Photo Report: Watch Spotting At Oliver Smith Jeweler’s Annual Cars & Cigars

The week before Christmas, as families and businesses alike host parties and toast to holiday cheer, Oliver Smith Jeweler of Scottsdale, Arizona, gears up for a different sort of festivity. For the past 20 years, the destination watch and jewelry retailer has been hosting Cars & Cigars, an awe-inspiring spectacle of motorized enthusiasm. Drawing from the broad car collector community around Scottsdale, 100 classic and collectible cars were arranged in front of the long-standing store. I attended the event this past December, and the parking lot was packed; thankfully, there was also no shortage of interesting watches to capture. 

While previous years saw a broad cross-section of cars, in celebration of the 20th anniversary of the event, this year focused (mostly) on pre-1975 cars. The front row captured the bedroom posters of a previous era–a Ferrari 250 GTO, a Ferrari 250 LM, a Lamborghini 350 GT, and an Aston Martin DB5. But above and beyond the automotive eye candy, the event is also a spectacular show of community. You see, while the invitations to the event are only sent to clients, locals in the know are all welcome to partake in the festivities, including food catered by local restaurants, ample refreshments, and of course, cigars.

The event has become a fixture in the holiday calendar for the broader Scottsdale area. But it was not always that way. The event began organically, with a handful of clients coming by the store (during special holiday hours) for some last-minute Christmas shopping. Several attendees arrived in rather special cars. Slowly, a few cool cars became an impromptu gathering. By the time Oliver Smith was ready to relocate to the location of their current flagship, access to a parking lot of sufficient size was non-negotiable. From there, the community and collectors have followed.

“The crossover between serious car collectors and watch enthusiasts is very real, and Cars & Cigars has evolved into an event that allows us to share that passion in a relaxed, authentic way.” Oliver Smith said. “Hosting it at the end of the year is especially meaningful. It is a time to take the car out for a Sunday drive, spend time with family and friends who are in town, and celebrate another great year.”

It’s an impressive, fun, and accessible event with a lot of interesting watches among the collected arrangement of cars, old and new. Scroll on for a selection of my favorite shots from 2025’s annual Cars & Cigars.