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Turned Gentleman: Netflix Tiny Pretty Things' Damon Gillespie

The Quintessential Gentleman kicks off its digital fashion series, Turned Gentleman, spotlighting the new and next wave of cultural disruptors. This series features the rising talents of today who are impacting the world around us. A Turned Gentleman is confident, distinguish, and a rule breaker. We explore their stories through their lenses and learn of the inspirations that have molded them. From their communities and upbringings, they've embraced the culture that influenced their style.

Shirt: Dior | Accessories: Jimmy Crystal NY | Hat: Zara | Gloves: House Of Underwood | Pants: Mercy X Mankind

Damon Gillespie is making a name for himself in the world of television, currently starring on the Netflix show Tiny Pretty Things. As someone who grew up in the world of performing arts, Gillespie is not exactly new to show business. However, with his increased popularity and maturation into adulthood, he has grown in regard to his sense of personal style and fashion. The Quintessential Gentleman had a chance to speak with Damon about this transition, his role on Tiny Pretty Things and the impact he wishes to have on the culture.

How did you get your start in the entertainment industry and what drew you to your character, Caleb, on the show Tiny Pretty Things?

When it came to Caleb in “Tiny Pretty Things,” I wasn’t drawn to him until I got my first call back for the role. As a performer, I try not to get too attached to a role too soon and I’m of the mindset that when you audition, you give it all you have and then let the character go until you find out if you got the part or not. When they gave me the callback, I read the script and wanted to have some fun with the character, so I asked the showrunner if I could make him southern, which I was allowed to do. I have had fun playing the role and making it my own.

On Tiny Pretty Things you play a ballet dancer; what elements of your character reflect parts of your own life experience?

Caleb is a dancer, and I grew up dancing, although I did not dance ballet. I also went to a performing arts school, so I understand the dynamic of competition within respective majors.

We made the character from North Carolina, which is where my family is from and it was easy for me to understand what it’s like to grow up in a disciplined environment because all the men in my family were in the military. I also had to deal with a good amount of prejudice growing up, similar to my character on the show.

What was it like growing up in Chattanooga and how would you describe the culture there during the 1990s and early 2000s?

I think I had a different view of Chattanooga growing up than most people did. I moved around a lot, so I didn’t really understand Chattanooga until the mid-2000s. As I got older, I started to realize that Chattanooga is this incredible arts-supporting community with a lot of cultural activities like outdoor concerts and community theater; it is still one of my favorite places in the world.

Fur: Saks Fifth Avenue | Pants: Celine

When did you first discover fashion and how did it impact you?

I honestly wasn’t really into fashion growing up, but I have always loved the idea that someone can build things that we need and someone else can take those things and make something so incredibly complex and beautiful.

From a personal standpoint, I would say that the 90s had a large influence on my style because I was stuck in that decade for a while; my clothes were a little too big and everything kind of swallowed me until I went to college. During this time, I started to find different brands that made me feel good and also worked for my body type. I like to show off my body, so I like clothes that hug me, but that I can also move in.

What brands do you gravitate toward?

The brands I have found to be most conducive to my lifestyle are Kit and Ace and The Kooples, but of course, I always love a good pair of Nikes as well.

Jacket: Mercy X Mankind | Hat: Zara

If you could shop the closets of three celebrities who would they be?

I think Rami Malek always looks good. I like Jamie Foxx’s hat game. I think Kevin Hart and Dwayne Johnson do a good job of mixing sportswear with dressier clothes; I like that they bring elements of their own cultures to traditional menswear.

If you were having dinner at the White House with Vice President Kamala Harris, what do you think you would wear?

To feel my best, I would definitely wear a made-to-measure suit, probably in an olive-green color to bring out my eyes. I would pair it with a white shirt and a black tie with an Eldredge knot, something I wear for all the major events in my life. I would also add a nice watch and good pair of shoes to finish the look.

Jacket: Mercy X Mankind | Pants: Mercy X Mankind | Boots: Sunni Sunni | Hat: Zara

What characteristics should all gentlemen possess?

I grew up in the south, so chivalry is always important to be considered a gentleman, in my opinion. I also think that being a gentleman involves how you treat people and ultimately what you stand for.

Entertainers, through their characters, their lifestyles and their clothing have the opportunity to greatly impact larger society; what impact do you hope to have on young men of color as you progress in your career?

When people see or read about me, I want them to know that anything in the world is possible. I want people to know it is important to stand up for what you believe in and to know and defend your worth, but that you can accomplish this with kindness.

Shirt: Dior | Accessories: Jimmy Crystal NY | Hat: Zara | Gloves: House Of Underwood

Editorial Credits:

Photographer: Christian Hicks

Stylist: Monsieur Parie

Creative Director: BYoung Agency

Photo Assistant: Kudyba Sall

Digital Tech: Brando Wallace

Groomer: Christina Talmont


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Tonya Gillespie
Tonya Gillespie
Mar 09, 2021

Damon is amazing. Thank you for this.

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