How to Find the Right Watch For Your Style (and Wrist)

Here are the different kinds of watches to know—and the sizes that will look best on your arm
How to Find the Right Watch For Your Style
Illustration by Giacomo Bagnara

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With so many watches in the world, from military styles to diving styles to Apple styles, finding one that you're going to want to invest in and wear for years can be hard. But, like any piece of clothing in your wardrobe, fit is paramount to the thing actually looking good. Like, how big is 40mm anyway? And what if you have wrist on the smaller side, or conversely, on the giant side? Luckily, there's a watch out there for everyone. Here's how to grab the one that's fit for you.

Watch people are always talking about millimeters—what do they mean, anyway?
Whenever you see a measurement for millimeters on a watch, it's referring the diameter of the face. Typically, mean's watches fall in the 34mm-50mm range, though there was a period a few years ago where a few companies got a little overzealous and started pushing dish-sized faces up to 60mm in diameter. Personally, we think even if you're an NFL linebacker (or just the size of one), there's no need to ever go over 50mm. Keep in mind that back in the '50s and '60s, most men's watches were smaller than the hulking, attention-grabby ones you may see today, and even today the average guy can mostly bet on looking good in a watch from 34-40mm.

My style is pretty classic—what will look best on me?
If you're the kind of guy that likes to wear clothes that have been in style since the middle of the last century, then your watch should do the same. Any watch that's been around for a few decades, like a Rolex Submariner or Omega Seamaster, is your best bet. In fact, you may even want to pick up a vintage style, which will not only look great, but in many cases will be less expensive than one that's brand new. (Why that's the case is kind of beyond us but it is and we're not going to complain.)

What if I don't have Rolex money?
Shinola and Filson (the makers of your favorite waxed tote bag) both make great mid-century modern-inspired watches for well under a grand—leaving you money to spend on the rest of your wardrobe (which, yes, is still very important).

Okay, so I'm kind of into capital-F Fashion. Are there watches out there for me?
If picking up the latest runway trends is more your speed, you may want to pick up a few, less expensive watches that you can pair with your looks no matter which way the wind blows on any particular day. Something with a distressed black leather band is the perfect match for a pair of waxed jeans and Chelsea boots. A watch that leans a little more futuristic (without going full-on performance) is what's going to look best with your freshest pair of hi-top sneakers and graphic tees. And if you're big in the fashion game, why not get a watch from one of the world's best designer labels?

What's the best kind of athleisure watch?
Certainly there's an argument for ditching the watch altogether in favor of one of those step-tracking wristbands if you're someone who's looking to hit some serious fitness goals, but then again, those tend to look terrible whenever you're not wearing head-to-toe spandex. So, though it may seem slightly obvious, the Apple Watch is the best option out there for performance and style. If you tend to wear a lot of tailored sweatpants, the rubber wristband should do just fine, but if you're feeling particularly fancy, spring for the Hermes watch strap for those special occasions. Just make sure to pick up the right size for your wrist.

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