Friends of Cad: Skip Powell
Some collectors chase rarity; Skip Powell chases history. A longtime friend of ours and the Head of VIP at Oliver & Clarke, Skip has spent decades shaping an eye for watches that have lived real lives, pieces with provenance, character, and the kind of documentation that makes the firm one of the most respected names in military and tool‑watch collecting.
We recently welcomed a small circle of friends for a private viewing of their collection, joined as well by Raymond, Oliver & Clarke’s timepiece specialist whose depth of knowledge brings another dimension to every discussion. Together, Skip and Raymond walked us through the watches that embody the firm’s specialty: purposeful objects with stories worth preserving. Settle into this conversation with Skip, where history, character, and craft come forward in a way only he can deliver.
Q: You’ve spent years in the watch world, chasing down rare pieces and the stories behind them. When did that instinct to find things first show up in your life?
A: I feel "instinct" is the perfect word to describe the "why" behind my love for hunting vintage watches. It's a challenge that involves multiple skillsets and requires a specific base of knowledge. I'm going to sound like a head-shrink here for a minute, but I think it comes down to the human desire for what we can't have, paired with the thrill of the chase. As for the "when," I'd say it started with vintage clothing. Vietnam-era BDU shirts and old Barbour jackets were probably the beginning for me. Finding either of those in good condition in my size is no mean feat!
Q: You’re known for tracking down watches most people would call impossible. What’s the hunt that taught you the most about patience or obsession?
A: Tornek-Rayville TR-900s have been my favorite watch for quite some time. Very few have ever been found. Without trying to brag, I've had the privilege of discovering three of them. Torneks are typically in the hands of the original owner, or with an immediate family member. Their watch typically represents a meaningful windfall for the owner, which is where the patience and obsession come to a head.Of course, the priority is making sure the seller is taken care of and that they feel confident in the transaction. Transparency and honesty are paramount. The reason I've had the opportunity to consign or buy the second two is because of that first transaction. The original owner was so thrilled with the outcome that he told his navy buddies that also had one squirrelled away.
Q: You’ve always gravitated toward watches with history. What draws you to a piece that’s lived a life before it reaches your hands?
A: Voyeurism? Romance? The transitive property of "coolness?" All possible answers that I wouldn't deny. A watch can be a wonderful vignette of a life full of experience. It harkens back the oral tradition of storytelling; the original owners of these pieces get to live on through them with their own saga.
Q: Before Oliver & Clarke, you carved out your own path in the vintage space. How would you describe that journey the pivots, the risks, the moments that shaped your eye?
A: Experience is hard-won, as any entrepreneur (not in love with the connotations of that word) would tell you. I started my first watch trading company at the beginning of the pandemic, which was definitely nerve-wracking. I had been trading as a side-hustle previously, but going full-time was a humbling experience to be sure. Mistakes are expensive in every sense of the word. If you can make them without losing your passion and bankroll, then you've got a chance. To keep my answer concise, I've certainly stepped on a few landmines. It's how I've recovered from a bad watch or made good a sour deal that has shaped my eye and my approach to business.
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Q: Now that you’re at Oliver & Clarke, what part of the role feels like the most natural extension of who you are?
A: What I truly enjoy about my current role is the team at my back. Linden and Raymond prove themselves time and again to be an invaluable source of knowledge and camaraderie.Uncertainty plagues the watch industry. To an extent I think that's heathy because it forces you to lean on the community for guidance. I'm lucky enough to be a part of a community that's built into where I work. No man is an island.
Q: The vintage watch world is full of nuance provenance, condition, scarcity, trust. What’s the biggest challenge in your corner of the industry right now, and how do you navigate it?
A: Finding the good stuff! Every day, fresh-to-market examples of good vintage watches are scarcer. You really have to pound the pavement to source great watches.
Q: When you’re evaluating a watch, what details do you look at first? What tells you instantly that a piece is special?
A: Most would say the "soul" of a watch is the dial. I tend to look at case condition first, however. I think it's much easier to find a watch with an excellent dial, than it is to find one with an excellent case. That said, case restoration is becoming more and more accepted by the community. You'd be hard-pressed to find a collector that can stomach dial restoration. Myself included.
Q: You’ve handled everything from understated classics to wild, one‑off finds. Is there a watch that still sits in your mind as the one that got away?
A: I touched on this briefly with the TR-900. Those I let go of certainly keep me up at night. The other would be a particularly fine example of a Rolex 6429 "Commando." I've only ever found the one and I let it go too cheap and too quickly. If the current owner is reading this, give me a call!
Q: You meet a lot of collectors. What separates someone who buys watches from someone who truly lives with them?
A: I would say the distinction is in the preoccupation with the financial element. If half of your attention is on preserving the condition of a watch while it's on your wrist, you aren't living.
Q: Your personal style has a quiet confidence to it nothing forced, nothing loud. How would you describe your approach to getting dressed?
A: Well, thanks so much for saying so! I haven't put it into words before, but I draw inspiration from observing people I respect and elements of my cultural upbringing. Also, my mom is probably the most stylish person I've ever met. I think part of her southern heritage puts an emphasis on dressing well as a sign of respect. You don't have the be the most formally-dressed in the room, but if you dress to a particular standard, people notice and appreciate it.I will also say my dad was a bit of an anglophile, who loved their sporting culture. Lots of tweed, Barbour jackets, wellies, and the like. Combined with my mom's sense of style, you get me.
Q: What’s one detail in your everyday style that feels non‑negotiable for you?
A: It's probably more about what I don't wear, or at least with any regularity. Shorts and sandals are strictly for the beach. Sneakers are for the gym. I'm trying to be less precious about those rules, though. The only true non-negotiable is I always leave the house with a watch on. It's always good to look like you know what time it is.
Q: Has working with vintage watches shaped the way you think about longevity and quality in the things you wear?
A: I think working with vintage is a by-product of how I buy clothes. "Buy once; cry once," right? I also love watching things I wear age with me. Brand new shoes never look right to me. The more milage, the better. Sometimes you have to get a little spendy to buy something that can go the distance.
Q: What’s inspiring you right now inside or outside the watch world?
A: I find inspiration in the people around me. How my wife parents our daughters. A friend rolling the dice on a new company. Another's clothing design getting the recognition it deserves. It's fascinating seeing how others manage risk and consider outcomes. I get to witness bravery, empathy, brilliance, and beauty every day.Those people give me the confidence to take big swings in my own life.
Q: Last one: what’s a watch you think more people should pay attention to not because it’s expensive, but because it has a story worth knowing?
A: Oliver & Clarke recently acquired a very special submariner. Those that know me, know I have a particular love for Tudor. Those that really know me, know that my grail submariner is a square crown guard 7928. Not only did we get a phenomenal example of that reference, it also has excellent and definitive Marine Nationale provenance. For the uninitiated (no shame in that), that is the French Navy. The watch is replete with dive logs, decommission papers, and other documents that I am currently translating. Man, I wish I could speak French.
Skip, thank you so much for your time. We truly enjoyed this conversation and the beautiful watches you brought to our attention. We look forward to seeing the other rarities Oliver & Clarke continues to bring to the forefront of collecting.
