Shawn Stockman | @shawnstockmanofficial
The founding member of Boyz II Men favors practical yet elegant timepieces, like the Jaeger-LeCoultre watch that Pierce Brosnan (right) sports in the “Thomas Crown Affair.”
First watch: A Sears special-edition Tigger watch my dad bought me when I was 7. It was really cool because his bouncy tail moved as I wound the watch.
Personal style: I like to call my style “practical elegance.” I can’t wear watches that are too “precious.” I travel a lot and I go to all types of functions. I can be in a tuxedo one night at a gala with politicians and dignitaries, next day I’m taking my daughter to school or running errands at home.
Watch count: I own about 14.
Best watch cameo: Pierce Brosnan and his Jaeger-LeCoultre Reverso in “The Thomas Crown Affair.” It’s one of my favorite movies, and his character was so fly! It matched everything about him and his character’s lifestyle! It was elegant, yet still masculine!
Celeb watch icon: John Mayer.
Watch you’re coveting: The Rolex Submariner. I always come back to getting another one. It checks all the boxes for me.
Favorite travel watch: My green-dial Rolex Sky-Dweller. I’m a time-zone hopper, so obviously this watch is ideal for my life.
Why wearing a great watch matters: Time is precious. And the type of watch one wears says a lot about how you value time. Or at least how you spend it. Advice for first-time buyers: Buy what suits your lifestyle! F – – k trends, wear what feels good. Express yourself (cue the N.W.A classic “Express Yourself”), lol.
Rebecca Ross | @tropicaldial
Ross is a vice president and head of sale for watches at Christie’s auction house. She says Don Draper’s 1960 Omega Seamaster watch from “Mad Men” (right) is a standout for her.
First watch: A Swatch that my father gifted me when I was around 13 years old. It was more meaningful than interesting, as it commemorated a time that we shared. I remember how the thick rubber band sculpted to my wrist — it was so comfortable that I never wanted to take it off! (Note: I did.)
Personal style: Generally, it is classic, timeless — but I do appreciate the unexpected.
Watch count: Around 15 pieces that my husband and I collect together. Once you truly understand watchmaking, it’s never enough.
Best watch cameo: Do you remember “Mad Men”? Great show, perfectly suited watches. Back in 2015, Christie’s sold some of the cast-worn watches in a special auction. Having the chance to sell Don Draper’s 1960 Omega Seamaster was especially memorable — not that he ever needed to know what time it was when he grabbed a cocktail. What makes this particular watch stand out is the cross-hair, black dial and that Jon Hamm looked extra cool wearing it on the cover of Rolling Stone.
Recent purchase: Back to the “unexpected,” it was a Patek Philippe 5098P. This is not generally anyone’s first Patek, as it is not the one you hear about most (read: Nautilus, Calatrava, Aquanaut), but we fell in love with it due to its more unusual shape and characteristics. It is a modern yet dressy watch — platinum with exploded numerals and a guilloche dial — that I dress up and he wears with a T-shirt!
Celeb watch icon: Jay-Z and Leo [DiCaprio] always seem to have the pinnacle piece of the moment, but I truly appreciate John Mayer’s knowledge of the watch world, along with his fascinating and eclectic collection. Tyler, the Creator also comes to mind, as his vintage ladies’ Cartier collection helped to create a new cultural paradigm.
Favorite travel watch: I’m from London, live in America and travel to Hong Kong and Geneva for work, so for me it is the Patek Philippe 5110. It is not as robust as some (thankfully, I’m not a hiker!), but it can allow you to easily read 24 different time zones due to its world time complication at the push of a button. The 37 mm size is also perfect for any outfit. Functional and chic!
Best watch to start a collection: For me, the right Rolex Oyster Perpetual or Datejust. These models may seem common to myself and my peers because we see them all the time, but for those just starting out, it usually signifies an effort or achievement — a first commission or bonus — and it always makes me smile to think of someone beginning their watch journey in that way.
Best watch to gift: Heirlooms are always most meaningful, but Patek, Rolex and Cartier are crowd-pleasers.
Rory McEvoy | @nawccmuseum
The executive director of the National Association of Watch & Clock Collectors trained as a watchmaker himself. He appreciates the TAG Heuer timepiece that Jenna Ortega (right) wore to the Met Gala.
First watch: The first watch that led me into the rabbit hole was a gift from my grandfather — a WWII-issue Leonidas timepiece, which opened the door to the fantastic world of Heuer.
Personal style: There’s a watch for every occasion. Simplicity and legibility are my go-to for workdays. Stainless steel case and a simple three-handed display for the office. An understated gold watch for dressy occasions, and for downtime, anything goes, from the bold stylings of 1970s sports watches to a modern take on a classic.
Watch count: Haha, way more than I need! During my training as a watchmaker, I bought non-runners for practice, and these make up the majority of my collection. However, there are a few special pieces that carry memories and stories that have great personal meaning.
Best watch cameo: The wonderful futurism of the crazy Hamilton watch that was made for Kubrick’s “2001: A Space Odyssey.”
Celeb watch icon: It was fun to see the pocket watch get a night out at the 2025 Met Gala. Jenna Ortega sported a great split-seconds chronograph by [TAG] Heuer, and Khaby Lame with his flea market-sourced collection of pocket watches. These are wonderful pieces of horological art and are so underappreciated right now.
Recent purchase: My last purchase was a Rolex for my wife. She chose a beautiful 1950s cocktail watch at an NAWCC event in Mesquite, Texas, this year.
Why wearing a great watch matters: A mechanical watch is a tangible technology with over 400 years of research and development behind it. It is a great thing that the ingenuity of the horological heroes of the past is not rendered redundant by less tangible technologies.
Favorite travel watch: My Seiko 7002 is a firm favorite. It is brilliantly robust and has been on my wrist for walks in the woods, diving and timing laps around Circuit Zandvoort in the Netherlands.
Watch you’re coveting: I am happy with the watches I own, and so it’s a great time to start refining the collection. I like to go to watch shows where there’s a good chance I will find an attractive upgrade.
Advice for first-time buyers: Stick to your budget and go for something that you like.
Best watch to gift: The gift to my wife was perfect because she picked it out!
Best watch to start a collection: For a first-time purchase, I suggest buying something new rather than vintage, and make sure it is something that speaks to you. It could be anything from retro digital watches by Casio to great dress and dive watches by Citizen and Seiko. For quirky displays, Mr. Jones has great novelty pieces. In short, there are some great buys to be had for under $500.
