I am a pilot.
I am a horologist, as well as a stylophile (so is another member here)...
A VERY nice (my USAF blood is about to burn) watch IS the Citizen Blue Angels watch. I have the original, and the follow-on. SUPERB timepieces. I don't normally wear it in the cockpit of a tactical aircraft. A flying bus is fine. The price point is excellent.
Hamilton...well known for aviator watches; my first USAF-issued watch, complete with radioactive "glow in the dark" parts, was a Hamilton. They have many selections...all very nice.
If you have no budget...the Rolex Air-King is synonymous with aviation history. It's also very basic and pricey! The above watches are WAAAAAAY lower in cost and have more functionality. Of course, at the bar, nobody talks about (using their hands) "There I was, shooting down my Citizen..." It's ALWAYS "there I was, shooting down my Rolex..."
And lastly...for the "I have a budget but it's healthy..." there is Omega's Moonwatch Professional. It has it all and is VERY nice. It's also pretty rugged.
Okay...that's the "cool" factor. Now, what would I wear flying and into whatever I got into? I've worn my Citizen when flying large aircraft. I've never worn any of my high-end watches. My dad wore his Omega when he flew. Today I'd wear the Citizen or I might get a Timex MK1 Chronograph. It looks pretty excellent.
Oh...I have worn my USAFA branded Tag... it's pretty rugged.
Okay...I should NEVER have read this thread....