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Reading: Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen — What to Wear!
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Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen — What to Wear!

Last updated: July 23, 2025 11:57 am
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Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen — What to Wear!
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Getting dressed used to be simple. We’d throw on a skinny jean and a longline blazer, or perhaps a floral tea dress teamed with some loafers and a waist-cinching belt, and feel like that girl.

Now? We try what feels like a modern take on the winning looks from our past, and it’s chaos. Step out in a midi dress and crisp white sneakers (like those favored by elder millennials Princess Kate and Meghan Markle, both 43), and Gen Z thinks we’re so cliché. And if we dare to nonchalantly throw a faithful denim jacket over the top, they recoil like we’ve shown up in a Juicy tracksuit and Crocs (both of which they also claim ironically now).

Millennial women are stuck in a fashion vortex: too old to be on-trend, too young to be invisible. Even the biggest millennial stars can’t get it right. Taylor Swift, 35, goes for a red lip and a pair of high-waisted shorts and she’s branded a 2014 throwback — which is, what, a year ago, anyway? Blake Lively, 37, wears a floral co-ord? She’s trying too hard. Chrissy Teigen, 39, gets mocked for rocking hot pants, even though she’s a literal model (but she’s a mom now, and her legs exist solely to be clung onto by toddlers, right?).

Yup, the internet has opinions, and none of them are kind to women who spent 20 years fine-tuning the perfect flicky eyeliner tip, only to be told that’s so millennial. Sandwiched between two generations known for their cool, apparently we’re just basic AF. Plus, we’ve aged into a confusing demographic. Are we supposed to be MILFs, She-EOs, rich moms, hot messes or all of the above?

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If you’re a normal woman out there, just trying to get dressed for the office, your kid’s soft play party or cocktails with the girls (even though the “girls” are grown-ass women now), it’s a minefield. Are we still doing a French tuck or letting our tops hang free? If we dare to wear something figure-hugging, do we look more Kris Jenner than Kylie Jenner? And for the love of God, what the hell are we supposed to be doing with our socks?

Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen —What to Wear!
Princess Kate Samir Hussein/WireImage

It doesn’t help that celebrity street style seems like it’s dead: we mostly see the stars either dressed way down in expensive activewear or way up on the red carpet. The Gen X icons we looked up to for fashion tips in our youth, like Kate Moss in her skinny jeans and Jennifer Aniston in her crisp white tees, are now more like much-loved institutions than present-day style inspo.

Gen Z Crew Socks vs Millennial No-Show Socks: Taylor Swift, Justin Bieber and J-Lo Are Divided!

The other problem? Many of Us were raised on rules dictated by fashion mags and mean TV stylists. Don’t mix black and navy! Match your handbag to your shoes! Now, we have to unlearn it all, as crop tops are inclusive, low-rise jeans are back and clashing is chic if you know how to do it effortlessly. Which we don’t, because from our Instagrammable oat flat white to our three-hour balayage, millennials are all about the effort.

Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen —What to Wear!
Blake Lively Aeon/GC Images

Celeb stylist, “School Runway” podcast cohost and proud millennial Bronagh Meere says we shouldn’t let the so-called rules hold us back. “I’m forever telling people to wear what makes them happy because if you feel good, you’ll look good!” she tells Us. “Don’t worry about what other people think; it’s how you feel that matters. Fashion should be fun, so play dress-up with your clothes, be creative and dress for joy whether it’s for the school run or that rare night out.”

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Stop Telling Millennial Women — Like Taylor Swift, Blake Lively and Chrissy Teigen —What to Wear!
Chrissy Teigen and John Legend Matthew Stockman/Getty Images

Yes! We want to feel stylish, not silly. Cool, but not cringe. Hot, but not trashy. We want to be seen, but not ridiculed. We want to live in a world where we never have to ask the group chat, “Am I too old for Reformation?” when frantically googling outfits for a baby shower. If side-parting our hair, hoiking our jeans up to our bra and cinching our waists makes us feel good, we’re going to keep doing it. Just no ballet flats — it makes our plantar fasciitis flare up.

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