Everyday Carry has a great post on military styled watches under $100. A cheap watch fan myself, I’m partial to Seikos and own a couple, but I’m intrigued by the Parnis recommended by Ed Jelley.
Parnis Flieger Hand Wound Pilot Watch
This Flieger watch from Parnis is a classically designed pilot watch that has a substantial wrist presence. When legibility is key, the 44mm face and large numerals will come in handy. Featuring a hand-wound movement and a large onion-style crown, this watch is a mechanical masterpiece. The Tianjin Seagull movement is visible through the clear caseback, allowing the wearer to witness the gears in motion. The 22mm dark brown leather strap adds to the vintage aesthetic. At only $85, this watch is a great deal — especially given how much it looks like its more expensive counterparts.