I think a dress watch becomes a requirement at some point.  When?  Well that depends on your style and how often you "dress up".  But there's no rule that says it has to cost an arm and a leg!  My dress watch is a LeCoultre...pre-Jaeger...10K gold filled watch I inherited from my grandfather.  It was worth less than the $100 or so it cost me to get running reliably.  Spend money on watches you'll wear often!  

Now I'm kicking myself for tuning one down!!  This is where my long game approach to watch collecting bites me in the ass.  Excellent review as usually my friend!