The Iconic Fashion Candids: Analyzing the Influence of Celebrity Street Style
- Ella Henry-Schaeffer
- 2 days ago
- 6 min read
What do icons such as David Bowie, A$AP Rocky, Rihanna, Bella Hadid, and Princess Diana all have in common? The answer is quite simple. Each of these celebrities, along with so many others, have paved the way in fashion with each authentic outfit and every candid photo taken of them on the street. Their contribution to the fashion industry stems from their everyday clothing and snapshots of their most highlighted looks. “Off-duty” dressing is oftentimes more of a statement than the outfits we see in performances or on the red carpet. From androgyny to the revival of vintage pieces, these public figures influence the fashion we know today.
What is Street Style?
In the simplest terms, celebrity street style refers to the outfits famous figures wear when walking from one place to another. Since the dawn of celebrity culture, the paparazzi have captured candid photos of celebrities in their day-to-day lives, documenting their personal style. Street-style photography heavily contributes to style inspiration for many individuals. Have you ever seen one of these photos and thought, “Wow, I’m going to need to buy a fur coat like that!” That’s because the majority of clothing trends today have originated from celebrity street style. These photos go viral, and all of a sudden, everyone you know has something very similar. This pattern has been circulating for decades. Numerous artists, actors, actresses, and models have earned the additional title of “Fashion Icon” through their street style looks. By taking a look at the top fashion icons over the past few decades, you’ll recognize the significant impact they have on what’s trending and popular today.
The Glamour of Breaking Gender Norms
Male artists like David Bowie and A$AP Rocky have blended masculine and feminine stereotypes in clothing throughout their careers, becoming pivotal figures when it comes to androgyny in fashion. Because of their androgynous everyday looks seen in spontaneous photos, the lines have been drastically blurred. Their sense of self-expression is seen through garments that are traditionally considered “feminine."
David Bowie
One of the most influential artists in so many aspects of his career, David Bowie, is considered one of the most bold and flamboyant rock musicians of the ‘70s. He’s changed the trajectory of typical everyday male rock stars, from jeans and a t-shirt to tailored coats and innovative color choices. Bowie challenged numerous gender stereotypes when it came to his wardrobe and the makeup he experimented with. As Wesley Morris wrote in his 2013 New York Times essay, “The Man Who Remade the Man: On David Bowie and His Enduring Influence on Fashion,” Bowie possessed a unique quality: “Men would find inspiration in his sartorial spirit, in his fearless readiness to try anything, to use clothing replete with reference as a means to say something.” Bowie carried himself with confidence, swag, glamour, and, of course, his staple extravagant suits.
While his concert costuming was quite groundbreaking, his everyday wear was also very impactful. Bowie’s distinctive androgynous stylistic choice was in the tailoring of his clothing. High collars, tightly-cut suits, and garments made with traditionally feminine tailoring techniques.
A$AP Rocky
The one and only “Fashion Killa,” A$AP Rocky, has become one of the most influential rappers in the fashion world. Rocky is known for his feminine accessories, painted nails, and his blending of luxury menswear with streetwear. With the use of layering and gender-fluid silhouettes, he’s garnered lots of attention over the years. His personal style is highly controversial as it goes against the typical and expected attire that many rappers usually follow. Rocky’s looks have gone far beyond crossing gender norms. His outfits are evolutionary, creative, and have changed the way we look at everyday fashion. These outfits consist of pieces that seem to have been thrown together by random selection, yet always seem to come together as a piece of art.
A$AP Rocky’s style is more than just his contribution to trends; it’s highly recognized in the fashion industry. The Council of Fashion Designers of America (CFDA) honored A$AP Rocky with the Fashion Icon Award in 2025, declaring his status as one of the most culturally impactful figures in contemporary style. He’s earned the title of “music’s best-dressed man” from W Magazine and has consistently appeared high in rankings on Complex’s annual Best-Dressed Rappers lists.
By embracing the clash of feminine and masculine clothing, these male celebrities all had an impact on not only the normalization but popularization of wearing articles of clothing that were typically considered only for a specific gender.
The Woman Behind Luxury Streetwear: Rihanna
Otherwise known as a global superstar and one of the best-selling music artists of all time, Rihanna is also famous for combining couture and casual wear. She incorporates straight-off-the-runway pieces with something simple, like a pair of baggy jeans. This has become her staple look over the years, breaking the barrier between designer and ordinary garments. She’s been photographed in oversized blazers, vintage t-shirts, and baggy jeans. All pieces that have gone viral and been trending since her appearance. Along with the other celebrities highlighted, Rihanna walks with confidence. Her street style candids are iconic not only because of the outfit she has on but because of the way she wears it.
While delivering a speech at the 2014 CFDA Awards, Rihanna described her attitude towards developing her own unique style: “I grew up on a really small Island, and I didn’t have a lot of access to fashion, but as far as I could remember, fashion has always been my defense mechanism. Even as a child, I remember thinking, she can beat me, but she cannot beat my outfit.”
According to Marie Claire, “what makes Rihanna a style icon is the fact that she doesn't wait for galas or award shows to take fashion risks—her street style is just as enviable and impressive. A fashion chameleon, Rihanna isn't afraid to experiment, and loves to take pieces straight off the runway and mix them up to make the look her own.”
Bella Hadid and the Comeback of Vintage and Y2K
The early 2000s era has finally come back around with the help of supermodel Bella Hadid and her well-known “model-off-duty” looks. Her outfits reflect many aspects of the Y2K style, making her one of the biggest influences of the vintage clothing revival. According to Bustle, “Bella Hadid is singlehandedly keeping the early 2000s fervor alive.” Bella Hadid has stated many times that she often shops on Depop, an app for people to buy and sell new, used, and vintage clothing. She’s been seen wearing a large range of vintage designer pieces, from dresses to fur coats to low-rise jeans. Her staple accessories are thin-framed, retro sunglasses and statement handbags.
Bella Hadid is unique amongst most celebrities in the way that her audience consists mainly of a younger generation. Many teens and women in their early 20s look up to her and view her as the epitome of their style inspiration. She is considered one of the most influential fashion icons of our time, not just because of her supermodel status, but also because of her everyday looks.
Princess Diana’s Popularization of Chic Athleisure
Princess Diana was an innovator of the "athleisure look.” Her iconic oversized crewneck sweatshirt and biker shorts outfit will be a staple in fashion for the rest of time. Not only has this look made its way to everyday people, but it has influenced many modern celebrities in their own personal style.
In August 2019, Hailey Bieber did a Princess Diana photoshoot for Vogue Paris, which paid tribute to this iconic look. Princess Diana solidified the idea that you can be comfy all while looking stylish at the same time. Her paparazzi photos went viral and influenced many fashion trends that are still relevant today.
Fashion trends will continue to be influenced by celebrity street style and the casual, candid photos we see going viral every day. Although it’s important to note, not just anyone can be considered a “fashion icon.” These celebrities have solidified their title with innovative ideas, each creating their own personal style. They’ve made it clear that the best outfits come from their truest self. Everyone featured uses fashion as a form of self-expression. They wear the clothes, not the other way around. And that’s the real hallmark of a fashion icon: authenticity.
Written by: Ella Henry-Schaeffer
Edited by: Graeme Duffey
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