Aficionado Feature: Henry Flores, founder of Classic Watch Club

We sat down with Henry Flores at Pier 76 (Classic Car Club Manhattan) for a cocktail and a conversation about life, watches, and all things hes passionate about. Henry is a friend, a mentor, a husband, and a father. 

Aficionado Feature: Henry Flores, founder of Classic Watch Club

By Hubert Kolka


 a·fi·ci·o·na·do - noun

a person who is very knowledgeable and enthusiastic about an activity, subject, or pastime.


We sat down with Henry Flores at Pier 76 (Classic Car Club Manhattan) for a cocktail and a conversation about life, watches, and all things hes passionate about. Henry is a friend, a mentor, a husband, and a father. He is the founder of the Classic Watch Club, a private curated community for passionate watch aficionados with over 200 members worldwide. CWC has been featured in the Robb Report, NY Times, WSJ, GQ Magazine and the NY Post. 

The club was founded in 2019 at the Classic Car Club of Manhattan with the intent of Henry gathering his closest friends in the watch community. From its humble beginnings, the Classic Watch Club has become a gathering place for the whos who in the watch world (and myself, I aspire to one day have a fraction of the knowledge these guys do). Classic Watch Club meets twice a month once in person, and once virtually.  The virtual meetings are a continuation from the pandemic and feature prominent guests presenting on a variety of topics from the state of the market, to the most recent Frankenstein Speedmaster.  

Hubert: Henry, thank you for joining me today, I appreciate you. Youre our first Aficionado feature, tell our audience who you are. 

Henry: I am an aficionado of all things that allow one to live la Buena vida or the good life as Dominicans like to call it. I love great design which explains my love of cars, horology, and mid-century furniture.  I am also an epicurean that loves extravagant meals and pairing them with the right wines while gathering our family and friends whether it be in NYC or at The Maverick, our Mid-Century home in Woodstock, NY.

Hubert: Let's dive deeper into your past. Tell me about your formative years, and your professional and personal lives.

Henry: I was born in the Dominican Republic, and raised in the housing projects of Spanish Harlem by a single mom. At 14, l obtained a full merit scholarship to attend All Hallows High School via Student Sponsor Partners, a program which mentors and sponsors inner city students to attend a private high school. From All Hallows, I went on to graduate from Middlebury College and NYU Stern School of Business. 

When Im not running the Classic Watch Club, Im a real estate professional with over 20 yearsexperience in acquisitions, RE development, finance, and strategy. I am also the chair of SSPs junior board where over the years we have raised over $1M for the organization that helped transform my life. I also mentor and sponsor SSP students, and I have been doing it for over 20 years.

 WA Note: Henry resides in his native Spanish Harlem with his wife, Dr. Veronica Lerner, a talented Surgeon, and their 7-year-old daughter, Mia.

Hubert: What sparked your interest in watches? Can you recall the moment or event that ignited your passion for watches? 

Henry: In 2004 I was visiting my family in St. Thomas, USVI and while I was walking around the duty-free shops in Charlotte-Amalie, I saw a TAG Heuer 1964 40th anniversary Carrera, a 39mm Chrono with a racing red seconds hand and had to have it. I was always fascinated with all things automotive, air travel, the space age and anything mid-century modern so the natural course from the Carrera re-issue for me was an Omega Speedmaster, Breitling Navitimer, and in 2016 I acquired my birth year 1675 GMT and went down the vintage rabbit hole. From there Ive gone on to own a 1665 Double Red Sea Dweller and several vintage Speedmasters. 

Hubert: For as long as Ive known you, you have been @HarlemVintage on instagram, but in the last few years of our friendship you made a slight transition into modern pieces. Tell me about your experience with both worlds. 

Henry: As I mentioned I started out a modern collector in 2004, with the TAG 1964 40th Anniversary Carrera and an Omega Speedmaster but those classically styled modern watches planted the seed for my love of vintage watches. I love Vintage due to the challenge of finding a piece in pristine condition and navigating the minefield that is vintage watch collecting. I believe in wearing all my watches whether they are modern or vintage.  My journey into modern pieces came because of me wanting to wear certain watches without worrying about them as much, but also modern watches presented a new challenge in their difficulty to obtain.  

