Celebrities are known for really pushing the boundaries and really going for it, regardless of the “fashion rules” out there. This is particularly true when it comes to embracing their denim looks. In fact, while recently covering the skinny-jean styling “mistakes” A-listers make, we realized that celebs in their 20s are most notorious for wearing skinnies in more unconventional ways.
You may remember Hailey Rhode Bieber’s scrunched skinny jeans and ankle boots here when she was out and about in NYC. Well, there’s a slew of others that are following suit, including Jasmine Tookes and Gigi Hadid. Okay, okay, you’re probably ready to see these mistakes in action, so keep scrolling to see how 20-somethings own their denim looks and shop some of the coolest pairs of skinny jeans if you need to refresh your offering. And remember, there’s no such thing as dressing for your age, so get inspired by the below ’fits no matter when your birthday falls.
"Mistake": Stuffing cuffed jeans into boots
Stuffing jeans into ankle boots used to be a don't, but Hailey Rhode Bieber continues to prove the look (even with rolled up denim) is quite forward now.
"Mistake": Going for skinnies with strappy heels during the day
Jasmine Tookes is never afraid to wear what she loves no matter where she is, like opting for a denim ensemble that feels more nighttime during the day.
"Mistake": Allowing skinny jeans to bleed into sneakers
We tend to see people wearing cropped jeans with sneakers to break up the two pieces for a cool look, but Lucy Hale proves that's not totally necessary.
"Mistake": Wearing skinnies with just a pullover
Sometimes it's okay to just keep it simple and not worry about incorporating layers upon layers for a high-concept vibe. Right, Dakota Johnson?
"Mistake": Going for extreme cropped jeans with heels
While taller ankle boots would work with Karlie Kloss's ensemble to fit with her extremely cropped jeans, showcasing the full ankle with kitten heels actually feels quite polished.
"Mistake": Not switching up the color palette
Celebs like Gigi Hadid are never scared to go for the monochromatic look—even with their denim outfits like this blue skinny jean 'fit.
Shop more skinny jeans:
Next, check out more skinny jean styling mistakes celebrities make.
-
The Numbers Don't Lie: This Is the Only Denim Trend More Popular Than Baggy Jeans Right NowAccording to data.
-
I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds From Nordstrom, Zara, and H&MDid I mention they're under $250?
-
I'm 5'0"—These Are the Only Jeans That Get My Petite ApprovalThe hunt is over.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall ClosetStylish sweaters and suedes ahead.
-
Abercrombie Sucked Me Back Into Its Orbit With These 25 Incredibly Chic Fall 2025 FindsSo, so good.
-
People With Impeccable Taste Swear By COS—21 Chic Sale Finds to Take Advantage of Right NowDid you say 25% off? Yes, please.
-
The 6 Shoe Trends Well-Dressed People Are Wearing With Pants and Jeans (Instead of Sneakers)Flat and heels to pair with pants and jeans.
-
I'm a Fashion Editor on a Budget—27 Incredibly Chic Fall Finds That Will Get You More Bang for Your BuckStellar under-$150 finds right this way.
