“The Worst Trend of the 2000s”

Paris Hilton in a dress over jeans, mid 2000s. 

In December of 2022, Katie Holmes single handedly made dresses over jeans mainstream, again. Holmes stylist, Brie Welch, endured a lot of hate for the look, with comments like “The worst trend from the 2000s is back!”. Welch quickly silenced the haters by saying, “Women should be able to feel fancy and casual and comfortable all at once. This is what I have done here” (AMEN SISTA, SAY IT LOUDER FOR THE LOSERS IN THE BACK). However, Holmes is not the first person to revive this trend since its hold over 2000s red carpets and pop-culture. First made popular by Disney Channel stars in the late 2000s, the trend was quickly adapted to streetwear and fast fashion brands of the time. In the blink of an eye, rockstars had adopted the trend, and kids were wearing it to school. It truly dominated the industry, before losing popularity with the birth of Tumblr and Indie Sleaze. Versions of dresses over pants were seen in the Twee movement, Grunge, and in 2016 when everyone wore leggings (or jeggings) under quite literally everything. And then, Rosetta Getty showed a white shirtdress over black trousers for Fall of 2021. In November of 2021 Lizzo and Hailee Steinfeld put their own twist on the trend; Lizzo wearing a fuchsia mini dress over jeans and Hailee wearing slacks under her Richard Quinn dress at the Hawkeye premiere. It hit the runways again for Spring 2022 when designers like Rachel Comey and Louis Vuitton experimented with monochromatic colors and slip dresses. Chloe showcased the trend in leather for Fall 2022. And most recently, designers like Colina Strada, Proenza Schouler, Sacai, and Chopova Lowena showed some version of dresses over pants as part of their Spring 2023 collections.

Katie Holmes at the 2022 iHeartRADIO Jingle Ball.

If this trend is not so new, then why did Holmes and Welch’s take on the trend have so many people up in arms? I think it’s because the look made a little too much sense to their… pea sized, brains. But that’s just my opinion. In all seriousness though, when Katie stepped onto the red carpet in a strapless, navy blue, Tove mini dress, Reformation Jeans, and Maison Margiela sneakers, it felt like my childhood had returned to me. My days of jeans under skirts and dresses, following in the footsteps of Kelly Clarkson and Ashley Tisdale, were no longer behind me but, in front of me. In most every picture of me between the ages of 7 and 10, I am wearing some kind of pant under some kind of skirt. It made me wonder, why did I ever stop wearing a style that was so personal to me for such a long time. The only logical answer seemed to be anxiety and a need for validation. In middle school I fell into the trap of Forever21, American Eagle, and Pink. I ditched the sense of style I had spent my entire childhood cultivating, all so kids wouldn’t make fun of me. Looking back, people liked me less when I acted like someone I wasn’t. After much contemplation and stressing over whether or not I would look stupid, I wore a dress over jeans. Easily the most liberating thing I have ever done.

Me, age 10, at camp... my mama took this picture:)

The outfit was brewing in my head for what I would call many, many weeks. The vintage, silver sequin mini dress in my closet tempting me everywhere I went. I finally gave in. I paired the dress with a pair of light-wash jeans from the Urban Outfitter’s clearance rack (I bought them 4 years ago in Portland… #slaying), and my Anine Bing trench coat. I wanted my look to be timeless, casual, and put together for class but, I also wanted to make a statement; “Fuck yeah, I am wearing jeans under my dress! What about it?”. I tied the look together with my FAVORITE shoes, a pair of green suede mary-jane ballet flats (brand is Coclico). Wearing the outfit made me realize the immensity of misconception around styling and trends in the industry. For so long I assumed that if I wore a dress with jeans people would think I looked silly or would question my authority as a hard-working fashion woman. The response was truly quite the opposite. I got called bold and timeless. My professor told me “Wow, that dress on you. I love it.”, paying no mind, or care, to the jeans that lie beneath it.

So how is wearing a dress over pants “the worst trend of the 2000s”? I mean we all remember low-rise skinny jeans, cheetah print everything, and converse boots… right? Anyway, if I had to guess, I would say the fashion statement is unpopular because many simply lack the guts to just wear it. I called one of my best friends from home while I was trying to figure out shoes, and before he said anything, I warned him that my outfit was a little “out there”. When I showed the outfit, he commented on how it was weird, and how it shouldn’t make sense, but it somehow did. To be frank, I think it only worked because I wanted it to. I was ready to just step out in the sparkly dress and super comfy jean combo. For the first time in a long time, I knew that I loved the outfit regardless of the opinions of others. Dressing for myself is not something I thought would ever happen and yet here we are. The media tends to put stars in the spotlight for their bold clothes and memorable outfits, but not often enough do they recognize the emotional impact some of those fashion moments can have on the people that see them. Anne Hathaway, Jessica Alba, and the Olsen twins didn’t stunt on the red carpet in dresses over jeans just for the media to be hypercritical, and for Forever21 wearing on-lookers to pick fun at their moment. They were simply showcasing a style they connected with, felt comfortable in, and LIKED. I say all the more power to them. Isn’t that what we should all be doing when we’re getting dressed? Next time you want to wear a dress over pants… do it.

-Miss O

Jessica Alba, Devon Aoki, The Olsen Twins, Ashley Tisdale, Anne Hathaway, Kelly Clarkson, Mishca Barton, and Rachel Bilson.