THESE DAYS WE’RE inundated with so many new products and trends cycling at a disorienting pace that heirlooms — enduring items with elevated status, a treasure handcrafted to pass down a family line — have heightened gravitas. And there’s no item better suited to mark a lineage of milestones than a well-made wristwatch. It is the heirloom of heirlooms. In a more spiritual sense, watches remind us of the passing of time itself, the steady keeping of it, second after second. And they connect us to a deeper understanding of the eons: A premium Swiss piece is designed to outlive its owner, to bear witness to the lives and benchmarks of generations.

But first, a timepiece must begin its life. If you are shopping for a watch in hopes of starting a new tradition — you’ll own it, then your kids, then your grandkids, on down the line — there’s much to consider, according to Isabella Proia, a specialist at the acclaimed Phillips auction house on Park Avenue in New York City.

The first thing to ask yourself is: Do you want something new or pre-owned? Pre-owned and vintage are in vogue at the moment and have already proven to be ageless. Plus, it can be magical to own an object with history, as long as you consider the realities of an older watch. “Vintage is a little higher maintenance,” Proia explains. “It shouldn’t be over-polished. If the dial is messed up but everything else looks perfect, that’s maybe an indication that something is not right. There shouldn’t be too much wear on the watch, and [you should ensure] it has been serviced well.”

Whether the piece is new or old, she says the trick is to find what you like, then ask the right questions. “Do the research,” she clarifies. “Is it reliable? Is it something that I can wear and my kids could wear? Does it have a timeless appearance? Is it going to look outdated in five years or 10 years? Is it a blue-chip brand?” By blue-chip, she means heavy hitters such as Rolex and Patek Philippe, which are known quantities when it comes to quality.

Audemars Piguet’s brutalist Royal Oak and Cartier’s Tank (worn by Jackie Kennedy, Princess Diana, Cary Grant, and Andy Warhol) have similarly proven their staying power. And there are also possibilities that are more accessible and offer just as much quality and heritage," such as TAG Heuer’s wildly popular Carrera collection, which is celebrating its 60th anniversary this year.

“There’s a reason why people like Picasso paintings — and you know that’s a safe place to put your money. If you are new to watches, then you have some comfort in a big brand. It’s like [blue-chip] stocks that are in the S&P 500 — you don’t have to think about it so much.”