He started off studying business management because of his mom, but really wanted to go to the Parsons School of Design in New York.
A stint working as a model, which included a shoot with photographer Annie Leibovitz, sparked his passion for the creative process.
While working in retail for Donna Karan, he phoned a friend who was running the Berliner fashion magazine and secured the fashion editor position.
He was consulting for French fashion magazine L’Officiel when asked to work on its 90th anniversary cover.
His only proviso was that a woman of colour be on the cover — in its 90-year history, the magazine had only featured two women of colour on its cover.
He put Beyoncé on the cover in a shoot honouring all the queens of Africa.
“It was a huge success, but also controversial because in one shot I darkened her face, paying homage to the Mauritanian queens, which is their tradition, but some people thought it was blackface,” said Tailly.
“I was so proud because the same cover was on all 48 editions across the world.
“I thought ‘Holy s**t’ when her mom phoned [and said they wanted me] to be [her] creative director!” he said.
The collaboration lasted three years, after which Tailly decided to start freelancing.
Speaking about the underrepresentation of black beauty in the media, Tailly said: “Seeing [actress] Lupita [Nyong’o] on the cover of Essence told women you are beautiful in your own way and style. I think there is beauty in everyone, fashion gives you a chance to show it.”
He tells how he met African Fashion International chairwoman Dr Precious Moloi-Motsepe in Paris at the Dior show.
“Everyone was delighted with her. She represents your country really well.”
Asked how he began working with Kardashian, Tailly said her husband, rapper Kanye West, had set it up.
While he was working with Beyoncé, Kanye was collaborating with the singer’s husband, music mogul JayZ. Kanye wanted Tailly to meet his wife.
“When I met her I thought: ‘Wow, what an amazing woman.’ Extremely nice, very well-spoken, exactly the opposite of [public] perception.
Asked how he gets to know and understand his clients, Tailly has one word: breakfast.
“Fashion can change the way we are. For me, fashion is not about clothes, it is about dreams, hope, acceptance and love. It has the power to make us feel good about ourselves.”