My Style Is Purely Y2K—I Tried 5 Outfits Inspired by the Decade's Greatest Hits

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Gen Z Says is a series where we tap different members of Generation Z who will give us the latest insight on what's cool in the fashion space.

You've probably noticed that many trends from the early 2000s have resurfaced on the fashion scene—loved by some, controversial to others. While most of us may incorporate a colorful piece of jewelry or statement accessory inspired by the era, others have used that time period as a center point for their entire wardrobe and style aesthetic, like our very own WWW Gen Zer Devin Apollon. She showed off her nostalgic style as we kicked off the series, but now we're taking a deep dive into her personal style and why she resonates with the 2000s now more than ever. 

When you think of Y2K style, Paris Hilton may come to mind, but it really is the musical artists of that generation, from Destiny's Child to Britney Spears, who led the fashion trends. Anything those stars wore was destined to become popular alongside their musical hits. To this day, it's hard to think of that time period without singing along to "Say My Name" or "Toxic." To Apollon, that's what that era is all about, which is why she styled five looks inspired by some of the greatest songs of the 2000s that still resonate with her today. Keep scrolling to see her looks that will have you thinking you stepped into a time machine.

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"Let's talk Aaliyah. Gone too soon, that's a fact, but she left an imprint on music, Black film, and R&B history. She also had one of the best (and most underrated) style moments of her generation. Aaliyah was always ahead of her time, and the few music videos she graced us with prove that. This song, in particular, just makes me feel so fresh, airy, and free. It is the musical equivalent of a sip of iced matcha on a hot summer day. It reminds me a lot of certain 'fits I put together when I want to be fresh and free but still cute. If you’re not up to speed on Aaliyah, I suggest you get there ASAP!"

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(Image credit: @devapollon)

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"This song? Princess of flirt activated. Heiress vibes are what I get from this song (and most of Mimi's discography, if I'm being honest). My love for the butterfly motif comes from Mariah. I love that she owns it in such a glamorous way. Mariah owns sexy silhouettes, sheer fabrics, and glitz in her wardrobe. This song is giving me the optimistic, vibrant mood that takes over my body whenever I'm involved in anything fashion. My remix would be called 'Clothes (I Need You)' by Dev."

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(Image credit: @devapollon)

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"Missy? Style icon. Musical genius. End of story. This song has cultural relevance so beyond Mean Girls, and it is an instant classic to me, my family, and so many friends. Stylistically, I have Missy to thank for the influence that baggy clothes, jeans, and sets have on my wardrobe. I obviously love being comfortable, but baggy works sooo well in fashion. My favorite trick is to pair baggy bottoms with a teeny top. It's super flattering and such an effortless look. Balance. Missy also has such a penchant for making hip-hop fashion. It is one of the most daring, yet rewarding, fashion crossovers."

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"If we have any era to thank for the camouflage trend in fashion, it is the early 2000s. (Thank you to the Army and Cady Heron.) Just as influential as camouflage was Destiny's Child, who had a choke hold on us all for the better half of a decade. I'm an original Destiny's Child superfan (which translated to my everlasting love for Queen Bey). Although, when I put these two early 2000s phenomena together, Meagan Good also comes to mind. For me, she is a Y2K red carpet legend and one of the best actresses of her time—independent, talented, and a pioneer of low-rise, flared (camo) pants."

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"Denim is a style essential for me; it is a fabric that I simply could not live without. The best part about it is how sexy you can make it if you choose to. I prefer my denim to be fun and 'Outrageous,' as Britney once sang. This is one of my fave Brit throwbacks, and it just brings me back to the funk and flair of her dancing days. Back in the day, Britney loved a Versace moment, which is the designer responsible for this all-denim number. The song exudes confidence and ownership of one's sexiness, and I cannot help but be obsessed."

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Next: Every Y2K Jewelry Trend That's Officially Happening Again

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.