From “fashion don’ts” to must-haves: how stars are turning quirky, comfy, and unconventional styles into today’s trendiest statements.
In recent years, the fashion industry has seen a surprising twist—ugly fashion, once deemed unworthy of the runway, is now gracing red carpets, high-fashion campaigns, and street-style looks. Celebrities are leading the charge in bringing seemingly unfashionable trends like cargo pants and Crocs back into the limelight, proving that in today’s world of fashion, anything can be cool with the right attitude. What was once considered "ugly" has found a fresh appeal, becoming a symbol of individuality, comfort, and a newfound approach to personal style.
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Cargo pants, long relegated to the world of utilitarian workwear or 2000s fashion disasters, have made a comeback in a major way, thanks to the likes of Bella Hadid, Kendall Jenner, and other style icons. These pants, originally designed for military personnel and later adopted by the hip-hop community, are now a staple in celebrity street style. Once seen as baggy and unflattering, today’s cargo pants are reimagined with sleek, tailored cuts, high-waisted designs, and fun, exaggerated pockets, adding an edge of urban cool to everyday wear.
Bella Hadid, for example, has been spotted in oversized cargo pants paired with stylish crop tops and trendy sneakers, creating an effortlessly chic vibe. Her ability to elevate the once-dismissed trend has made cargo pants a must-have for fashion-forward individuals who want to embrace comfort without sacrificing style. In many ways, these revamped cargo pants represent a departure from the traditional body-con styles that dominated the early 2010s, embracing a looser, more laid-back fit that prioritizes functionality without compromising on fashion.
Kendall Jenner, known for her minimalist yet impactful fashion choices, has also been photographed in various cargo styles, showcasing how the item can easily transition from casual streetwear to high-fashion appeal. Whether she pairs them with a simple white tee or a luxe leather jacket, Jenner proves that cargos can be just as chic as any high-end designer trouser.
When it comes to "ugly" fashion, few items have sparked more debate than Crocs. The rubber slip-ons, originally designed for comfort and practicality, were once reserved for gardening or hospital workers. However, in recent years, they have morphed from a questionable footwear choice into a fashion statement, especially within the celebrity community.
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Crocs’ rise to fashion fame can be attributed to stars like Justin Bieber, who has been a vocal advocate for the brand, and fashion icons like Post Malone, who partnered with the brand to release his own line of Crocs. These collaborations have brought the shoe into the mainstream, turning it from a meme-worthy punchline into a fashion-forward staple. The brand's success lies in its ability to blend functionality with a playful edge, often incorporating bold colors, custom Jibbitz charms, and even high-fashion elements into the design.
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Post Malone’s Crocs collaborations are particularly noteworthy, with limited-edition designs quickly selling out, often featuring funky designs and bold patterns that have redefined the shoe’s "ugly" image. These custom Crocs have become a symbol of anti-fashion, showing that high fashion doesn’t always need to adhere to traditional beauty standards. The trend’s acceptance by stars like these proves that style today is more about expressing personality and comfort than adhering to rigid aesthetic norms.
The rise of "ugly" fashion isn’t just about embracing a specific trend—it's about challenging the very notion of what is considered beautiful or stylish. Celebrities are embracing the chaos of mismatched outfits, exaggerated silhouettes, and unconventional textures, resulting in a new wave of anti-fashion. This trend rejects the polished, picture-perfect looks of the past in favor of eccentric, raw, and sometimes chaotic styling choices that speak to individuality and creative freedom.
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Stars like Billie Eilish and Harry Styles have become poster children for this anti-fashion movement, showcasing bold, unconventional styles that mix and match genres, textures, and colors. Eilish, known for her oversized clothing and nonchalant approach to fashion, regularly sports outfits that challenge traditional beauty standards. Her boxy, often mismatched outfits send the message that being "cool" is about comfort, confidence, and embracing one's personal style, rather than adhering to any specific rules of fashion.
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Harry Styles, with his gender-fluid wardrobe and flair for mixing masculinity and femininity, has also become an icon of this new wave of fashion chaos. His bold choices—like wearing a feather boa to a red carpet event or pairing a floral dress with loafers—show that style today is about breaking free from outdated norms and making choices that feel authentic, not dictated by anyone else’s opinion.
When high-profile celebrities endorse "ugly" fashion, it immediately gains credibility and visibility. It’s no longer seen as a fashion faux pas but as a statement of personality, individuality, and even rebellion. Celebrities have the power to influence mass consumer trends, and with social media platforms amplifying their choices, "ugly" fashion is no longer confined to the fringes. What once seemed unpolished and unconventional has now entered the realm of fashion-forward, thanks to the stamp of approval from A-list stars.
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For instance, rapper Kanye West’s "Yeezy" line has made waves by embracing minimalism and an almost utilitarian aesthetic. His bulky sneakers and oversized clothing, while not immediately considered stylish by traditional standards, have influenced a generation of fashion enthusiasts to rethink what is considered "cool." The oversized and often baggy designs, paired with unconventional footwear, have set a precedent for a more relaxed approach to luxury fashion.
Similarly, the influence of Instagram and TikTok has allowed "ugly" fashion to flourish in the mainstream. Fashion influencers, many of whom are inspired by celebrity street style, are showcasing these "imperfect" looks to their millions of followers, proving that style today isn’t about fitting into a mold but about celebrating personal expression.
In 2025, fashion is about breaking free from traditional norms and embracing individuality. What was once deemed "ugly" is now embraced as a form of self-expression, comfort, and creativity. Celebrities like Bella Hadid, Kendall Jenner, Billie Eilish, and Harry Styles are reshaping the conversation around what is stylish, making "ugly" fashion cool again.
From the resurgence of cargo pants to the popularity of Crocs and beyond, it’s clear that the boundaries of what’s considered fashionable are being redefined. In this new era, anything can be stylish if you wear it with confidence.