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.
-
I've Worked in Fashion for 15 Years—Here's What I Actually Wear Every DayTrends come and go, but my everyday wardrobe is made of pieces that feel like me.
-
I've Been a Celeb Aesthetician for 40 Years—How I Prep My Clients for the Red CarpetSabrina Carpenter and Phoebe Dynevor's aesthetician, Joanna Czech, shares her must-haves.
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025Everything is under $100.
-
All of the Coolest People I Follow Just Bought Into This New Fall Denim ShapeNo, it's not barrel, wide leg, or bootcut.
-
EverythingBest Knockoff Luxury Clothing Editors Saw, Wore, Did, and Ate During NYFWLet's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to HerA glimpse into the life of this savvy entrepreneur.
-
This Just In: The Denim Wash That's About to Dominate Every Cool Outfit This FallWill you love it or hate it?
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in FallAnd you probably already own it.
-
I Just Started Investing—31 Chic Pieces That Will Have Me Dressing the PartEffortless and elevated is the goal.
-
Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With JeansAs seen on Jennifer Aniston.