Hubert: You have a daughter, any special watch you have in mind for her Sweet 16 or 21st birthday or any other special occasion?

Henry: Mias favorite watch in my collection is my birth year 1675 which she always picks out for special occasions.  This watch will eventually be hers. When she graduates college, she will get my modern BLRO Pepsi. 

Hubert: What role does watch collecting play in your life beyond the acquisition of timepieces? Does it serve as a form of self-expression, a hobby, or something else entirely?

Henry: Watch collecting for me is about the people you meet as part of this crazy way of life.  During the pandemic, my wife suggested that I start doing virtual meet ups and Classic Watch Club was among the first to do them. As a result of our virtual meetups, the CWC community expanded dramatically, and I made some amazing new friendships that have carried over into the real world. For me, watch collecting is about community and making friendships.

Hubert: How would you describe your watch collection? Are there any particular themes or styles that dominate your collection?  

Henry: My watch collection consists of classic stainless steel sport watches ranging from Vintage Rolex and Breitlings, to modern Rolex and APs. As you know, I paired down my collection quite a bit to fund The Maverick, my familys 5-star vacation rental home in Woodstock, NY.

Hubert: That is true, the Maverick is stunning and the memories made there with your family outshine the few old watches you had to give up *wink* 

Hubert: What criteria do you consider when selecting watches to add to your collection?

Henry: For Vintage my criteria is condition above all else.  I want to be as close to unpolished as possible. I say close because finding unpolished watches is becoming harder, and with all the case enhancements being done, its getting harder to tell them apart.  I am a sucker for a killer dial with even patina and as you know I suffer from an extreme case of bezelitus which I contracted from Brian Gartside, a close friend, and another insane 1675 bezel collector. GMT inserts are a huge part of the charm of the watches and swapping them is like having a different watch on your wrist every time.

Additionally, I always buy the original bracelet that came with the watch but I do not care much for the box and papers. You cant wear those, and I wont pay a premium for them. That said, the provenance of the piece is very important if it can be validated.

Id say my collection primarily consists of chronos, GMTs and divers.  I love how their design incorporates form and function. I recently picked up a virtually NOS 809 Breitling Cosmonaut with a 24 hr dial and integrated slide rule originally designed for NASA Astronaut Scott Carpenter when he first orbited the earth. Looking at it evokes for me an era of romance and endless possibility when humankind was literally reaching for the stars. It also has a cool Mid-Century aesthetic to it which I love and goes well at the Maverick.

For modern watches, I like to consider their significance in the world of horology, the beauty of their overall design and finally its robustness. 

Favorite brands Id say have to be: Audemars Piguet, Breitling, Rolex, and Omega as those are the brands that have been in my collection in different forms in my 20 years of collecting.I've really gone down the vintage Breitling collecting vortex thanks to my friend, Fred Mandelbaum, Breitling brand historian and fellow CWC member.  I just received an incredibly rare vintage Breitling 2005 Super Ocean which Fred helped me vet.

Hubert: Time for some tough questions: Do you have a favorite watch in your collection? Whats the story?

Henry: This is like asking someone to pick their favorite child, but like many their first born holds a special place in their heart. For me thats my birth year 1675 GMT, due to it clicking all of the boxes for me as a lover of vintage: Case, Dial, Patina, a killer insert and its connection to aviation specifically being developed for Pan Am pilots. I have about 7 or so vintage Pan Am cocktail glasses used during flights in the 1960s that I love using while wearing my 1675. I also love my two 809 and 2005 Breitlings though.

Hubert: How do you approach the process or the hunt of researching and learning about different watches? What resources or communities do you rely on to expand your knowledge? 

Henry: The main reason why I started Classic Watch Club was to build a community of experts that could provide advice to one another and help each other navigate the tricky world of vintage watch collecting. I am fortunate to have access to amazing friends and fellow CWC members  like Eric Wind, Geoff Hess, Jeff Stein, John Cote, Fred Mandelbaum, and Andrew Hantel among many others. I do my own research first by looking at auction catalogues, various blogs but before I pull the trigger I consult my CWC network.  When purchasing my NOS, Breitling 809 it helped to have Fred Mandelbaum, the worlds foremost expert on Breitling, actually physically vet the piece and give the thumbs up.

