The best vintage dealers are an amalgamation of career profiles. The job requires the eye of a collector, the savvy mind of a retailer, the deep knowledge of a historian and the patience of a hunter. They know immediately when to pull the trigger on a new acquisition. They operate on scarcity and demand. And, they know the buyers willing to pay top dollar for one-of-a-kind pieces.

While the profession allows dealers to explore their interests and passions, it is, at the end of the day, a business. Pieces are bought, sold and traded — it’s the nature of the job. That said, most vintage dealers still think about certain pieces they once possessed. To learn about these grails and hear some great stories, we reached out to a few notable dealers with the question, “What’s the one vintage piece you wish you never sold?”

USARP Parka

“Easy for me, we found an original USARP parka, United States Arctic Research Program, belonging to one of their scientists. It was a beautiful sun-burnt orange, really washed down from the elements and working in the field. Roy, my business partner and myself were in New York having lunch with two of the then Concept Designers at Ralph Lauren, back in 2011 this would have been. Over lunch we showed them proofs of our first book “Vintage Menswear,” and there it sat on page 250 in all its glory. By the end of lunch (they picked up the bill) they had convinced us to sell it. We agreed on a good price, and at the time we needed to take the deal though it hurt a lot, but we just couldn’t afford to hold on it to it back then. A year later the book came out and I literally did not stop getting asked about it. Without question it was the piece in the book that designers wanted to reference, still, now we will get at least one or two Brands a year asking about that piece.

I tried to buy it back a few times over the years and would always get the same response, laughter, it became a favorite in Ralph Lauren’s concept rigs which is totally understandable, but I don’t even get visiting rights anymore! I still wish I hadn’t sold it. It was one of the best outerwear pieces I have found over the years, and it has taken eight years to replace in our archive, we got approached back in January by a collector, different model but exceptional if anything superior. To be honest, if the new one hadn’t turned up I probably wouldn’t even be telling this story, but now I see the funny side, though I still shouldn’t have sold it ha!” — Douglass Gunn, The Vintage Showroom

Learn More: Here

Never Ripum Railroad Jacket

“I see vintage clothing and antiques dealers as coming in two basic types: the rarer type is in business primarily to make money and really doesn’t collect any particular item; the more common type is a collector disguised as a dealer. (I’m not casting any judgements on either type — just defining them for the purposes of my next few points.) I’ve been selling vintage clothes and antiques since about 1994 and I am absolutely and admittedly the latter type.

I recognized early on that I couldn’t keep everything I loved and I made a rule for myself that I wouldn’t regret selling things I had considered keeping (because I would never sleep at night, then). Once it was sold, it was gone and not to be obsessed over. However, there is one item I have regrets over because I didn’t actually choose to part with it. It simply disappeared from my possession — I lost it! I owned it for maybe nine months or a year and it was a fast favorite. It was a white railroad, or engineer’s, jacket. The brand was called Atlas and the zinc buttons had an image of the Titan god holding the globe on his shoulders. It had a huge oddly shaped pocket on the wearer’s left chest. It was in great condition and it fit me so well.

Atlas was a small brand which was actually a division of the A. Rifkin Co, a large Pennsylvania manufacturer. Rifkin also made a brand called Never Ripum. I happen to have the same model jacket in denim under the Never Ripum brand [see photo].

In the early part of 1999, I took a freelance job with a well-known design company. We were preparing a mockup of a store for a potential new brand they were planning. I rented and sold them quite a bit of vintage clothing and some antiques during the project. About halfway thru the job, I found a location for my own store I had been planning to open and I left the project to begin on my own. My best guess is that I left the jacket there and it was absorbed into the mass of merchandise that was floating around the project. By the time I realized it was missing, their mock shop had been dismantled and all the gear, dispersed throughout the company.

I’ve moved my home and business a few times since then and I always dream that I’ll open a box and there it will be, not lost, just misplaced. But 20 years later, I guess it is not to be. The vintage world is actually pretty small, so maybe I’ll re-find it in a shop in Japan someday. But I’m not obsessed with it or anything…” — John Gluckow

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Balloon Brand Coverall Jacket

“I bought a Balloon brand light blue and white large check patterned short coverall jacket with three pockets and five detachable buttons down the front. I believe it was made between 1900 to 1920 and I found it in the late ’80s at a vintage clothing store in Albany, New York. The chest pocket had an unusually cropped shape which was generally used for a pocket watch. Japanese call this “Kamenoko” which means turtle shell. I loved this jacket because of its nice simple design, wide spread collar, unique fabric and because it fit me perfectly. Kept it for over 15 years but eventually sold it to a friend of mine who’s a vintage dealer. Never have I seen the same or a similar jacket on the market again.” — Koji Kusakabe

Learn More: Here

1950 Harley Davidson WR

“I’m proud and grateful to have bought and sold vintage for a living most of my life, which has and continues to be a never-ending education about stuff, self and social behavior. It’s an unconventional competitive business that brings out the best and worst aspects of being nature in most folks including but not limited to love, hate, trust, jealousy, desire, curiosity, creativity, fear, aggression, doubt, respect, disrespect, greed, success, failure, realistic expectations, unrealistic expectations and of course regret.

