I apologize in advance if I should not be creating a new thread for these questions, but here goes: While most of my wardrobe consists of items most appropriate in the "streetwear and denim" forum, I would like to purchase a first pair of dress shoes and am looking for suggestions from forum members. The shoes will be worn with a charcoal gray TaT suit, as well as more casually with jeans and other pants. I'm thinking of getting a dark brown captoe balmoral with some light brogueing, though I like derby/blucher styles too. I don't want too conservative a shoe, as I am young and won't be wearing them to the office on a regular basis (my office has a very casual dress code). Furthermore (if possible), I would like the shoes to be formal enough that they are appropriate for wear at a non-black tie wedding (worn with a charcoal gray or navy blue suit), yet casual enough to wear with jeans or slim trousers, a slim button down (eg. BoO) and a bedford or norfolk style jacket (a la engineered garments). I am young (22), and my wardrobe generally tends towards a slim/fitted look, but not as extreme as some on the streetwear and denim forum. If possible, I would like to spend less than $300. To complicate matters, I live in Toronto, Canada - where good men's shoes are notoriously hard to find at a reasonable price! I've been looking at Allen Edmonds, and plan to go to Harry Rosen to try on a few models, but would like to consider options outside AE too. Any suggestions with the above in mind? Thanks in advance.