CalmDC redoes his wardrobe - criticism is still welcome

Doing a complete revamp of my casual wardrobe.  Won't post any picks at this point, because it's all getting chucked.  Think of it like this - the best piece of fall/winter clothing I own are Levi 501 Raws... everything else is downhill from there.

Recent Purchases:

Tops:

Nothing

Bottoms:

Unbranded Indigo Tapered - Arriving 10/06

Tried buying at 7th Street DC Urban Outfitters, but the store clerk looked at me cross-eyed when I asked him if they had any in stock.  Purchased online - will post pictures of the fit when they arrive tomorrow.

Shoes:

Sperry Top-Sider Halyard Chukkas - Canvas Brown - purchased last Sunday

Kind of regretting this purchase now, but they were cheap... : )

Clarks DB Beeswax - Arriving 10/06

Clarks DB Grey Leather - Arriving 10/06

I know that the recent purchases thread is out there, but I want to keep everything organized in one place over the next couple of months.  Completely open - rip into anything I buy/anything I post that doesn't fit or look right.  Comments, recommendations, &c also appreciated.

Received both orders a couple of minutes ago.  Clarks look and fit great - extremely impressed. 

The Unbranded Tapered in 34s... great quality, but the things are too small at the waist - although they seem spot on for the thighs, knees, & a little too large at the ankles.  I normally wear 33s, so this is a little... distressing?  

Will have pics up later today. 

Edit: Also, the grey leather Clarks are crazy.  Going to look great once they're broken in.

Edit

Getting constructive guys, if there's something I'm missing - and there obviously is - point me in the right direction.  Search brings up a lot of subjective opinions, but would much appreciate it if someone could - at least - point me towards reasonably objective criteria that I can use to measure basic things like 'fit' against.  

@okay.w0w: I get it.  The question isn't whether sanforized denim will stretch - I know that it's not going to - but whether it's okay for it to be tight at the waist.  I can still button it up and it's not uncomfortable once it's on.  Where do you draw the line between tight and too tight?

Heh, I'll make this my last post before putting this thread to rest 

@Froosh & Taco - thanks for the advice.  I'm sizing up one and switching from tailored to straight legs.  I don't want to switch to another brand (APC Rescues are my fall back) because... I'm cheap. 

@polarcream - love them squats