It began, as is so often the case, with a stylish mom. Born and raised in Milwaukee, Wisconsin, stylist Willie Sinclair III credits his mother's '90s fashion as the first stop on a journey which has led him to styling one of television's most chaotically delicious personalities: Wendy Williams. "She was a super stylish teacher and would get all dressed up for work before I went to school — I'm talking blouses with shoulder pads, matching headbands and a full face of makeup. It was amazing to watch her glam process over the years."
After graduating from the Fashion Institute of Technology in 2013, Sinclair III began a design apprenticeship as a way to buy time in order to figure out how best to break into the industry. "It was an opportunity to make a bit of money because moving back to Wisconsin was not an option." He knew he didn't want to be a designer, so it was a matter of finding a path both viable and desirable. And then came Ms. Wendy.
"Thank you for noticing!" Sinclair III beams when I pay necessary mind to the Christopher John Rogers look worn by Williams on the Season 12 premiere of her eponymous chat show. "I am a pop culture connoisseur and I do my research; nothing is without intention. When new brands and looks cross my radar, I take note and add images to my moodboard to stay inspired. I want viewers to be curious about what Wendy will wear next," he says. This season, Sinclair is focused on incorporating a fresh crop of design talent into the repertoire which has included, in addition to CJR, Marine Serre, ALIÉTTE, Proenza Schouler, Preen by Thornton Bregazzi and Tibi for S12.
Below, we chat with Sinclair III about Wendy's style evolution, prioritizing Black designers and why certain fashion publicists won't loan to him for the show.
How did the Wendy gig come about?
My Wendy experience began in August 2012 when I moved to New York City and began interning in the wardrobe department at the show while attending FIT. At the time, I was the only intern at the show who knew how to sew. Therefore, I was given the task of custom sewing Wendy's bras to fit. One day I ran into her while waiting for the elevator and she called me her "sewing elf." The name stuck. About four months after my internship ended, I was invited to interview for the position of Wardrobe Assistant (replacing my former supervisor). I got the job and held the position for five years before being promoted to Wardrobe Stylist in 2018.
What was your perception of Wendy's style before you came on the scene?
Before joining the show I felt that Wendy's style could be characterized as very "Jersey." More is more, if you know what I mean. Lots of satin dresses, chunky jewelry and leopard prints. I joined the team as an assistant during a different era for the show and the fashion reflected that. We slowly shifted her style to fit a more traditional classic daytime talk show host aesthetic. She was wearing a lot of cashmere cardigans, Diane Von Furstenberg wrap dresses and pencil skirts. Looking back it was an important transitional moment in her style development and she looked great, but it felt a bit formulaic to me.
Besides bust, what are some key considerations when it comes to styling Ms. Wendy?
Since I began styling Wendy in September 2018, I've been intentional about incorporating Black designers into her wardrobe. Black designers have made undeniable contributions to the fashion industry and have historically been vanguards for global culture. Even so, their work is underrepresented on daytime television. Wendy's looks provide important commentary on the fashion landscape of daytime talk. It's important to normalize featuring Black designs for the sake of television history. In fact, in my very first week styling her, we did a casual Friday look featuring the "Stop Calling 911 on the Culture" T-shirt from Pyer Moss. In February 2020 we dressed Wendy in all Black designers in honor of Black History Month. We featured pieces from celebrated designers including Dapper Dan, Cross Colours, Stella Jean, Victor Glemaud, Laquan Smith, Hanifa and a viral look from Telfar. Besides that, I take into consideration how things will translate on television. I don't put Wendy into garments with small stripes or tiny polka dots because of the moiré effect.
"I've been intentional about incorporating Black designers into her wardrobe. Black designers have made undeniable contributions to the fashion industry... Even so, their work is underrepresented on daytime television."
How much of a say does Wendy have in what she wears?
Wendy is a very opinionated woman, so she has a lot of say in what she wears. The entire glam squad (Merrell Hollis on makeup and Jasmine Kelly on hair) meets with Wendy weekly to discuss what we're cooking up for the week ahead. It's her chance to say "Um... I'm not too sure about that dress" or "Maybe we should try that in a different color." This helps me keep the essence of her personality in every look.
How does COVID affect what you are able to pull?
While the pandemic has impacted my work in a number of ways, it hasn't really affected what I'm able to pull, because a lot of PR companies do not loan to our show. Black stylists have always had a difficult time being able to pull looks, especially when their clients are Black. Would I love for fashion publicists to loan to us? Of course! But the reality is that my assistant Chanel Smith and I have been forced to be exceedingly resourceful and creative in order to source items for Wendy to wear. All of the rejection letters, unanswered emails and "sorry we don't have any samples available" auto-responses from fashion and brand publicists have deepened our appreciation for the brands that do work with us. The challenges we face are indicative of a more deeply entrenched problem in the fashion industry around equity and inclusion, specifically as it relates to race. As brands and companies embark on their post-June 2020 journeys to develop anti-racist policies, I hope that a key part of their inclusion strategy is to ensure that their designs are seen on diverse bodies; this should include a range of complexions, sizes, genders, abilities, and so on.
"Black stylists have always had a difficult time being able to pull looks especially when their clients are Black. Would I love for fashion publicists to loan to us? Of course! But the reality is that my assistant Chanel Smith and I have been forced to be exceedingly resourceful and creative in order to source items for Wendy to wear."
Do you have a dream client to style?
This is such a tough question! I would have so much fun styling a music artist because of the versatility of their work. Styling a client across mediums — for music videos, live performances, photoshoots, and red carpets — would be a welcome challenge. Also, I think my work shows how much I enjoy the daytime television space, so costume design for scripted television and movies would also be a good fit for me.
Anything else I should know pertinent to knowing about you and what you stand for creatively?
I love a reference as much as I love embracing new talent. As a Black man, I understand the impact of controlling narratives and the importance of authentic storytelling. My core values as a stylist reflect my attention to what stories are shared, how they're told and who tells them. I hope those ethical commitments are reflected in everything associated with Willie Sinclair III. I am passionate about creating and am so excited to share more.
Welcome to "Wear Me Out," a column by pop culture fiend Evan Ross Katz that takes a look at the week in celebrity dressing. From award shows and movie premieres to grocery store runs, he'll keep you up to date on what your favorite celebs have recently worn to the biggest and most inconsequential events.
Header image: Reynolds Fernandez