Hubert: What advice would you give to someone who is new to watch collecting and interested in starting their own collection?

Henry: Join a watch community whether or not you have any watches this way you get to try on a ton of different watches without shelling out thousands! Finally, collect the watches that you love but be cognizant of whether it is better to buy it used or new depending on value. 

Hubert: Tell me about Classic Watch Club. What sparked the idea? Who were the key people that helped you out early on?

Henry: I founded the Classic Watch Club, after joining the Classic Car Club of Manhattan. For a few years, my closest friends and I would meet at various restaurants throughout New York City but as our collections grew, I wanted a more secure and consistent meeting place to host our small crew. Brian Gartside and Gee Li are my closest friends in the hobby, and we would meet monthly and have our collector friends invite the friends they thought would be a good fit and the club grew via personal invitation. Michael Prichinello, who is part owner of the Classic Car Club kept having members come up to him asking who these crazy guys with all the watches are? Mike approached me about making our meetups official within the Classic Car Club.  

Hubert: What has been the most memorable experience for you with CWC?

Henry: The most memorable watch experience was recently doing a bucketlist trip to Geneva with  5 buddies of mine from CWC to Watches and Wonders this past April. We were there for over a week staying at a large Airbnb and I arranged private tours with Audemars Piguet, Vacheron Constantin, Tag Heuer and JLC. We had a blast and met some amazing collectors from around the world and made some great relationships with the heritage departments of these esteemed brands.

Hubert: Where can people reach you if they want to get in contact about joining the community? 


Henry: Prospective watch club members can reach me via IG at HarlemVintage or Classic_Watch_Club.  There is a close vetting process to ensure safety and the integrity of our community.

Hubert: What else are you passionate about? We're both BMW guys, so tell me about the M. 

Henry: In the watch world, people fantasize about being a one watch collector and the freedom that would bring.  In the car world, I am a one car collector.  Since 2007, Ive had the pleasure of owning an 03 E39 M5 in titanium silver with black interior and wood trim. I purchased the car from a State Trooper in Long Island for my 28th birthday with 32,000 miles on the odometer.  When purchasing the car I lamented that I would never be able to fully drive it the way it was meant ot be driven.  The trooper promised me he would arrange something if I purchased the car.  After the title was signed, the trooper got in his police cruiser, radio ahead to his buddies and said to keep the roads clear. He escorted me on a 3 mile pedal to the metal experience with his sirens blariing and lights blariing in front of me.  Back to the M5, this car was my grail car and I baby it to this day. It's driven me to vacations, weddings, funerals, but most importantly the birth of my daughter, Mia. To me the E39 M5 represents a bygone error in BMW, when the cars were proverbial wolves in sheeps clothing and the E39 M5 was and still is the leader of the pack.

Hubert: Tell me about the Maverick. 

Henry: The Maverick is a fully 1964 Mid-Century Modern home which sits on 4 acres of former state park land and is in Woodstock, NY. We purchased the home during the Pandemic as an escape from the city. The home had amazing bones, but it was in desperate need of repairs. We did a full gut renovation which took 6 months.  My wife likes to call the Maverick, Henrys Mid-Century Museum as it is a time capsule of the designs of that era including several Eames chairs, a womb chair, George Nelson and Paulsen light fixtures throughout and vintage film posters from my favorite director, Alfred Hitchcock. In addition to owning, I also manage the property as a short term vacation rental and act as a sort of concierge for our guests. We have over 60 five-star reviews and counting. We love providing our guests with an unforgettable experience by providing a fully stocked kitchen, a masseuse that does house calls, and a special gift at check-in for every guest.

Hubert: Henry, thank you for doing this with me, I appreciate your time and the community youve built.  

To book a stay please contact Henry via his IG account at Midcentury_Maverick or email: Mention Wrist Aficionado for a discount! 

Are you an aficionado? Id love to interview you, email me at and lets talk soon! 


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