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Customer Spotlight: Dexter Wimberly


One of the great joys of selling high quality luxury watches is getting the opportunity to interact with our customers after the fact, learning why they chose the specific model they did and seeing how they live with their purchase day-to-day.

Dexter Wimberly

Meet Dexter Wimberly

One such client is Dexter Wimberly. Originally from New York and now living in Japan, Dexter started out in the advertising industry, working with such blue-chip companies as HBO, Virgin America, Adidas and Coca-Cola.

After 13-years, however, a new challenge was calling. His career had brought him into contact with many struggling yet extremely talented artists, and so he co-founded Art World Learning. An online education service, it provides courses to teach artists about the business side of their profession and help them become more financially empowered.

Since then, Dexter has also become a senior critic at the New York Academy of Art, and established himself as an in-demand independent curator.

But in March of 2020, even bigger changes were stirring. His annual 30-day trip to visit his wife’s family in Hayama, Japan was extended due to COVID quarantining regulations. With sitting still apparently not in his nature, he took the prolonged sojourn as an opportunity to establish the Hayama Artist Residency.

The program, open to artists from all over the world, gives them the opportunity to fully immerse themselves in Japanese culture and also meet some of the country’s most influential curators and gallery owners. With the establishment of the residency, Dexter decided to sell his home in New Jersey and move to Japan permanently.

Dexter Wimberly with a Gold Submariner 116618LB

So… What’s on your wrist Dexter?

Clearly a man who enjoys the finer things in life, as well as someone with a highly developed visual sense, we were delighted to sit down for a call with Dexter to discuss the stunning blue dialed Rolex Submariner ref. 116618LB he acquired from us earlier this year.


TWS: So, what are you wearing on your wrist?

DW: I’m wearing my Sub that I bought from you guys! It never occurred to me that my daily wear would be a gold Sub!

Dexter also touched on the concern that one might have about the inevitable wear and tear that comes with sporting the same watch everyday.

DW: There’s a balance between enjoying a watch and worrying about scratching it. The idea of a watch losing value because it’s lived a life is a false idea. Timepieces are built to last and handle day-to-day activities, and some of the most interesting and valuable vintage watches are the ones which show the most wear.

Some people want to buy a watch and put it in a safe while it appreciates. From a financial standpoint, there are better ways to increase your money. It’s better to wear the timepiece and enjoy it.

A Tudor Black Bay is another favorite of Dexter's.

Watch History

Dexter has a deep fascination with history in general, and watches in particular. As an artist, he loves to learn about the story behind watches, so we wanted to delve a little deeper into his own history with them.

His first luxury timepiece was a steel Rolex Oyster Perpetual with diamond markers, bought in 2000 in NYC. He later decided to purchase the anniversary green dial GMT-Master II, ref. 116718, but sold the watch over concerns about wearing such a valuable watch around New York, especially on the train from Brooklyn. His current situation couldn’t really be more different, living in a small Japanese coastal town with a population of 33,000 and practically no crime.

He now, along with the gold Sub, wears a Tudor Black Bay 58.


DW: I wear the Black Bay on the beach and on walks with the kids. It seems like a watch I can wear anywhere and do anything with, which doesn’t make any sense because it’s still a $4,000 watch! Ten years ago, I would’ve treated it like it was a gold Sub.

Other people who own very expensive watches don’t stress about it because of where they are at in their lives. If you have a hobby, it should bring you joy. If it brings you stress, you either need a new hobby or you’re doing it wrong! (joking!)

Dexter one day plans to give his watch to his children.

More than just a watch

TWS: Are you planning on giving your oldest son your Black Bay?

DW: Yes, but maybe after college. And he’ll probably get more than just the Black Bay.

TWS: It was my own father who actually introduced me to the industry. He told me you might hate your first suit or car, but no one has ever hated their first watch, no matter what it was.

DW: Absolutely. We all take pride and joy in what we put on our wrist. I want this to be something that I can have beside me when I create memories.


Speaking of making memories, Dexter will have been married for 10 years next May. When he met his wife, he says, she had no interest in watches whatsoever. But seeing Dexter engage with the hobby has obviously rubbed off and she will now send him pictures of models when she is out and about to get his opinion.


DW: It really is infectious, the passion you have for something. It really does infect other people. For example, when we first moved to Japan, we needed to buy a car, so I went online. I went to show my wife one I’d picked out and accidentally switched tabs to a picture of a Patek 5990R and she said, ‘Wow, that’s nice. You know, you should probably get that instead of a car!’ so that was a pleasant surprise!


That Patek 5990R is a watch Dexter can see himself purchasing in the future, and he has friends with Pateks who love them. Yellow and rose gold models really appeal to Dexter.


DW: If you’re going to spend a ton of money on a watch, it might as well be a precious metal.

If money were no object and I had to pull the trigger today, that 5990R would be it. I think it’s gorgeous.

Dexter Wimberly

Art and Watches

If someone with Dexter’s artistic knowledge and experience loves the look of a watch, then chances are it is a beautifully executed model. But do others in the art world share his appreciation for luxury timepieces?


TWS: How does the art industry view the watch world, since art pieces are usually one of a kind?

DW: I think that the people in the art world who know anything about timepieces understand the artistry and respect it tremendously, because they know that when we’re talking about the higher end of horology, we’re talking about brands that are doing hand finishing and hand painting enamel. That requires a skill level that’s comparable to a painter, to a sculptor.

Most people don’t know enough about the watch world to get that, so they think there’s some machine in Geneva just stamping, stamping, stamping!

The other thing that your question makes me think about is how the art world is actually attempting to adopt the technology of the watch world to the extent of transparency around sales and transparency around the provenance of a particular watch. 

The art world has been shrouded in mystery for decades and the art dealers benefit from the mystery because they don’t necessarily have to make their prices known publicly. So, you walk into a gallery in any major art center or district, and you never see a price list. So, you ask the price of the painting and you’re relying on the person to tell you the price, which is probably not the same price they tell someone else whom they have a longer buying history with, which is also not the same price they tell a museum who wants to buy the work.

And so, the relationship component in the art world really dictates how much you end up paying for something. And there is very little transparency.

So, the art world has a lot of people, particularly younger, more tech-savvy people, who are attempting to make things more transparent so that you’re not really relying on the person’s sentiment to determine the price.

There are definitely artists and collectors in the art world that recognize that watchmaking is an art form in and of itself and they appreciate it and appreciate it as such.


Dexter was kind enough to give up a lot of his time to share his views and answer our questions. But we wanted to sign off on our call with a couple more about his experience dealing with The Watch Standard.


TWS: How did you find us?

DW: I found The Watch Standard online via Google. I then did further research on some forums and looked at your BBB rating. This built up my trust.

TWS: Why did you decide to purchase from us?

DW: I thought your website was very well done and when I asked questions, they were answered quickly and professionally.

I’m really happy we took this time to talk. I really admire your business and just wanted to reiterate that the process of buying the watch from you guys and the customer service, and everything was really excellent. So, you should definitely give those people that were involved in my transaction a pat on the back and say you guys did an excellent job!


Our gratitude goes out to Dexter for his time and kind words. To learn more about his work, visit www.artworldlearning.com and www.hayamaresidency.com

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Rolex Bluesey Used-Face2