like the Yacht-Master and some versions of the Daytona. Nearly all of Richard Mille’s watches come on rubber. These are pieces designed to endure the elements, whether that means taking the Yacht-Master out into the actual sea where it may be splashed with salt water, or playing tennis with a rubber-strapped Richard Mille on.

Rolex is so strict about its strap/bracelet pairings that companies have sprung up to circumnavigate the sanctioned rulings. Those deadset on customization can turn to Rubber B, which makes rubber straps that fit on different Rolex watches.

NATO straps 

The NATO strap, which was designed in 1973 for members of the British Ministry of Defence, is an inexpensive, durable, and often colorful addition to a watch. Everything that made it a great strap for those going into combat makes it a good option for civilians, too.

The way the strap attaches to the watch by looping through both spring bars (the pieces that keep a strap attached to a watch) pays immediate dividends. First, it keeps the metal of the watch from rubbing against your skin and is designed to sit snugly on the wrist without much movement. Second, because the strap goes through both spring bars, if one breaks, the watch won’t go flying off your wrist.

Bund straps

The bund strap is a fat leather pad with loops that your watch inserts into—think of it the same way you might a case for your iPhone. The style’s origins are odious, though: it was first issued to members of the air force fighting for the Federal Republic of Germany (known as Bundesrepublik, hence its name) in WWII. The pad was designed to keep metal made uncomfortable from flying through very hot or very cold conditions from touching the skin directly. But the strap came back into style in the ‘70s for purely aesthetic purposes. Paul Newman loved a bund strap, as did Steve McQueen and Robert Redford, making it a swaggering, super-masculine choice. Be warned, though: it’s also an extremely polarizing option that inspires strong feelings both for and against.

So Where Do I Actually Buy a Watch?

Purchasing many of the watches covered here—particularly those that can be had for a few thousand dollars and under—can be as easy as hitting Add to Cart. Hodinkee has turned itself from watch blog into watch shop, stocking new arrivals and best sellers from big and small brands alike, a grip of slick vintage options, and a reliable drip of its own coveted limited edition collaborations with the likes of John Mayer. Tourneau and Wempe are ever-reliable options, as is Watches of Switzerland.

But it’s always worth it to head to a multi-brand watch store, or an authorized dealer for your brand of choice, in person. That’s because you’ll want to try on whatever you’re buying—and because you can’t just log onto Rolex.com and opt for two-day shipping.

One thing you’ll learn as your tastes begin to run toward the luxury watches of the world (we’re sorry; this is definitely going to happen) is that buying gets a touch more complicated. Basically: when it comes to the most popular watches for men on earth—your Rolexes and Pateks and APs—scarcity is the name of the game. Dealers only receive so many pieces from a new release, and they have to decide which loyal customers will get the opportunity to buy one. Which means that, if you want to work your way up to buying the big boys, you should start now: find a dealer you like, and buy with him or her as you build your watch collection. That way, when that bonus check clears, you can stroll on down to the shop (or fly to New York) for pick up secure in the knowledge that a higher power (a watch dealer with ready access to Submariners, say) is looking over you.

One Essential Tip for Finding a Killer Vintage Watch

Maybe you just want your Royal Oak now. Or maybe you want a LeCoultre Reverso that’s picked up a few character-adding dings on its reversible face. Or maybe you want a Rolex, but don’t quite have new-Rolex money. Lucky you: the vintage watch market is frothier than it’s ever been. And if you’re the kind of person who loves raw denim for the way it breaks in, or doesn’t trust a wallet until it’s good and broken in, you’re going to want to go vintage.