Meet the Vintage Menswear Aficionado Who Can Teach You How to Nail Your Personal Style

Courtney Lichterman
·4 min read

What modern style aficionado hasn’t admired the graceful curves of a 1920s spectator shoe or the ramrod-straight shoulders of a 1940s dinner jacket and lamented that their generation had sartorially missed out? Instead of bemoaning that fact, musician, event producer and self-described “style activist,” Dandy Wellington has decided to make the past come to him, dressing exclusively in vintage clothing, whether at the dancehall or the dentist.

Born and raised in Harlem, this NYU Tisch School of the Arts alumnus counts Duke Ellington, Fred Astaire and Langston Hughes among his inspirations. Not surprising given that Wellington himself is a band leader, a dancer and—as anyone who has ever heard him speak about fashion knows—a true poet.

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The grandson of a tailor, he says that although he was always interested in fashion, it was a college friend who introduced him to the vintage community. “She was like, ‘You need to come with me because there’s a magical world where people love old things!’” Wellington describes his entrée into the vintage life as an “awakening” but is quick to explain that he espouses only the aesthetics of the past, not its ideals. “Vintage style, not vintage values” is his personal mantra.

Dandy Wellington photographed by Rose Callahan in NYC on Aug 30, 2012
Dandy Wellington photographed by Rose Callahan in NYC on Aug 30, 2012

When the pandemic hit and the performance side of his life was shut down, Wellington knew he had to switch gears and started a series of wardrobe building classes which include courses such as “Shopping Strategically,” and electives like “Mixing Colors and Patterns.” He also starting posting regular videos on his burgeoning YouTube channel, breaking down everything from how to tie a real bow tie to how to switch out a vintage wardrobe from one season to another.

He says his goal is not to see the streets of the world overrun with people who dress as he does, but to express their own personal style using vintage wear as the conduit: “I want to empower as many people as possible to see themselves the way they want.” And as vintage menswear’s popularity continues to grow among guys of all stripes, Wellington’s ethos is particularly relevant.

We asked him for a few pointers about how to get started in the vintage world.

Dandy Wellington
Dandy Wellington

What is your number one piece of advice for a man who wants to build a vintage clothing collection?

When asked a question like this most don’t want the truth, but for you, the Robb Report reader, I can thoroughly divulge. Building a vintage collection requires three key elements: the first is an understanding of history. After all, “vintage” is the study and appreciation of history through specific objects. This is best achieved by finding inspiration and doing historical research. Those who lived in the past possessed a life’s worth of things, thus there is a vintage enthusiast for everything from kitchen appliances to cars. Pull on the threads of what interests you and see where it leads.

Second is a deep love or intense appreciation for old things. To get caught up in the nuanced designs, intricate details and various trends of vintage items, one has to have a passion for it.

Finally, patience is a must. This is not a one-stop shop endeavor. Buying vintage takes an immense amount of time and patience. From going to estate sales to frequenting online vendors, the successful vintage collector immerses themselves in the hunt because the resulting quality is worth the wait.

Dandy Wellington
Dandy Wellington

What’s a good category to start collecting vintage?

The truth is, it depends on the man, their lifestyle and interests. However, jewelry can be the most versatile in a man’s wardrobe: a vintage tie clip, a signet ring, a wristwatch. These items are staples in many men’s wardrobes; why not make them vintage?

When it comes to vintage styling, what are some practical tips?

Vintage styling is a vast subject and one that I teach. In short, have strong sources of style inspiration, use that to build on your existing wardrobe, and be patient as your style will need time to change and settle into what looks best and what makes you most comfortable.

What’s the best way to store vintage clothing?

There are some who store their clothing as museums do, others simply press, fold and store them in trunks. Generally, avoid attics or basements as they can be damp and susceptible to vermin.

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