Ok, please bare with me I'm sure these questions have been asked before, i have used the search, just looking for a little more specific answers. I recently moved to NYC and am planning on redoing my wardrobe in attempt to shed my old clothes from college to something more mature. Any advice at all would be real helpful. I'm not 100% sure what my style is but I'd say pretty a pretty casual type street wear. Something similar to the pictures below. /\ I like other color jeans / darker denim as well but these were the best pics i could find My budget is about $700 to get started. So far I have 2 jackets I like, one pea-coat type jacket and a bomber type jacket I also have some Levi 511's which I've grown to like a lot so things that match these well. In order to pull off a similar general style as those in the pictures, what are some essentials I should look into purchasing and what stores would you recommend that won't clear my wallet to fast? I'm looking for new shoes, button-ups, and whatever other essentials you would recommend. For shoes I was thinking something like this? But i'd like to see more of a selection if there are any good shoe stores on the inexpensive side. (I'd rather not spend more than $150) http://comfortshoevillage.com/mens-shoes/clarks-originals-desert-boot-black-suede.html Also, if someone could throw out some names of NYC stores which have quality button up's that would be a big help. Currently I've been mainly going to Express and H&M. H&M shirts seem to shrink a lot after washing though. Thanks!