It was the emergence of boy bands that stirred Ben Sharkey’s fantasies of becoming a singer. He knew he could sing, but he didn’t have access to training while growing up in the tiny village of Stockbridge, southeast of Lansing. It wasn’t until he transferred to Ann Arbor Pioneer High School that he started to understand what his voice could do: The music teacher tested his range and found he could reach from the lowest baritone to the highest alto of anyone in the class.
When he knocked over a stack of a roommate’s CDs while cleaning his then-boyfriend’s apartment, a Harry Connick Jr. CD popped out. Listening to that CD, he was hooked. “I was obsessed with his style and the big-band arrangements and the energy in his voice,” he says. “I could match every note he could sing.”
In 2007, during his years at the College for Creative Studies, he jumped on board the YouTube singing trend and was soon on the front page. Though his popularity grew fast (he has over 5 million views worldwide for more than 70 clips), “the negativity on those kinds of platforms with comments … just really turned me off,” he says. Instead, he focused on live performances; one of his favorites was opening for Robin Thicke at the Royal Oak Music Theatre.
Sharkey’s working on a new recording of jazz standards to go with his 12-piece oil-on-canvas photorealistic art series called The Disappearance of the Gentlemen, which the Detroit resident says reflects our culture and is “an advertisement for the aesthetic of the gentleman.” The suited subject in each painting has no head so “anyone can look at the suit and picture themselves in it.”
My go-to look for daytime is …
A T-shirt and jeans with a James Dean kind of vibe. I might wear some leather boots or white sneakers with it, just kind of classic. Or an old café racer leather jacket.
When I want to pump up my look, I …
Throw on a fedora or a newsie, pants that have a nice pattern, stripes, or some kind of flair to them. For nighttime, maybe something a little shimmery.
The colors in my wardrobe:
I like to wear darker things in the winter — blacks and browns and dark blues. In the spring, lots of floral colors. Even bright oranges in the fall.
What’s most important in suiting is …
The structure of the suit. And the lines. The quality of the suit is very important. I’m a big fan of wide lapels. They make my heart beat out of my chest. [I accessorize with] a lapel pin and definitely a pocket square. You have to have one or the other. It looks like you’re a used-car salesman if you don’t have some flair.
A trend I stay away from is …
Wearing the upscale sweatpants. I just don’t like it. It’s still sweats to me.
My favorite item in my closet is …
My Henry Ford limited-edition pocket watch. I also have a sequined double-breasted black suit that I got from Dolce Moda [in Birmingham]. That’s one of my favorites to wear.
I’m most inspired by …
Tom Ford. I love anything that Tom Ford touches. He’s just got it down.
My favorite places to shop are …
Dolce Moda. Saks Fifth Avenue. I like Greyson downtown.
My advice to young musicians trying to create a signature look:
Be bold and don’t be afraid of the critics.
This story originally appeared in the June 2025 issue of Hour Detroit magazine. To read more, pick up a copy of Hour Detroit at a local retail outlet. Click here to get our digital edition.
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