5 Must Have Watches, Around $5,000 | OMEGA, Rolex, NOMOS

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Which luxury watches are actually worth the money? From the Tudor Black Bay 58 and OMEGA Seamaster to the Rolex Datejust and Cartier Santos, these are the watches I’d consider if I were starting my watch collection again.

Spending more on a watch doesn’t necessarily mean you’ll enjoy it more. So what makes a luxury watch worth buying—and, more importantly, worth wearing? I’m breaking it down into five categories: the elevated everyday watch, the dress watch you’ll actually wear, the beautifully made tool watch, the connoisseur’s choice, and the icon you’ve always wanted.

We’re talking comfort, design, finishing, mechanical interest and the emotional side of watch collecting. Sometimes the sensible choice is a Tudor. Sometimes Grand Seiko gives you the details you didn’t know you cared about. And sometimes you’ve wanted a Rolex for twenty years, and a different black dive watch simply won’t scratch that itch.

Watches discussed include:
• OMEGA Seamaster Aqua Terra 38mm and Seamaster Diver 300M
• Rolex Oyster Perpetual, Datejust 36, Explorer and Submariner
• Cartier Santos
• Tudor Black Bay 58 and Black Bay Monochrome
• Longines Conquest Heritage
• Grand Seiko SBGM221 GMT and Shunbun SBGA413
• IWC Pilot’s Watch Mark XX
• NOMOS Club Sport Neomatik Worldtimer
• Jaeger-LeCoultre Reverso
• Breitling Navitimer

Whether you’re buying your first luxury watch or adding to an established collection, these are five ways to find something that earns its place on your wrist.

Which luxury watch has been worth every penny for you? And which would you choose if you were starting again? Let me know in the comments.

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