Lilly Singh

On fashion, representation, and the Gold Gala


Talent: Lilly Singh @lilly

Photos: Simrah Farrukh @simrahfarrukh

Fashion: Benjamin Holtrop @benjaminholtrop

Fashion Assists: Emily K.E. Johnson @emilykejohnson, Rasheed @rasheedmkanbar

Makeup: Anton Khachaturian @antonmakeup

Hair: Kat Thompson @kattthompson

Known for her YouTube content, Lilly Singh has made a name for herself by combining her charisma and humor. Since the start of her career, Singh has added actor, producer, television host, comedian, and New York Times best seller author among her accomplishments. She also established Unicorn Island, a nonprofit dedicated to empowering underrepresented communities to tell their stories.

On Saturday, Singh got ready with Timid for her first ever Gold Gala. The annual event thrown by Gold House is perhaps the most anticipated night of the year for Asian, Native Hawaiian and Pacific creatives, companies, and communities. “I’m very, very excited!” Singh shared. “I love being in a room full of people who… share similar trauma in some ways. When I can bond with the guests at my table like ‘Your therapist and you talk about this too?!’—that’s always nice.”

She continued, “I just love the sense of community and connection. I think now, more than ever, it’s extremely important. I’m looking forward to meeting new faces that I’m a huge fan of, that I never met before, and just reconnecting with friends. Also seeing the FASHION. Yes, go off Asian fashion! We love it.”

Fashion has always been important to Singh, who has made waves with her androgynous outfits for her Diwali parties. “Fashion, first and foremost, is rebellion,” she stated. “It has always been that in my life. As someone who has always played with aesthetics leaning masculine as well as feminine, and colors—I’ve always felt like fashion is a great vehicle to express yourself outside of the box. Which is why I’ve always believed that fashion should not have rules. I really contend with the sentiments of ‘faux pas’ and ‘This is not in.’ Fashion should be someone’s expression in which they put something on and feel a certain way that is empowering for them. I plan to put on this look, feel like my absolute best self, and go absolutely crush my night tonight.”

The creatives behind her look for the event were fashion stylist Benjamin Holtrop, assisted by Emily K.E. Johnson and Rasheed, makeup artist Anton Khachutarian, and hair stylist Kat Thompson. Holtrop picked out a sleek, black feathered suit for her outfit from designer Le Thanh Hoa, and unique statement diamond earrings with matching rings from B.P. de Silva, Emilienne Chatelain, Jacquie Anderson, and Kasun completed the look. “We drew inspiration from her family’s culture and the symbol of a peacock,” Holtrop explained, “and we wanted the look to be a mix of masculinity and femininity.”

“I told Benjamin that the peacock is a major figure in my life as it is the national bird in India, and especially prominent in Punjabi culture. I wanted to feel like and have that same grandiose,” Singh recalled. “The look I’m wearing really gives peacock vibes. It’s very feathery on top with a structured and very extra silhouette. My jewelry accentuates these elements. The bold black with the contrasting glitz all lend to a peacock’s presence. You know when you see a peacock and everyone is losing their mind because it’s so extra and takes up space? That’s what we’re going for and that’s how I feel!”

Also leaning into the theme, Thompson said, “We were leaning into the peacock feel and taking each part of glam one step further. I was inspired by the shape of Lilly’s coat and the movement of the feathers. Because the sleeves or the jacket were so sculpted, I wanted her hair off her neck to really showcase the details. I added a fishtail braid bun to create more detail in her hair, and left out small pieces of hair in the front to mirror the movement of the feathers.“


For makeup, Khachaturian went for a smokey-eyed look to complement her hairstyle. “We really wanted to give a sultry and glamorous vibe,” he said. “She can literally pull off any makeup look, so we knew we had to go bold with it for tonight’s event…and wardrobe!”

As the creative team put together the finishing touches, Singh mused on theme for this year’s gala—A Gold New World. “The conversation of representation has been so hot over the past few years,” she said. “But to be honest… Some days I feel like we’re making great progress and other days I feel like this industry is taking steps backwards. The way we view representation can often be one-dimensional, focusing on how many people on screen are of ‘this’ or ‘that’ community or subculture.

“It comes to the decision makers—the people that decide what ‘broad’ means, what is ‘relatable,’ and what will be ‘buzzy’—those rooms need to become truly diversified at every level, but especially at the executive level, and that’s when we’ll really benefit. That’s the tomorrow I’d imagine for us, built by all of us. One that is us on screen and firmly embedded in the business across every decision-making room and role.”