Yeah - it is a polos and chinos environment. Sorry I didn't make that clear.
Do you think that grey strap will go with it well?
I have seen a few posts recommending Land's End and I had been eyeing it a bit. It looks like their charcoal wool pants are on sale right now for right about $80. I don't necessarily need them right away but probably in 1.5-2 months, do you think I should go ahead and pull the trigger for that or is it in my best interest to wait for a better sale within that time frame?
Lands' End has a 30% off sale at least once a month. You should probably wait, especially if you don't need them so urgently.
I only go to BR if I can't find the item that I want at Lands' End, Brooks Brothers, Club Monaco, or even J Crew. That said, I have been going to BR a lot lately because quality seems to be trending up. Also, considering OP's need, BR may well be one of the best choices for him because it offers the right fit, styling, and accessibility for a slim college guy.
The small check is great, the dots are pretty good, the thick stripe is somewhat questionable. I think you are getting the idea great by youtself.
Can alterations fix this: lapels bow out, belly stretches forward, diagonal wrinkles on shoulder, vertical wrinkles on back (photos below)? How hard/expensive is it to fix? The issue occurs with all OTR suits for which the shoulder width fits (tried dozens). If I hunch my shoulders forward, the problem mostly goes away.