Vintage aviation is cool. The pilots back in the 40's looked cool and I know that wasn't the intent, but still that look is timeless and countless modern day brands have tried to capitalize on it. I've bought into it and if you Google military watch or pilot's watch, the results are endless. Who hasn't fallen down that wormhole a few times?
Fossil back in 1988 came out with the Retro-Pilot series of watches. This could very much be one of the first collections or series of watches they created. Due to the age of these watches or possibly lower production numbers they are not common - I've only seen several watches show up online in recent years. The watches I have don't even have model numbers or years on the back, but they did have model numbers and I've included them below with the images. In total there were 22 watches featured in this collection and they ranged from Paratrooper, Navy Diver and various pilot themed watches all with leather bands.
A few details is that the cases on the 2 I've had both measured 37MM, which is really small. The bands were 18MM and embossed on the leather band is Fossil Air.
Rumor has it Fossil is soon to return to these roots with a Vintage Aviation Series in 2015. Regardless enjoy the several watches I've found. I wouldn't categorize them all as pilot watches, but they are "distinct and unconventional as those daring aviators that inspired them".