Surprised no one has mentioned Etnies Marana or Joslin 1 yet. Easily, two of the best current cupsoles. Comfortable, durable, they look great (at least I think so) and skate great!
Marana Mid is another option but those are so hard to find now. Doesn't seem like they're keeping them in production as frequently as the regular Marana.
Will also vouch for these:
- Kalis S and Legacy Slim, but do an insole swap on both of those shoes. Stock DC insoles are garbage most of the time.
- Proper Rook or Cinex, not Conquista, though. Too narrow in the toe for me personally and the heel look isn't as good as the other two from them.
- Emerica Alcove CC, Gamma, Spanky G6 (only if you like super thin uppers though)
- Es Quattro, Evant, Accel Slim Plus (stock insole or swap)
- NB# 1010, 440 (low and hi)
- Adidas Tyshawn, Copa Nationale
- Nike SB Dunks (but we know how difficult these are to get right now...)