Yeah, I'm totally the nostalgia type too, I'm actually surprised I like something from the later series more than the older series. His original outfit I of course feel the most familiar and fond of, but in terms of style, I like the hoodie much more, it's more natural looking, yet it maintains a unique style that suits him. It also makes him look a little more built, he looked pretty skinny in the loose vest. His Sinnoh outfit isn't as good, though the baggy jeans would have suited his Hoenn hoody really well. The Best Wishes outfit is ok I guess, though I don't really like his re-design, he looks younger than he did when he started out in Kanto.
I never really got used to Misty leaving the show, which is the primary reason I havn't watched much of the newer series. Sure, she'd been around for a long time and I can see some people wanting a change, but she'd been around for so long she felt like an important part of the show for me. They handled the goodbye pretty well though, I always liked how they didn't go over the top with the romance like many other anime movies/shows do (afterall, they're only around 10-11 years old), but they did recognize a special friendship between Ash and Misty.