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Turning the Tables: Interviewing Osama Chabbi


Sharp, witty, and armoured with a multicultural sense of humour, confidence is his currency as he navigates the vast world of fashion. Recognized by Vogue Business as one of its 100 hand-picked next-generation entrepreneurs and agitators, his opinions are heard and respected by thousands of international followers, including the most influential industry insiders. Osama Chabbi is a fashion stylist, journalist and fashion commentator who has managed to turn his well-educated fashion reviews into an acknowledged and hard-to-earn seal of approval.

Photography: Zanki  Photography Assistant: Ramez Boctor

Chabbi did not have to contend with his parents when choosing fashion as a career. “My parents took it well,” he tells us. “Initially, my parents wanted me to go into fine arts because when I was younger, I was a very creative child who drew a lot. But realistically, I did not have the creative genius to become an artist. I would’ve known if I was a Picasso,” he laughs. “Designing did not interest me, but I knew I wanted to be in fashion. So I studied geopolitics but always said my end goal is fashion. I began as a stylist, freelancing for two years, and I think when I received my first pay cheque, my parents were reassured”.

The Tunisian by blood and French by upbringing critic first gained fame when he started posting his sincere thoughts about the latest fashion shows on his Instagram account – inadvertently joining a new wave of content creators who were changing the way fashion was digested and consumed. “During covid, fashion weeks were cancelled, and a lot of the regular shows were streamed live. I was attending all of them. I was watching the shows live, there were no guests, and it was a bit sad, but I came to the realization that the whole world was front row. We were all in the same seat. That was when I had an epiphany.” Osa continues with animated enthusiasm “I was like it makes no difference that I am at the show or not because the Vogue editor that I look up to that usually has something that I want – which is access to a seat at the show – does not have it right now because we are all at the same kind of seat. And that was when I realized that, well, people can take away people’s access, but essentially what we are all left with is our opinion,” shares Osama with a calm smile from his living room in Dubai.

Photography: Zanki  Photography Assistant: Ramez Boctor

After cementing his witty and well-informed Osa Reviews, his newest chapter promises heart-to-heart conversations with the who’s who of the fashion industry. From Haider Ackermann to Kris Van Assche, Casey Cadwallader, Amina Muaddi, Michele Lamy and Glenn Martens – the past few months have seen Osama take a serious leap of faith. Leaving his 9 to 5 job as a fashion stylist at Farfetch and taking his social-media friendly fashion reviews one step further. “I have not planned on launching an interview format at all. The idea has always been at the back of my mind, but the ‘how do you get access to these people’ was bigger than my dream.” Tweeting in November last year that his dream was to interview Haider Ackermann, the newly unshackled by a full-time job Osama, rapidly found himself in a room facing his dream after his 280 characters travelled far and wide until they reached Ackermann himself. “That was my first ever interview. It was my first time to organize production. I have never been on camera before, whether interviewing someone or even being interviewed.” His smile grows wider as he continues “something I will never forget is that when we were starting the interview, he was reading through my questions at the makeup room. And he was like, I actually have not asked you, what do you do for a living? And I said I think after this interview, I am a journalist.”

Landing his star-studded lineup of guests through DM exchanges and a lot of manifestation, the format remains loyal to his early-on vision. According to Osama, the interviews are intentionally democratic in terms of the choice of questions and frame. “There is a part of me that lacks an institutional fashion figure that is Arab. So, I cannot help but keep it institutional in the sense that it is a long conversation. It is not like all jokes instead it is a serious conversation.” Osama explains about his process to turn dialogues he only dreamt of into a reality watched by thousands “I love to sit with the people that have shaped and are shaping today what fashion is to me, consciously and subconsciously.”

Photography: Zanki  Photography Assistant: Ramez Boctor

As he names Azzedine Alaïa as his ultimate dream guest without a moment of hesitation, Osama already has his eyes set on his– likely more attainable – second in line dream guest, Victoria Beckham. “There is something about her that fascinates me. The fact that she was a pop culture character that was once perceived as a little bit of a tacky Spice Girl and I find it so impressive how she managed to navigate that and then got both feet in the fashion space with so much confidence. I just like what she represents as a woman. I like her presence. I find it very powerful.”

Chabbi’s journey exemplifies the fusion of passion and perseverance in the ever-evolving realm of fashion. For an individual to make waves in such competitive industry with its numerous forms and figures, you know there is unmistakable talent. From humble beginnings to international acclaim, Chabbi’s trajectory is a reminder of the transformative power of embracing one’s authentic voice. It highlights the other side of the journey of those who dare to dream and defy convention, suggesting that the true essence of fashion lies in the courage to be oneself.