Notice that the word “should” is in quotes. We should all be so lucky to own one or two watches that we really like in our lifetime. Some guys don’t even like wearing a watch, and plenty rely on their mobile phone. But many of us do like using a watch to tell the time, and c’mon, it also looks good on your wrist.
Before we get to the aesthetic styling of each watch, you’ll want to keep in mind three key factors in how the watch is constructed when purchasing a timepiece:
Sierra Trading Post has a terrific watch buying guide, so go there if you want to read up more on that stuff. Onto the styles. Building a watch collection around these four should ensure you always have an option for your wrist.
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If you’re going to buy only one watch, this classic dive style is probably the one to get. There’s no leather that requires matching with your belt and shoes, and as long as it doesn’t get too aggressive, you can pull it off with a suit for less formal occasions. But be aware. Plenty of these look too much like man-jewelery. Keep the shine on the links to a minimum, and know that as the links get smaller and more intricate, it starts to look more and more like a bracelet instead of a watch. You want some toughness in there. Suggestions:
Sure the male style community now favors brown leather dress shoes. But plenty of us default to black when we dress up. Well shined black shoes with a grey suit has a sharp, utilitarian, anti-dandy feel. Look for a silver or black dial chronograph to match. Steer clear of chunky rotating bezels which, when combined with the chrono, makes it too casual. A chrono alone makes it easier to dress down with a sweater and jeans. Suggestions:
Look for dials that are either black, cream, silver, or white. Blue works great too. Many brown strap watches come with a matching brown dial. That’s a ton of brown and it can look a little too much like a couch from the 1970s. Black and brown can in fact go together in certain instances. Timepieces and beer are two examples. Suggestions:
The funny thing about a rubber strap is that it’ll often look fine with any belt/shoes combination. Brown boots, black watch strap? Sure. Along with your stainless steel watch, you shouldn’t have any problems getting this one wet, dirty, and more or less beating it to death. Suggestions:
Should a canvas strap Timex Weekender style have been included? What about a plain and simple dress watch? Agreements, disagreements, and other suggestions should go below.
A note on buying online: There’s plenty of sketchy watch sellers out there on the net. If you’re buying off Amazon, make sure to either buy direct from Amazon, or, look for the word “fulfilled” by Amazon. That way, Amazon has skin in the game in case you get a dud. All links to Amazon were created to point to Direct or Fulfilled by Amazon watches, but know Amazon automatically switches to 3rd party retailers when available if a watch sells out.
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