6 Skinny-Jean "Mistakes" 20-Something Celebs Continue to Make

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.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
It's Now or Never—54 Last-Minute Amazon Prime Day Deals You'll Regret Skipping
Elevated basics, celeb dupes, luxe-like styles, and more on sale.
-
Just so You Know, *This* Is the Denim Trend New Yorkers Wear With Loafers (Sorry, Skinny Jeans)
And they're on sale right now on Amazon.
-
I Shop for a Living—These 30 Elevated Fashion, Beauty, and Home Décor Picks From the Amazon Prime Day Sale Have My Attention
Chic, practical, and affordable.
-
Hailey Bieber Already Wore the Denim Outfits That Will Define Fall 2025
She's always setting the trends.
-
Oh Wow, Hailey Bieber's Go-To Denim Brand Is on Major Sale During Amazon Prime Day
Don't miss out.
-
If a French Woman Shopped the Amazon Prime Day Sale, She'd Instantly Add These 31 Chic Picks to Cart
Effortless and affordable? Yes, please.
-
So Many Celeb-Loved Jeans Are On Major Sale RN—These 29 Are the Standouts
Levi's 501s: a Hollywood go-to.
-
The Highly Specific Denim Trend Even I Didn't See Coming
Danielle Haim is a fan.