The Risk Taker of the Year has been an award I have handed out every year since I started If I Was A Stylist back in 2011, except for some reason when I skipped giving the award in 2013. I have awarded the title to Rihanna three times. It has also gone to FKA Twiigs, Zendaya, and Elizabeth Banks. This year I am taking a risk. Instead of opting for someone who pushed the boundaries with avant garde couture ensembles I have decided to give the award to a man for the first time. I knew there was going to be something about Timothee Chalamet when I first saw it almost two years ago at a photocall during the Berlin Film Festival. He didn’t disappoint during awards season wearing a lot of Berluti, but it was really his promo tour for his latest film Beautiful Boy this fall that really sealed this award for him. He rocked bold prints, cutouts, colors, and embroideries from Alexander McQueen, Haider Ackermann, Alexander McQueen, and Louis Vuitton on a lot of the red carpets this fall and each suit seemed to be more lust worthy (especially for me whose life motto is #WhenInDoubtBeExtra) and I am really excited to see what he will bring to awards season next year. He rocked suits with boots, t-shirts, and sneakers for occasions that you would typically expect to see full on tuxedos for. He pushes the boundaries of menswear and I am really excited to what more lies in store from the young actor.