Okay, trivia time.

[T Bone]

What watchmaker made arguably the first "pilot's" watch, and what famous aviator was it made for?

I will post what I believe to be the correct answer (I'm pretty sure on this one), after we've had a few responses.

[Nokie]

I will try the first part of your question-

Longines Weems?

Not sure about the second part, but maybe Charles Lindberg?

[Matt]

Well, there's the Howard pocket watch carried by Orville Wright...

But failing that, there's Arthur Brown's wristwatch, as used for navigation on their 1919 non stop atlantic crossing? It is directly referred to by him at several points, but I have never worked out what it was - I'd love to know. Presumably some sort of trench watch.

[tribe125]

It depends whether you mean watch carried by pilot or watch for pilot...

Cartier. Santos-Dumont.

[Samanator]

It depends whether you mean watch carried by pilot or watch for pilot...

Cartier. Santos-Dumont.

I believe this is correct.

[M. Montaigne]

What watch did the Wright Brothers wear?

[Matt]

They had two. A Howard pocket watch and a stopwatch. The pocket watch was carried, but I agree that the Cartier is a true wrist watch. However, pocket watches were serious products for pilots up to WWII as the profusion of flight certified RAF pocket watches demonstrates.
So it all gets a bit semantic... That said I think the Cartier, by the spirit of the question.

[Nokie]

All good guesses, so I can't wait to see what the correct answers are.

Never thought back far enough to consider the Wright Bros, nice call.

[T Bone]

It depends whether you mean watch carried by pilot or watch for pilot...

Cartier. Santos-Dumont.

Correct! Santos Dumont asked Cartier (his freind) to fashion a watch (pocket watch) onto a strap of leather so that he could wear it for use in his flying endeavors. Cartier still maintains (in name anyway) a reference to that connection with a watch named for the famed aviator.

[tribe125]

If you need my address for the Cartier Santos prize, just drop me a line.