In the 136th episode of 40 and 20, The Watch Clicker Podcast, we break from our tradition of strictly affordable watches and explore the world of the sub $1000. Specifically the best dress-sport watch under $1,000. Let us know if we missed one of your picks and feel free to message us with your scores, now that you have the rubric. 
Our Top 5 (in no particular order): 
Seiko Alpinist available at gnomon
Orion Hellcat
Christopher Ward C63 Sealander
Astor + Banks Fortitude
Traska Summiteer
Other Things: 
Andrew:
Whisps cheese crisps: whisps.com 
Everett: Platypus bladders: platy.com
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Intro/Outro Music:
Bummin on Tremelo, by Kevin MacLeod (incompetch.com)
Licensed under Creative Commons: By Attribution 3.0 License
Creativecommons.org/licenses/by.3.0/