I’m not much of a collector and countless objects have passed through our hands during the past 50-plus years of business, some of which I painfully regretted selling at the time not knowing their true value but [they were] ultimately beneficial parts of the learning process. When it comes to regret, this business has taught me, “Let it go, learn the lesson and move on.” With that said and as much as I try, I still regret selling my barn-fresh 1950 Harley Davidson WR and, in spite of all logic, may never fully get over it.” — Mark Fogwell, Worn Over Time

Learn More: Here

’70s Patched Lee Hippie Jeans

“Over the years, I have acquired so many pieces that I wish I wouldn’t have sold… One item that comes to mind is a pair of patched hippie jeans from the 1970s.

I was at a flea market a couple of years ago not expecting to find anything. I asked a dealer if he had any clothing and he said no but a dealer around the corner has a great pair of jeans stashed away in his truck. I asked the man if I could see the jeans.

When he brought them over I couldn’t believe eyes. This was one of the best pair of jeans I had ever seen! They were a pair of Lee jeans from the early 1970s. The original owner had artfully covered the majority of the jeans in leather and embroidery by hand. In my opinion, these jeans were museum-worthy. Possibly for a retrospect on hand-embellished pieces from the 1960s to ’70s.

As much as I wanted to add these jeans to my collection. I decided to pass them on to another collector that had the space to properly display them. They deserved to be showcased as they are a piece of art. I often think about these jeans but I feel good knowing that I found them a good home.” — Melissa Howard, Stock Vintage NYC

Learn More: Here

Carhartt Stifel-Fabric Overalls

“There was a guy in the Seattle area, I won’t name him, he was a dealer. This must have been 10 years ago or so. He called me and said that he had this crazy piece that was a pair of Carhartt overalls. And I don’t know if you’re familiar with a fabric called Stifel fabric which is usually a printed fabric — normally it’s just a dot pattern. It goes up and down the piece. That Stifel sort of fabric is the most desirable, probably, besides denim in the collectors’ world.

So I go to his warehouse. Not only is it what he says it is, but instead of a standard dot pattern, for Carhartt, they used a heart pattern. So small hearts ran up and down the piece. I had never heard of, seen, nor had reference to a piece like that at all. Just if I could imagine the perfect piece, I different would have imagined the way that piece was. It was very early, it was a buckle back-piece, so that put it somewhere in the 20s or 30s. It was a little bit big, but generally speaking an excellent size.

So I made an offer, I think at the time, my offer was $6000. So he says, “You know what, I’m sorry. I already sold this to somebody else to buy this, they wanted it. So I’m waiting to see what they’re going to do.” I was furious. In any kind of business you’re in, you can’t let your personal feelings get in the way of business, because there’s not very much business to do. So I didn’t act furious, but I was beside-myself furious because it was one of the coolest pieces I’d ever seen. He had called me to come out, I had the money, of course, for the deal. Then at the last second, he says these guys have first right of refusal.

So I called the guys that had the first right of refusal. I said look, “I’m looking at this piece, I don’t know if you gotta have it or don’t have it, but if you guys back down on this deal, and I get to buy it, I’ll owe you one and I’ll make sure it’s a very rare find.” I knew these guys pretty well, and they said, “No, no we’re not doing that.” So I’m more mad, I’m a little bit embarrassed, and I’m just standing there for hours, trying to figure out how I could get this. It was a Friday. So I went home and I was mad, literally, all weekend.

Then the guy calls me on Sunday and says they passed on the piece. This piece now in Japan is a $50,000 piece at this point in the game. It was unbelievable that they had passed up, I couldn’t imagine the piece coming into my hands after the scenario went down. That was a piece that I wish I could have kept. I think at the time, we sold it for between 15 or 20 thousand, we made our profit. By the way, I have never seen another version of that or anything remotely like that since then.” — Larry McKaughan, Heller’s Cafe

Learn More: Here

Nothing

“Not too many people know me. Mostly, I work with friends and family. Even when I do the store, I never promo it. Even if I know someone, I never tell them my store is there — it’s only for friends and people I feel comfortable with. And even then, I always think, “Objects are still objects.” I get more from a feeling. If someone likes something more than me, I’m happy if they have it.

One thing I learned: I see the soul from people who made the object. When I see the object, I know how much soul they put into that piece. So when I learn enough, I let it go to the right person who will love it more than me. Someone who will look at it as an object and relate to the feeling more than the cost of money.

The first pieces I got from the flea market in New York were the AJKO (Air Jordan Knock Out) deadstock sneakers. I got them from the Chelsea Flea Market for $5 and gave them to a sneaker store in Singapore. They display them.” — Prasong “Pat” Kanhasura, Bangklyn

Learn More: Here

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