Katie Holmes dusted off some terrible Y2K fashion for a Jingle Ball event

Here are some photos from Friday’s iheartradio Jingle Ball red carpet. People were freaking out about these Katie Holmes photos all weekend, but I’d like to discuss them in the sartorial context of some of the other people in attendance, namely Dove Cameron, Demi Lovato and Dua Lipa. When the Katie Holmes pics went viral, people were like “wow, what a Y2K look” and “this is not it, Katie.” While that’s true – and the jeans are so, so bad – what’s also true is that we are in a very real ‘90s fashion revival.

So much of what I’m seeing on the younger people is from the micro-fashion era of 1998-2003, when Britney replaced grunge-alt, when people wearing dresses over jeans went mainstream, the mainstreaming of ‘90s vampire-goths, the proto-Juicy Couture era becoming the mainstream high-fashion sweats era. It was a chaotic and terrible time. I don’t want to go back to it, but it’s fully back. As I said, look no further than the other people at this event. What Dove Cameron is wearing is how Mark Wahlberg dressed all the time in that micro-era. Demi Lovato is doing Janet Jackson-Rhythm Nation. Dua Lipa is doing mainstream goth.

Anyway, Katie could have pulled this off if A) the jeans were better or B) she had worn black palazzo pants with the terrible top. I have no real comment on the sneakers, I bet they were comfortable. Katie has always had such weird style, but I applaud her for trying different sh-t. Or dusting off some of her Dawson’s Creek-era stuff.

Photos courtesy of Jordan Hinton / Image Press Agency / Avalon.

You can follow any responses to this entry through the RSS 2.0 feed.

30 Responses to “Katie Holmes dusted off some terrible Y2K fashion for a Jingle Ball event”

Comments are Closed

We close comments on older posts to fight comment spam.

  1. DouchesOfCambridge says:

    Katie holmes had weird style and I always enjoy her outfits because they seem personal and not curated by stylists. She’s always over the top in strange and unexpected ways. I prefer that to boriiiiiiing

  2. Abby says:

    So Katie Holmes in jeans and sneakers and the person in the black formal dress are at the same event? Wild.

    This era of fashion was fun and chaotic, as long as nobody makes low rise jeans the only option I can buy, I’ll be ok. I still wear skinny jeans, but I wouldn’t mind wearing flared jeans and a flowy top again. But not with sneakers like this!

  3. girl_ninja says:

    Everyone here looks unfortunate including Dua.

  4. SarahCS says:

    While I want no part of it, the 90’s revival has been visible in the UK for some time now and I’m enjoying watching it on the youths (I was a teenager in the 90’s). I prefer the full on 90’s to this Y2K look though.

    • Tiffany:) says:

      I wouldn’t call this a Y2K look, though, as no one wore this kind of thing then.

      Dresses over pants were done proportionally, with the top being loose and flowy and jeans were bootleg with the thigh being slim cut. In the true Y2K kind of look, volume of each piece balanced out. The cut of the dress here is allllll wrong for that kind of layering. It is too tight at the bottom and so incredibly unflattering.

  5. Janey says:

    Ah man I loved the 90s. I did not wear any of that though. How people so attractive can make themselves look terrible is beyond me.

  6. Greeneyedgirl says:

    I remember this era of fashion…the low rise flare jeans, with the long flowy tops and usually pointed heels. I’m happy this fashion is making a comeback actually. I still have jeans from around 2008 (don’t judge me) and I wear them. I actually prefer low rise over high rise jeans. I find high rise jeans super uncomfortable and very unflattering (on me).

  7. FYI says:

    What Katie Holmes is wearing is objectively terrible. As in “girl, are you okay?” terrible. It is very odd that this is referred to as “style” in any way. The bodice of the dress, the baggy jeans, the ugly trainers — she doesn’t know what she’s doing. At all.

    • shanaynay says:

      Yeah, it’s absolutely horrible!!!! I’m still not understanding why she’s still a thing. I’m so over her.

  8. Susan says:

    I enjoy Katie Holmes. I do. But talk about someone who gets a lot of press and hasn’t done much lately? Her PR people are the best in the business!

    Also, re Y2K fashion: I am terrified. Those low waisted pants were horrifying the first go round when I was young and thin-ish. I cannot fathom what they will be with a midlife pouch, and a C-section scar. Shudder!!

  9. Plums says:

    this is the first I’ve seen of these photos of Katie Holmes, and I instinctively, audibly exclaimed “What the fuck?” upon seeing them.

  10. Blinx says:

    To be fair to her, she’s aged so well I initially thought the photo was taken in Y2K…

    • Anita says:

      Yes, she really did! My first take was – yikes, those pants, then – oooh, but she looks good.
      LOL.

  11. goofpuff says:

    This would have worked well with a different jean with this dress or a different dress with this jean. obviously she did this on purpose so people would talk about her.

  12. Scarlet Vixen says:

    Katie Holmes looks like she thought she’d only be photographed from the waist up. Those jeans–and especially the SHOES–scream, “Noone is gonna see my bottom half so I’ll just leave my comfy old ‘taking the dogs out to pee’ stuff on.”

    • Alarmjaguar says:

      So, what you are saying is that this is a Zoom call outfit, party on the top, comfy on the bottom 🙂

  13. lucy2 says:

    I do not like Katie’s outfit, but I am all for comfortable shoes on the red carpet!

  14. Pocket Litter says:

    They all look ridiculous.

  15. OldLady says:

    I do not know who Dove Cameron is but I love that hoodie it looks cozy and comfy. I think she looks great.

  16. Bella says:

    Katie’s outfit is awful. It looks like she rolled out of bed and put on whatever was lying on the floor.

  17. Kirsten says:

    I wouldn’t even wear her outfit if I was staying inside my house.

  18. Case says:

    I get what Katie was going for, in her own weird way, but the entire outfit is so poorly fitted that it’s a huge fail.

    Demi and Dove look like they’re wearing costumes. I feel like Dove usually dresses better than that.

  19. Caitlin says:

    terrible outfit but she looks great from the waist up. her skin looks flawless and her hair like this is perfection. this really could be a pic from her dawsons creek days

  20. AnneL says:

    My daughter is into the Y2K stuff right now. She’s 25. She would not wear what Katie is wearing here, though. The top, sure, but not with those jeans or sneakers! It looks awful. Katie looks great but the outfit is a disaster.

    The woman on the bottom in the black dress looks fine to me? The cut would look bad on many people, but she’s young enough and petite enough to pull it off. I kind of like the extra straps.

    I hate the others. I suppose they’re fun looks but they’re soooooo unflattering. They look like costumes.

    The low rise-jeans and Paris Hilton-esque denim micro-minis are back big time! I sell vintage clothes on Etsy and the minis in particular sell well. I stopped buying jeans to sell because the site is saturated with them right now. They also weigh more and cost more to ship.

    I personally don’t get wearing either very high-waisted or very low-waisted jeans. Neither is comfortable or flattering to me. But younger people seem to have fun with them, and I enjoy finding things other people like.

  21. Elsa says:

    Her styling is always awful.

    • L4Frimaire says:

      This is such a terrible half dressed look. Her hair doesn’t even look brushed. If this was deliberate, she needs a stylist. Why Katie,why?

  22. J says:

    That outfit sucks. I don’t think that even would’ve flown when it was supposedly in fashion

    She herself looks cute and can pull off a lot but nooooo Katie not this

  23. cf86713 says:

    This outfit wouldn’t be so bad if she wore a dark blue jean jacket and matching jeans. Would be very Joey Potter esque.

  24. Joanna says:

    Katie has the goods but she doesn’t know to dress to show it off. Please get her a stylist