The Gen Z fashion icon continues to push boundaries with her sharp and ever-evolving sense of style.

When <a href="https://preview.lofficielusa.com/fashion/emma-chamberlain-style-fashion-louis-vuitton-cartier-virgil-abloh" target="_blank" rel="noopener">Emma Chamberlain</a> first skyrocketed to fame in 2017, she became known for her trendy, youthful fashion sense. Her signature look often featured a high ponytail adorned with a <a href="https://www.lofficielusa.com/fashion/oversized-scrunchie-summer-2024-hair-trend" target="_blank" rel="noopener">scrunchie</a>, paired with the iconic <a href="https://www.lofficielusa.com/fashion/shearling-sherpa-accessories-2021-teddy-trend" target="_blank" rel="noopener">teddy coat</a>&mdash;an item she popularized, sparking a wave of influence that led countless brands to stock their shelves with the cozy staple.
<a href="https://www.lofficielusa.com/fashion/louis-vuitton-emma-chamberlain-charli-damelio-lv-squad-lvsunset-shoes" target="_blank" rel="noopener">Chamberlain</a> embodied the ideal of what every teenage girl aspired to be. The internet closely followed her journey as she transitioned from YouTuber to podcaster, model, and businesswoman. As she matured into adulthood, her style evolved right alongside her. While <a href="https://www.lofficielusa.com/pop-culture/emma-chamberlain-christmas-holiday-fail-youtube" target="_blank" rel="noopener">Chamberlain</a> always had a keen sense of fashion, it wasn&rsquo;t until this past year that she made a bold shift, embracing more daring and experimental looks&mdash;and we&rsquo;ve loved every moment of her fashion transformation.
Working closely with almost every top designer in the game, such as <a href="https://preview.lofficielusa.com/fashion/nicolas-ghesquiere-best-handbag-designs-louis-vuitton-bags" target="_blank" rel="noopener">Louis Vuitton</a>, Jean Paul Gaultier, Maison Margiela, Thom Browne, and <a href="https://preview.lofficielusa.com/fashion/prada-unfpa-fashion-expressions-program-2024" target="_blank" rel="noopener">Prada</a>, to name just a few, Chamberlain has embraced a different approach to fashion and experimentation. Whether modeling in the show or watching from the sidelines, Chamberlain has yet to disappoint us in the fashion department.&nbsp;
In honor of <a href="https://www.lofficielusa.com/fashion/new-york-fashion-week-spring-2025-schedule-designers-shows-what-to-see-do-nyfw" target="_blank" rel="noopener">New York Fashion Week</a>, L'OFFICIEL has rounded up some of the fashion icon's most daring looks yet.&nbsp;

One of Emma Chamberlain's most recent daring looks comes from one of her favorites, <a href="https://www.lofficielusa.com/fashion/jean-paul-gaultier-le-beau-le-parfum-madonna-pop-culture-design-history" target="_blank" rel="noopener">Jean Paul Gaultier</a>. Wearing a shirt without really wearing the shirt, this avant-garde look is complemented with simple and sleek elements to keep attention on the main attraction of this outfit: the blouse.&nbsp;

For <a href="https://www.lofficielusa.com/fashion-week/thom-browne-fall-winter-2024-haute-couture-runway-show-review-images" target="_blank" rel="noopener">Thom Browne</a>, Chamberlain rocked a bold checkered suit jacket paired with a matching checkered mini skirt. She completed the daring look with knee-high tube socks and black heels, adding a playful edge to the ensemble.

For <a href="https://preview.lofficielusa.com/fashion-week/rick-owens-mens-spring-summer-2025-runway-show-review" target="_blank" rel="noopener">Rick Owens</a>, Chamberlain fully embraced her femininity, making a bold statement with this iconic underboob moment. This daring style is a departure from her usual looks, and she pulled it off effortlessly.

For <a href="https://preview.lofficielusa.com/fashion/prada-unfpa-fashion-expressions-program-2024" target="_blank" rel="noopener">Prada</a>, Chamberlain had the internet buzzing&mdash;both positively and negatively&mdash;with this bold look. While the outfit itself was striking, featuring a cinched blazer and a sheer mid-length skirt, it was her edgy micro bangs that really stole the spotlight and fueled the conversation.

Embracing the avant-garde essence of the iconic luxury brand <a href="https://preview.lofficielusa.com/fashion/zendaya-met-gala-2024" target="_blank" rel="noopener">Maison Margiela</a>, Chamberlain effortlessly aligned with the brand's aesthetic. Sporting an edgy hair and makeup look, she pushed boundaries by tucking her blouse into black tights, creating a striking and unconventional ensemble.

Another outfit by <a href="https://preview.lofficielusa.com/fashion/jean-paul-gaultier-iconic-looks-designs-cone-bra" target="_blank" rel="noopener">Jean Paul Gaultier</a>, Chamberlain wears a sheer black lace corset dress with intricate floral detailing, exuding both elegance and boldness. The strapless silhouette highlights her figure, while matching lace gloves and stockings elevate the look with added drama and cohesion. A sleek choker necklace, paired with oval sunglasses, injects a modern, edgy twist to the vintage-inspired aesthetic

Chamberlain's look is both simple and daring, created by a bold twist on classic layering. She pairs a bold red bra over a basic t-shirt, tucking it in for a playful yet edgy aesthetic. This unexpected combination brings a cool, fashion-forward vibe to an otherwise straightforward outfit.

In what may be her most daring look yet, Chamberlain tried out a different silhouette for none other than <a href="https://www.lofficielusa.com/fashion/andreas-kronthaler-vivienne-westwood-interview-art-activism-brand" target="_blank" rel="noopener">Vivienne Westwood</a>. Along with the bold shoulder silhouette, the makeup is intense and bold, with dark lipstick and dramatic eyes matching the gothic vibe of the outfit. The hair is styled in a sharp, sculptural manner, pointing upward in a spiky formation, adding to the avant-garde aesthetic

Emma Chamberlain wearing Jean Paul Gaultier. Getty Images.

Emma Chamberlain’s Boldest and Most Daring Fashion Moments

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