Rollies and Pasha's They Drove Me Crazy: A Guide To Watches
Ever since I was a little kid I aspired to own a wristwatch. I felt that it was a stepping stone on my way to dressing like a gentleman. I felt having a watch meant not only that I could tell pretty ladies the time if they asked me, but it also looked good. I was obsessive and would force my mom to stop at every watch store in the mall. Gleaming at watches way out of her price range, with eyes as wide as Disney characters, I wished.
The first watch I remember getting (besides the Mickey Mouse one where the arms told the time which was fresh at 6 years old!) was a clear swatch with multicolored numbers and a black face. It was the 90's and it was a sick watch to have for a kid of 10. It came in a plastic case (the whole thing was made of plastic) and when I wasn't wearing it, in the case it went. I loved that watch until the strap broke and that was it, time to move on.
My next purchase was a Victorinox Swiss Army steel link band with a blue face and the date. This was a big purchase for me, I had saved up money and was in Canada visiting family and made the leap (at that time the exchange rate was still highly favorable to the American dollar). I wore the shit out of this watch, oh and it too had a case, one of those fancy ones that flip open. It slept there every night, until I lost it that is.Â
Now that I am grown I have been curating a watch collection of my own, leather straps, day & dates, web straps, the options are endless and so are the makers. Let's take a look at some of the high end classics.
If you happen to have $40,000 or more lying around I.W.C. makes some beautiful watches, like the Da Vinci Perpetual, and has been for centuries. These are super luxe and are stunning to look at when you step out of your Bentley and onto the red carpet. It's a lifelong investment that will last beyond you, if you care about that sort of thing.
Okay so you've got money but, not "Jay-Z" money. So maybe you want a Rolex. Classic choice. Ranging from $4,000-as much as an I.W.C. you can find a model that fits your budget. I love the Submariner with the date. Silver with a black face, it's sharp and works with almost anything. Once again the craftsmanship here is amazing and this thing can go underwater bitch. Biggie said it best, "Put your Rollie in the sky and wave it side to side". I've dreamed of owning one ever since my boss at my first job flossed one. (Blue face, date, steel band)
Not a Rolex man, how bought Breitling? For the aviator in you (or her) they also make some well crafted form & function watches. With a slightly higher price tag than Rolex ($6-7,000) they've been making chronograph timepieces since 1884. So history is on your side here, once again beautiful and stunning, a piece that will last a lifetime. I like the Navitimer with a black face and brown leather strap when I'm flying my ICON A5.
So your not ballin' like that yet (always ask for layaway ain't no shame in that) but you still want style and something that's gonna hold up. My good friends at Victorinox make great pieces. They start from about $500 and go up to $1,650 and they look great. Don't expect to get any gold chain link here but you'll have people appreciating your wrist. The Maverick and Officers styles are great and they do Chronograph. When I'm screaming order at superior officers I like the Air Boss Automatic Power Gauge with a white face and brown strap, it says I have authority but also good taste.
 Still stuck paying your student loans, Kenneth Cole (see more here) makes some stylish watches for men starting from $95 and going up to $250. They have all the up to date trends and I had a watch from them that lasted for 4 years. Your broke ass still wants to look good? Check out Timex, they're doing a great job at trying to make something affordable and still look good. It won't shine like a Breitling but it will most definitely last and they start at $38 and go to mid $200's.
Lastly, don't let your wrist go naked now that you've got yourself a suit or two in the closet, just because your phone tells time doesn't mean you should rely on it.