Thinking no at this time. I have the stainless steel with milanese currently. Looking at all the options for the new watch, the stainless is still the most appealing to me, and the milanese looks like my band of choice still to this day (I really like that band). I'd probably just buy a new band, because I'd want to sell the original watch with the milanese I have now and get a new shiny one for the new watch.
The new watch is over $800 with Apple Care and taxes, and it looks like on e-Bay I would net (after fees) probably around $300 for my current watch.
Even though I can afford it, that's a lot of dough for the water proofing and faster processor and GPS, and I'm not sure my usage patterns for the watch would be any different than what I have now (steps, notifications, time, maps, etc.). GPS is nice, but I always have my phone with me.
I guess we'll see if Watch OS 3 alters those usage patterns and incentives and upgrade.