I Faced My Fears by Testing Out Every Intimidating Denim Trend From the 2000s

The early 2000s were like the Wild, Wild West when it came to denim. There was no rhyme or reason for why a silhouette would be trending, but nonetheless, it would be. Miniskirts akin to tiny strips of raw denim (worn with, but not secured by, a big belt), baggy styles that slipped way below the waist, and all things bootcut ruled the fashion world. They were worn on repeat by celebrities such as Paris Hilton, Rihanna, and Nicole Richie despite the fact that most of the above completely opposed the primary rules of denim—practicality and comfort. 

WHO: Paris Hilton and Nicole Richie

WHAT: party in Los Angeles, 2002

WHO: Rihanna

WHAT: The Teen People Listening Lounge Party in West Hollywood, 2005

So when early aughts denim faded away toward the end of the decade—making way for straight-leg, classic styles—many were relieved. Finally, jeans that made sense were back in vogue. We stored the aforementioned trends away in a file marked "never again" and went on with our lives. That is until last year when rumors of a 2000s comeback began making the rounds in the fashion world. Suddenly, the trends we swore would never return were doing exactly that. 

Like everyone else who felt bliss at the thought of never wearing low-rise jeans and itty-bitty miniskirts again, I was intimidated by their resurgence. But being that getting ahead of trends is literally my job, I knew I'd have to face my fears head-on, even if it meant wearing a jean skirt so short it should be illegal. That's how I ended up roaming the streets of New York City in a mix of baggy, low-rise, and bootcut jeans, not to mention the world's tiniest miniskirt. Below, find out what I really thought about the above '00s denim trends after trying them on IRL. 

1. Baggy Jeans

WEAR: Prada jacket; Ciao Lucia Bea Top ($64); Zara ZW the Boyboy Relaxed Fit Jeans ($70); Zara Platform Clogs ($60)

I decided to start with the easiest-to-digest trend, figuring that I'd work my way down to the one that intimidated me most. Baggy jeans aren't exactly new to me. I wear a lot of baggy clothes already and actually already owned a few pairs of slouchier jeans ahead of this try-on. Unlike a lot of the denim trends of the early '00s, baggy jeans are almost always comfortable and versatile, making them an easy addition to your modern jeans collection. I paired these oversize jeans from Zara's spring drop with a bra top for balance as well as a vintage men's shirt-jacket and platform clogs. Tip: When opting for baggier silhouettes, I always prefer to wear higher heels and a more fitted top for the sake of proportions. 

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2. Bootcut Jeans

WEAR: Aeron blazer; Closed jeans; Nomasei Lido 35 Pumps ($295)

I actually wouldn't call bootcut jeans all that intimidating. Though, they haven't always been my favorite denim silhouette. I'd much rather wear a straight-leg pair of jeans than a bootcut pair. But recently, the '00s-style cut was worn by Megan Fox as well as a handful of fashion influencers, suggesting that it's going to get big very soon. So of course, it felt important to get out of my comfort zone and push myself to style them. 

Since I'm not used to wearing this more flared style, I wanted to keep the look pretty simple. With my jeans—a darker-wash pair from Closed—I wore a white T-shirt, a cream tuxedo blazer, and red ballet flats for some added color. To my surprise, I actually received a lot of compliments on this look, my jeans especially. Who knows? Maybe I'll become a bootcut fan after all. 

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3. Micro Miniskirts

WEAR: Zara jacket; Urban Renewal Recycled Levi’s Low-Rise Denim Mini Skirt ($49); Zara Flat Knee-High Boots ($90) 

I went to meet up with a group of friends—one of whom was by my side the first time that tiny jean skirts were trending—directly after I picked up my skirt for this story. Their response when I pulled the teeny piece of fabric out of my shopping bag? "Eliza… How?" That was my question too. How could I possibly style this skirt in a way that didn't make me feel uncomfortable given how short it was? Suffice to say, I tried on a lot of different outfit combinations before settling on this one: an oversize denim shacket (I had to play into the Canadian-tuxedo trend of the 2000s); knee-high flat boots; and a baby tee. I enjoyed how the wider cut of the jacket distracted from how minuscule the skirt was, and the high boots made it so that my legs weren't completely out. Again, it's all about proprotions for me. 

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4. Low-Rise Jeans

WEAR: Babaton waistcoat; Zara ZW the Vintage Boyfriend Jeans ($60); Maryam Nassir Zadeh sandals

Everyone loves to tell me that I'm the low-rise-jeans girl, one of the few people they know who actually frequents the early aughts style. And yes, these days, I do prefer a lower rise to a super-high one. But it wasn't always like that. For years, I wore the same pair of ultra-high-rise jeans from Rolla's almost every day (count the appearances in my college photo albums) and swore that I'd never subject myself to low-rise jeans. It took a lot of trial and error for me to change my mind, but eventually, once I'd discovered that low-rise jeans didn't have to be extra tight and have a two-inch zipper, I began incorporating them into my regular rotation. My suggestion: Start with a slouchy pair that naturally sits low on your waist rather than buying a pair that looks like it was actually made in 2003. You'll thank me later. 

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Next: From Ultra-Low-Rise to Exposed Thongs, Welcome to the Y2K Denim Renaissance