If a very special, lucky someone on your list is due for a luxurious wrist upgrade this season, where do you start? You can't go wrong with Rolex, of course. And you especially can't go wrong buying pre-owned, which savvy collectors know is almost always the best play. 

To help drill down on your best possible moves, we turned to our friend Paul Altieri, the founder and CEO of California-based Bob’s Watches, who shared with us his four favorite holiday buys this season:

Rolex GMT-Master II ref. 126710BLRO “Pepsi”

"The black and blue “Batman” version of the reference 126710 GMT-Master II has received the majority of the attention this year, having just been released at Baselworld 2019," starts Altieri. "However, if I could only choose one modern Rolex GMT reference, it would be the “Pepsi” version that made its debut the year before. Mechanically speaking, the two GMT-Master II watches are identical; however, the red and blue “Pepsi” bezel insert of the ref. 126710BLRO provides a lot of the same colorful charm of the original vintage references but repackaged into a thoroughly modern and highly practical sports watch. Dealers have been sold out of the ceramic Pepsi GMT since its release, and used examples are still selling for well-above their original retail prices on the secondary market, meaning that this is also a model with investment potential, if you are lucky enough to get your hands on one."

Rolex Day Date 36 ref. 118238

"The Rolex Day Date President is an absolute classic and the quintessential luxury statement watch," continues Altieri. "Since its release in the 1950s, the core design of the Rolex President has changed very little; however, a number of updates and advancements have taken place over the years as Rolex continuously works to refine and improve its iconic design. The reference 118238 is not the most recent version of the 36mm Day Date, yet it offers many of the same updates and innovations that separate modern Day-Date watches from vintage references, such as its double-quickset movement, high-polish lugs, and solid-link President bracelet. Although the ref. 118238 possesses many of the same traits of the current-model, it can be purchased for nearly half the price, which makes it an excellent value among the various references available on the secondary market."

Rolex Daytona ref. 116500

"No list of Rolex watches could be complete without at least one Daytona, and while I absolutely adore vintage references with Paul Newman dials, their present-day values make the designs you can’t exactly wear-all-day, every day, at least not completely worry-free," Altieri tells us. "For me, the stainless steel ref. 116500 with its black Cerachrom ceramic bezel is the perfect Rolex Daytona for everyday life. First introduced at Baselworld 2016, the reference 116500 has been sold out at dealers worldwide ever since its release, and it consistently trades hands on the secondary market for almost 100% above its original retail price. However beyond its investment potential, and status as one of the most desirable watches in the world, the ref. 116500 is simply a fantastic luxury timepiece that combines all of Rolex’s most advanced technologies with rock-solid durability and truly classic design."

Rolex Datejust 41 ref. 126333

"The Datejust is the best-selling Rolex watch of all time, and today the collection is easily the most diverse within the brand’s entire lineup," Altieri wraps up with. "No other watch is available with nearly as many different options in regard to size, materials, dials, bezels, or bracelets, and the Datejust has been a cornerstone offering in the Rolex catalog since the collection was first introduced in 1945. The ref. 126333 is the most recent version of the two-tone steel and gold Datejust 41, and it represents the latest evolution of the iconic and instantly-recognizable aesthetic. Like other Rolex watches, the core design of the Datejust is absolutely timeless, and the reference 126333 brings it right into the present day with a modern 41mm case diameter and a new-generation Cal. 3235 movement."