What’s the Best First ‘Big’ Watch to Buy in 2025?

There’s a turning point in every collector’s journey: you’ve owned the Speedy, maybe a few Tudors, perhaps a Cartier or Zenith. But now, you’ve saved up for something more. Not just a nice watch, but the watch. The one that signifies a new chapter.

For many, that means entering five-figure territory. For others, it’s finally pulling the trigger on a dream brand. Whether it’s a hype piece, a vintage gem, or something completely under the radar, the question is the same: how do you decide what to buy?

Start With the “Why”

Before deciding what to buy, consider why you’re buying. Is it going to be your new daily? A grail to keep in the safe? Are you chasing prestige, future value, or personal satisfaction? The best first big watch isn’t the most hyped, it’s the one that fits your goals without giving you buyer’s remorse six months later.

Chris Antzoulis, a watch writer and content creator, said his first big purchase was the Tudor Black Bay 58 Bronze Boutique Edition. “I’d never spent that kind of money on myself before,” he recalled. “If my brother hadn’t been there, I probably wouldn’t have gone through with it.” For him, it was more than a transaction. It came during a period of personal change. “Every now and then, it’s okay to value and celebrate yourself,” he added.

Talking through your decision with someone experienced can help. Justin MacDowell, Watch Specialist at European Watch Company, explained that the first step is understanding the buyer’s lifestyle. “If they’re in shorts and a t-shirt every day, it probably doesn’t make sense to recommend something on the dressy end of the spectrum,” he said. From there, it’s about narrowing the field based on size preferences, design tastes, and desired complications, without making the process feel clinical.

Don’t Fear the “Obvious” Choice

There’s a reason some watches show up on every list. The Royal Oak has become a cliché for a reason. It delivers presence, pedigree, and a sense of arrival. The Rolex Day-Date 36 in yellow gold is another timeless pick. For those with a more modern bent, the Vacheron Constantin Overseas Ultra-Thin remains one of the best-rounded offerings around $25K.

MacDowell said Rolex remains one of the most common choices for first-time high-end buyers. “There are a handful of brands that we see most new buyers gravitating towards—Rolex, Omega, and JLC,” he noted. Still, he emphasized that things are shifting. “Grand Seiko has gained ground in that space, and I think many new buyers see it as a slightly left-of-center way to stand out from the crowd of Datejusts and Seamasters.”

Consider the Road Less Traveled

That said, your first big watch is also an opportunity to define your taste, not just echo what others want. Independent brands can make a powerful statement. A Habring² Chrono-Felix or Ming 37.07 might lack mainstream name recognition, but they offer a more intimate appeal. The Parmigiani Tonda PF Micro-Rotor, for instance, is becoming a cult favorite among those tired of hype.

Looking backward can also be rewarding. Neo-vintage picks like a Lange 1 or an early Breguet Type XX combine history, depth, and daily wearability. Many of these offer strong value below $20K. especially when factoring in craftsmanship and scarcity.

Antzoulis advised staying flexible. “If you’re chasing the ‘perfect’ watch based on a spec sheet or checklist, you’re setting yourself up for disappointment,” he said. “The ones you love most will likely be the ones you never saw coming.”

Understand the Trade-Offs

Every path has its compromises. Buy new, and you’ll pay a premium. Buy vintage, and you’ll have to weigh condition and service history. Go independent, and you may give up resale liquidity. Stick to blue chips, and you risk running into someone wearing the same thing at dinner.

That’s why it’s worth trying on everything you can, exploring options, and talking with others who’ve made the leap. You’ll come away with more confidence in your choice, and maybe even a surprise favorite.

One Last Thing: You Don’t Have to Spend It All

Just because you’ve saved $20K doesn’t mean you need to drop it all at once. Some of the most rewarding watches cost far less, leaving room for a second piece down the road, or a future upgrade. There’s no prize for emptying your budget on a big brand name. The real win is looking at your wrist six months later and still loving what you see.