Editor?s Note: In this edition of the 3 Watch Collection for $5,000, reader (and newest contributor) Brett Braley brings us a refreshing collection that skews the expected in creative ways. All three of these watches bring a unique personality to the table, and offer a surprisingly diverse range when considered together.
If you?d like to submit your own 3 watch collection for $5,000 can you do so at the form right here. 
I have always hovered at the periphery of watches. Whether it was the Fossil watch I got for graduation from my parents or the souvenir Mickey Mouse watch I begged my aunt at Disney World, I have always seen watches as the supreme accessory for looking put together (or, at the very least, faking it). 
Recently, I have stopped being at the periphery of watches and have found myself smack-dab in the middle of the hobby. A few weeks ago, I attended the San Francisco Wind Up as a representative of my company, Esterbrook Pen Co. I?m the Director of Digital Marketing for a company that specializes in luxury pens. While this is a niche industry, it?s not any more niche than, say, watches and the two circles of the Venn diagram seem to be overlapping a good bit. When tasked to pick three watches, I went with the same criteria I use when picking a good writing utensil: value, aesthetic, and quality. I want something that will last, look good, and be worth the money I?m paying. And, last but not least, I wanted to go with three brands which aren?t as well known...