8 “Cringey” Millennial Fashion Trends That Aged Horribly
Millennials are defined as being born between 1981 and 1996, but if you were born at the tail end of that time frame and endured your teenage years during the 2000s or early 2010s, you most definitely suffered through some arguably rough fashion trends.
Wearing Abercrombie or Aeropostale brand name t-shirts, sporting chevron dresses, and going to parties with “concealer lips” was (regrettably) the vibe at the time! Today, most teens wouldn’t dare wear the outfits and accessories us millennials wholeheartedly loved.
We’re here to revisit fashion’s past and call out the top 8 millennial style fails that are just super cringeworthy today.
1. Flower Crowns
Etsy
Rainbow Flower Crown
When millennials wanted to look ‘boho chic,’ they immediately busted out the flower crowns. This accessory infiltrated practically every occasion, from high school dances and music festivals like Coachella – or even (sigh) regular trips to the mall.
While the trend might’ve felt fun and carefree at the time, flower crowns are super cliché today and just remind me of Tumblr’s heyday (IYKYK).
2. “Geek” Glasses
Amazon
Black Nerd Glasses
It’s funny to think about how popular wearing fake “geek” glasses was, particularly since so many teen movies of the time, like Mean Girls, sensationalized being “cool” and “popular.”
Nonetheless, plenty of millennials set out to appear quirky by topping off their outfits with thick, oversized hipster frames, even if they didn’t actually need glasses. Some people even used their leftover 3D glasses from movie theaters and simply popped the lenses out – guilty!
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3. Hair Feathers
Etsy
Feather Hair Extension Clip
Similar to flower crowns, hair feathers emerged as a bohemian-inspired way to add a pop of color and texture to your locks. Some people opted for thinner solid or multicolored strands; meanwhile, others went full-throttle with larger feather shapes or even bead attachments.
This is another “hipster” trend that, while maybe still appropriate for some music festivals, should stay in the past when it comes to everyday wear.
4. Jeggings
Halara
Halara Flex High Waisted Stretchy Leggings
Jeggings were supposed to be the perfect blend of comfort and style… or so we thought. The idea seemed genius at the time, but in retrospect, they were just a fashion mistake.
This pant style attempted to blend two completely different types of garments and created a result that’s now considered a fashion faux pas. Jeggings are just too tight to ever be flattering and don’t deliver that same classic denim look.
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5. Converse Sneakers With Anything
Converse
Converse Chuck Taylor All Star Canvas Sneakers
Skinny jeans, skirts, maxi dresses, and mini dresses. Today, you’d probably pick different shoe choices for all of these outfits, but millennials undoubtedly had a go-to: Converse.
These sneakers were the perfect footwear for practically any look, but the trend quickly became overused. Even celebrities were showing up in low-cut Converse to walk the red carpet, a statement that would leave younger generations scratching their heads today.
6. Belts Over Shirts
Amazon
Grommet Leather Belt
Along with the excessive layering of tank tops and t-shirts came the addition of belts on top. While this might’ve been an attempt to add some structure or flair, many belts in the 2000s were more clunky than chic.
This trend is making a comeback, particularly with oversized outerwear. But, again, younger generations today are making more pattern- and color-conscious decisions (and not just cinching their waists while wearing Hollister v-necks, LOL).
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7. Ombré Hair
Polina Semernina / PEXELS
Ombré hair is often associated with balayage, a hair-painting technique that remains insanely popular in 2025. However, many millennials didn’t hit the salon to achieve their ombré – and took matters into their own hands at home.
Regardless of whether they tried to darken or lighten, it typically resulted in a not-very-well-blended horizontal line of color across their hair.
8. Fedoras
Julia Volk / PEXELS
Finally, I believe that you should be entitled to compensation if you’ve been personally victimized by a fedora. Everyone from Justin Timberlake to Paris Hilton wore these hats, making millennials think they were cool. In hindsight, perhaps everyone (including the A-listers) blundered with this fad.
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