Definitely worth it at $40ish. Just bought a light gray pair off yoox. Didn't realize the sole/roping would be such an ugly color (bright orange), so I had to paint them. Doesn't seem like that should be an issue for you though.
@Caustic Man - I think a white t would really help here. It's not exciting, but it's a pretty simple solution and I think simplicity is a good goal when starting out. Jeans aren't bad, but I agree that they could be worn a little more slouchy and with the cuffing fixed. Boots are nice (and I could imagine them working with a different SWD outfit), but something in black/grey would work better with that jacket. Just a few thoughts, I'm sure others can opine better than...
Looks good from the pics. Agree with IS that the formality is off tie-wise. Have you checked out the Post Imperial ties by Tira? Think something like that (maybe the navy with white squares?) would look great.
I have a ripstop and the high navy twill. Personally, I don't find the ripstop noticeable at all, but if you feel it is, then it might be best to go with the twill. Only downside of the twill, at least on the navy, is that it attracts hair/lint etc. quite easily.