Katie Holmes Wore a Controversial Y2K Dress-and-Jeans Look on the Red Carpet

I don't know if Katie Holmes planned to make headlines after her red carpet appearance this week, but make headlines she did. She looked beautiful for her appearance at iHeartRadio Z100's Jingle Ball at Madison Square Garden, and she was also wearing an outfit that was straight out of her early-2000s playbook.
Back in the early 2000s, Holmes was constantly busy with appearances, as one is when they're the star of a hit TV show—Dawson's Creek, of course. The outfit she wore to Jingle Ball took a page right out of her Joey Potter era, and I have the photos to prove it.
For the very recent occasion, Holmes wore a Tove strapless number that was technically a top but could pass as a minidress, especially on someone on the shorter side. While she may have been party ready on the top, she was errand ready on the bottom, opting for baggy jeans and black sneakers. But somehow, she made it work and looked every bit as cool as she always does.
Just for fun, I went back into the Getty Images archives and found a couple of instances back in the early 2000s in which she wore similar tops with jeans on the red carpet. So I think it's safe to say that Joey Potter–era Holmes would approve. Scroll to see the past and present looks and shop similar dress-tops to pair with jeans.
On Katie Holmes: Tove top; Reformation Wilder High Rise Wide Leg Jeans ($148)
Shop Dress-Tops to Wear With Jeans
Next up, 8 Fancy Winter Outfit Trends to Wear With Jeans

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
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