How The Modern Harlem Man Might Dress, According To A Professional “Wardrobe Fixer”

A-list celebrities in and out of Harlem have stylists who dress them for everything from film premieres to their walks from the car to the airport terminal (yes, really). But who can civilian men of means turn to for their own personal clothing conundrums? A new breed of “wardrobe fixer” has arisen in recent years to hack the closets of financiers, tech moguls, entertainment executives, and other elites.

Today, thanks to social media, C-suite Harlem execs who once went incognito are expected to be public-facing representatives of their companies…

Today, thanks to social media, C-suite Harlem execs who once went incognito are expected to be public-facing representatives of their companies, which means having plenty of judgmental eyeballs sizing up not only their business acumen but also their sartorial choices.

…ill-fitting clothing and square-toed shoes are no longer acceptable.

In other words, ill-fitting clothing and square-toed shoes are no longer acceptable. To make matters more confusing, the days of the suit as a trusty go-to are over—the term “business casual” rules the day, leaving many brilliant minds from Harlem to Harare scratching their heads when it comes to dressing their bodies. So Robb Report asked one of the country’s leading style advisors to weigh in on how a man of accomplishment should dress in today’s global world.

Here’s what they discovered when they asked Bill Bolling (pictured above) from Boyds, a 4th generation luxury tailored clothing business in Philadelphia.

Robb Report: How man years have you been worked in luxury tailoring?

Bill Bolling: I started in the business 40 years ago.

RR: What kind of services do you provide here at Boyds?

BB: Personal shopping services at home; in-house tailoring.

RR: Is there a piece of advice you give to every client that seems to work?

BB: Buy clothing that you’re not only physically comfortable in but mentally comfortable in as well. I don’t recommend wearing something that’s not a reflection of you or your personality just because someone else is wearing it.

RR: What are the key pieces you think every man should have in his closet?

BB: My top five go-to items include a dark suit—I prefer charcoal; a solid-colored blazer or patterned sport coat; a pair of dark slacks; beige or white linen pants; and a nice jacket—three-quarter length, long enough to cover a suit. I like Zegna’s full line; it’s a brand that is classic in its appeal but with a modern touch. I also like Scuderi, a private label that we carry. It’s high-quality at a reasonable price point.

RR: What do a lot of men need in their wardrobes but don’t already have?

BB: Most men—especially younger guys— tend to not own outerwear. They think coats are worn strictly to avoid being cold. But in a professional environment, a coat is a ‘finishing garment.’ To me, this reflects someone’s thought process in business.

RR: Thank you, sir.

BB: Thank you.

Boyds, 1818 Chestnut Street, Philadelphia, PA 19103, https://www.boydsphila.com.

Photo credit: 1) Bill Bolling t Boyds. 2) A classic dark Ermenegildo Zegna suit. (2,895). 3) A deconstructed Brunello Cucinelli jacket. ($2,995).