This is about as modern as we go with watches, but given how cool this one was I just couldn't resist.  
 
This is a fully operational, time-accurate famed Benrus calendar date watch.  It takes a few minutes to get used to how it operates everything, but once you get the hang of it... tons of fun to wear.  Add on that killer nato strap and you have yourself a classic looking timekeeper that carries the edge over your other vintage watch buddies.