Holiday season is coming, and that means watch giving season is here! Watches have the potential to be one of the most sentimental gifts out there, and the holidays are just one of the many times in which watches can mark a meaningful moment. If you’re looking for the perfect watch for a special person in your life, here are some of the primary considerations you should assess in choosing a gift that’s just right.

A thoughtful approach

While a watch gift naturally carries emotional weight, getting the right piece makes it all the more meaningful and appreciated. According to expert watch consultant Samantha Haizelden, the key to getting the selection right is all about knowing the recipient. “I think that someone's personal style and lifestyle are equally important. I like to match a person to a brand and would recommend a Hamilton for an adventurous teenager or a Cartier for an elegant woman,” she said. Considering how the recipient will wear the watch—their lifestyle, personal tastes, and daily routines—not only ensures the piece is right for the recipient, but also demonstrates the thought and care invested in your choice. In many cases, the thought process behind the selection can be of equal importance to the gift itself. 

Avid watch collector and journalist Troy Barmore suggested that the most meaningful gifts bridge the gap between the gift giver and the recipient: “The best gifts are those that speak to a shared meaning,” he said. Once more, this underscores the essential value gifts hold, formulating an emotional bond that is more important than the price tag of the gift. As Haizelden put it, “A shared moment or inside joke will make the watch all the more special.” 

Modern vs. vintage

Once you’ve identified the genre of timepiece for your gift, you still have some further considerations. For example, how should one consider the difference between going for a contemporary piece and a vintage classic? Barmore indicated the unique qualities of each, suggesting that, “A new watch starts a new story with its owner, whereas vintage pieces continue the story of the watch.”

When commemorating a milestone or important occasion, opting for a contemporary piece often metaphorically matches the type of event. For example, a graduation is a commemoration of moving on to a new chapter in life. This lends itself to a contemporary piece, one which the recipient will associate with embarking on that new chapter. Keeping in mind Barmore’s differentiation between new and vintage pieces, a holiday gift could be a great occasion to explore vintage, as long as the piece suits the lifestyle and everyday needs of the recipient. 

Meaningful memories

Both Haizelden and Barmore reflected on meaningful horological gifts they’d been involved in. Barmore told me about his beloved Rolex Submariner, a gift from his father at his graduation. He said, “It was a watch he wore as a work watch for years, building multiple houses while wearing it. It is a prized possession and represents hard work, and my relationship with him.” To Barmore, the elements that made the watch meaningful had nothing to do with the watch itself, but rather what it represented: the role it played in his father’s life, and by extension, his own. At these life-defining moments, the added provenance of the piece helps build its story and significance. 

Similarly, Haizelden described picking out the perfect piece for her sister. “A big fan of everything Japanese, my sister had booked herself a trip to Tokyo for her birthday. I bought her a Mr. Jones Robotto Shi which she not only took with her, but she sent me a great photo of her wearing the watch with Mount Fuji in the background,” she recalled. There’s no doubt this piece will become a memory of the trip as well as a special memento of Haizelden’s relationship with her sister. 

Don’t forget the extras

Finally, if you’re looking for the perfect stocking stuffer for the watch lover in your life, Haizelden suggested seriously considering watch accessories. Among her suggestions are “additional straps to change the look of an existing watch, travel cases to safely store watches, practical gifts such as tools and even more unusual watch memorabilia.” For watch collectors, there are tons of options, including hundreds of incredible watch books!

In the end, the right watch gift isn’t just about its specifications or fine horological details—it’s about the story it represents for the gift giver and the recipient. Whether you choose something new to mark a fresh chapter or a vintage piece with a life already lived, the most meaningful watch is the one chosen with thoughtful intention. With some thoughtful reflection this holiday season, it’s the perfect time to give a gift that becomes a future cherished companion.