Collector’s Corner: Phillip Toledano Talks ‘Strange Joy’ of Watch Collecting

Jeremy Freed December 15, 2023

There are plenty of watches plastered across social media, but the ones Phillip Toledano posts are different. An evangelist for all things strange and beautiful, the NYC-based photographer (@misterenthusiast on Instagram) has featured everything from the delightfully blocky 1970s Rolex King Midas to Louis Vuitton’s first ever watch, the 1988 Monterey II, on his feed. Here, we ask Toledano to define his distinctive tastes, outline his rules for buying watches, and offer tips for surviving the “feeding frenzy” of the collector market.

What was your first ever watch?

I’ve actually still got the very first watches I was ever given. The first was a weird little gold-coloured watch on a red bund strap and the second was an early ‘70s Timex LCD digital watch.

How did you become a collector?

I lost interest for decades, but then I sold a car to Ben Clymer, the founder of Hodinkee, and we became friends. From there, I gradually got sucked into the black hole of watches.

What specifically do you like about watches?

I’ve always liked obscure things and stuff that other people have forgotten about. It’s a form of cultural and historical exploration. It’s like reaching an undiscovered continent — you arrive and there are like 12 other nerds on this continent who also happen to like this same weird thing.

How did you get hooked on 1970s watches in particular?

I think I just started looking at them a bit more. That ‘60s and ‘70s integrated bracelet stuff is so different, you have to look at it for a while to even begin to understand the beauty. It’s the idea of creating this single sculptural unit that’s not just a watch head and a dial, and the incredible craftsmanship that went into making that. I also think that it’s just the pathological contrarian-ness of it — always wanting to have things that aren’t particularly popular. I take a strange, perverse joy in evangelizing the things that I like.

How do you choose your pieces?

There’s a kind of Venn diagram between: “Is this interesting enough?”; “Is this beautiful?”; “Is this enough of a bargain for me to sample without completely losing my shirt?” I started with a white gold Patek Philippe backwinder I bought off eBay and, after that, I was hooked. Then I threw myself into the almost borderline-unwearable-but-actually-glorious integrated bracelet stuff.

How many pieces are in your collection right now?

Maybe 30. I’ve got seven or eight Rolex pre-Daytonas and three or four Cellini King Midases, a dozen ‘70s Pateks, and a couple of ‘80s and ‘90s things, too.

These are all such rare pieces, do you wear them outside in the city?

I wear them all the time. I try to wear a different one every day unless it’s raining. That’s what makes it such an insane affectation if you own only vintage watches, because you have to have one watch that you can wear when it’s raining or snowing or whatever. But then, you know, I’ll be doing the dishes in my lapis dial Midas and I’ll think, “Oh, shit. I should probably take this off.”

Have you ever regretted a purchase?

Oh, absolutely. You can never tell if it’s for you until you see it physically. Sometimes the watch will arrive, I’ll open the box and be like, “I guess I’m gonna have to sell this.”

If someone wants to get into vintage watches, what’s a good place to start?

I would say ‘70s Patek. You can find an amazing watch for five or six grand. Those things were handmade, and it’s incredible the amount of workmanship that went into them. Also, from an authenticity standpoint, you’re going to be safe with those watches because it’s not worth anyone’s time and effort to do anything to them.

Do you think about appreciation or flipping at all when you buy watches?

When I collect whatever it is — whether cars or watches — it seems like a stupid endeavour to begin with. So I feel like, if I am going to spend all of this money, number one, I must like it. That’s the unbreakable rule. Rule two is that if I wanted to sell it, would it be relatively easy to sell? I know a lot of people have this sort of visceral rage towards flippers, but my answer to that is not to participate in that economy. I always steer well clear of those kinds of watches because I don’t want to be a sucker. I don’t want to participate in a feeding frenzy. To me, it’s not what I find interesting about collecting. I always say that collecting is a reflection of your own imagination, and if your imagination only reflects everyone else’s, then it’s no imagination at all.