I posted a week or two ago about starting a new job and needing some real suits (as opposed to the JAB stuff I had), and got some great responses. Now, I need to add a real pair of shoes to these suits. The new job is with a financial firm in CT where I will be wearing a suit daily and be client facing some days. It's definitely a little bit more conservative locale (think country clubs and hedge funds), but I want to look good and have the shoes add to my look. I also to be able to own these for a long time, and I aim to be living in NYC sooner than later. I currently have a pair of basic black J&M - http://images.johnstonmurphy.com/images/products/1_52950_FS.JPG - and a pair of CH burgundy penny loafers - http://www.peltzshoes.com/resize/ResizeImg.aspx?img=/images/vendors/COH/03504/03504.jpg&height=360 Ideally, I would like to keep cost under $250, so I reached out to AE to get their list of seconds/discontinued, and I'm going to their store later to get my size. Any thoughts in general on the type of shoe to get next would be very helpful. If AE seconds aren't the way to go, by all means let me know. I'm sort of leaning towards a dark brown wingtip, but open to a lot. I like the look of Monks, but don't know if I'm ready for that with my first real shoe. Cap vs. Wingtip? Oxford vs. Monk? Dark brown vs. light brown? etc etc etc For the suits I ended up getting up a Suitsupply Napoli charcoal suit, and two BB Fitzgerald suits, one in navy (summer weight) and one in navy stripes. I also have a a similar navy light striped Macy's suit, and will occasionally be wearing chinos and a navy blue blazer. Thanks, it's a long post, I know, I appreciate the feedback (I seem to get more and more confused the more threads I read).