So, I am in the fortunate position to be able to get a few new items in the coming weeks. I bought some Frye Chelsea boots and I returned them because the back heel was too big for my liking and the front was too rounded and elevated. I wanted that something that was rounded in the front, not square or anything of the sort, but something more subtle and not so elevated. I am now re-thinking my buying boots at all. I am in college. I am deciding between a pair of Puma Speedcat US version, Nike Dunks, J Crew Milbrook driving mocs, boots, which I can't seem to find any I like, or two American Apparel hoodies. I can get two of those items. Let me explain my rationale before you go presuming I have horrible taste. I like the white and black US version Puma Speedcats. They are a nice flat shoe and they are versatile. I can wear them every day and I can wear them to a party too and not feel odd in a college campus. I love Nike Dunk lows. I can wear them every day and I can wear to them clubs and bars, most of the time, but they define the outfit and I can't wear them with a nice button down. It seems too odd. With Dunks, I feel like you have to stick to a very certain style, so in that way, they aren't as versatile. J Crew Milbrook driving mocs are nice and most importantly, they serve as the formal shoe for college kids here at Penn. I know you aren't supposed to wear them outside of summer and spring, but kids wear them year round here and they are very good for pulling off the button down and jeans look. They can also be worn with a t-shirt and jeans, but I would not want to wear them every day because despite what they are actually meant to be used for, it would be too formal for class. Boots would be nice, but first and foremost, I can find a freaking pair I like. The ones I want are too expensive. Also, while boots are probably the most durable and every day shoe, I would feel weird wearing them every day here at Penn because I don't know many, if any at all, who have boots or more over, wear them often. I have no American Apparel hoodies and I love to wear hoodies, jeans and a t-shirt because it is so comfortable. I truly feel like the Pumas are probably the most versatile shoe considering where I am in life and all, but I am interested to see what you all have to say and if you have any other suggestions. THanks so much for the advice.