full of grommets and holes, and their grunge makeup is effortless and cool. 

How to Lose a Guy in 10 Days (2003)

howtoloseaguyin10days.jpg

I know the characters in this film are perhaps a bit older than the influencers you might normally turn to for fashion references, but the women in How to Lose a Guy in 10 Days deliver. Kate Hudson’s outfits provide perfect Y2K inspiration for any occasion - from the silky halter dress she wears on her first date with McConaughey to her stylish office looks. This list would not be complete if I failed to mention Hudson’s iconic yellow dress, which holds a special place in my fashion-obsessed heart. 

Ghost World (2001)

ghostworld.jpg

The Y2K looks that women in early 2000s rom-coms serve are often extremely feminine, sweet, and form-fitting. But the Ghost World outfits provide a refreshing glimpse into the era’s grunge scene. A bit more in touch with a ‘90s minimalist vibe, the outfits are simple and cool. Scarlett Johansson wears a lot of monotone pieces while Thora Birch dawns screen-printed tees and dark plaids. I love Ghost World because of its cool angst, relatability, and accurate depiction of small town life.

The Simple Life (2003 - 2007)

Screen Shot 2020-10-07 at 8.46.15 PM.png

I know The Simple Life is not a movie, but I could not not mention this iconic television series. When I think of the early 2000s, two names that immediately come to mind are Paris Hilton and Nicole Richie. These two ladies pioneered velour sweatsuits, Von Dutch trucker hats, and “skunk hair.” I spent all of quarantine rewatching this amazing television series and was blown away by the outrageous and mesmerizing outfits. The first two seasons provide endless Y2K fashion inspiration. If you are looking for new fits or are simply looking to laugh out loud, check the show out. 

I hope these iconic movies provide you with the necessary inspiration to rock a Y2K look. Happy researching


All Images from Google Image and Pinterest

Mia Risherbatch 2