interview and illustration by ADAM ROGERS
Six years ago, when a friend in New York first told me about a guy named Bobby from Boston who had a “football pitch full of the finest menswear gems you can imagine,” I knew I had to see it for myself. And so, like countless vintage heads before me, a few weekends later I hopped an Amtrak train to Southie to pay my respects. Bobby was asleep on his famous rocking chair when I arrived, dwarfed by an antique oak cabinet holding the most impressive display of boater hats I had ever laid eyes on. We spoke for about an hour and have kept in touch ever since. Recently, I interviewed him about his trade via Skype.
What’s the most memorable piece you’ve ever bought, Bobby?
Ha! You are talking 40-plus years buying clothes, you know? The stuff I really remember are things I buy for myself and aren’t for sale. I was seventeen or eighteen walking around Times Square with 100 bucks my uncle gave me and I went into some of those men’s clothing stores where you could buy suits for $39.95. I remember buying a James Brown lime green shirt jack suit. That’s the funniest thing I can remember buying. It was 1967.
“I sell things at a good price. If they can make a profit, then that’s fantastic, everybody is happy.”
And the best piece you own?
I have an American men’s suit that was made in 1854, which I really like a lot. The problem is it’s like everything else back then, it’s black.
You have brilliant taste in classic British menswear. Where did that come from?
In my case, I think it came from the environment I grew up in. I came from a very mobile black family. My mother had a Caribbean and English aesthetic that she really showed us.
What defines a good taste to you?
Appreciating details and not just having a good eye in one dimension. Having a good eye allows you to adapt to anything — furniture, cars, interior design, the whole nine.
Vintage trends are always changing. How do you manage to stay relevant?
I’m more interested in trying to have a say in what is going to be worn down the road than trying to keep up with fashion. I hope I can continue to find the items that will be future classics that people come back to, like L.L. Bean duck shoes and other iconic things I was into before they became big trends. In the sixties, it was paisley and dark patterns similar to paisley. Nobody was buying them. I bought them by the shipload! I sold a thousand paisley shirts to a friend of mine on the Kings Road in London. I said, “Don’t sell them all.” But he sold them all, and he called me a few months later asking for a thousand more. I said you have to wait another five years before I find more. Suddenly, paisley shirts were hot again.
A lot of people deal in old clothes. Why do people call you the “King of Vintage?”
I’m very embarrassed and humbled by that. There are people who sell much more expensive stuff than me, and they do it a different way. They look for just the gems. I try and do it all: women’s, sleepwear, workwear, suits, kidswear, hats etc., so I can show it to the other kings of vintage and they can buy from me. I sell things at a good price. If they can make a profit, then that’s fantastic, everybody is happy.
Who’s your best-dressed customer?
I have quite a few. They live vintage, drive a vintage car. They look great and they know what they like, what fits them well.
Any advice for our readers on what to wear this summer?
I think the things to wear every summer are linen and rayon. Rayon is very cool. I don’t really like wrinkled linen, I like linen that can hold a crease. A nice Panama hat, a nice porkpie straw hat.
What about for amateur vintage lovers?
I’d tell those people who love it to persevere. When you’re looking through a barrel of stuff, really look through it and always go to the bottom. There are so many times that the best pieces are at the bottom, so don’t give up on the box. Be thorough, go through things piece by piece, don’t think you know everything, and you’ll find more. It will spark your interest and creativity, guaranteed.