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

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(Image credit: AKM/GSI)

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

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(Image credit: Getty Images)

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

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(Image credit: AKM/GSI)

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

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(Image credit: AKM/GSI)

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

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(Image credit: AKM/GSI)

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

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(Image credit: Getty Images)

Celebs like Gigi Hadid are never scared to go for the monochromatic look—even with their denim outfits like this blue skinny jean 'fit.

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Next, check out more skinny jean styling mistakes celebrities make.

Bobby Schuessler
Market Director

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent over seven 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 retialers 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. He has also worked across a variety of other media brands and fashion retailers like Refinery29, PureWow, Men's Health, and Gilt covering commerce, trend reporting, women's and men's fashion, home, and lifestyle.