My shoe dilemma

I'm very new to all of this, and have done a fair bit of reading but I still can't wrap my head around shoes and casual wear. I don't own a suit yet, so I generally wear chinos or various wool/cotton trousers (I like the Express "Producer" line, being a poor college student lol), generally with a navy blazer for more formal occasions. I'm trying to find my next shoe and I'm just unsure what to get, they should probably be able to be worn with a navy suit since I will be purchasing one within the next 6 months; as well as chinos/jeans until then. Brown/Burgundy/Oxblood monk strap Brown/Burgundy/Oxblood loafer (tassel/penny/etc..) Brown/Burgundy/Oxblood cap toe Brown/Burgundy/Oxblood wing tip Thanks for any advice! My very humble shoe collection consists of these: Nunn Bush - dark reddish brown. These were purchased before I found this forum Aldo Davis - "Bone" suede, much more gray than the pictures show. Just a bit impractical for all of the rain we get. Banana Republic - Nantucket driving loafer. Soles don't stand up well to much walking, but they were very cheap.

Yea I know! Thats why I need to find my next pair of shoes, I figured I'dpost what I already have. These shoes need to fill a casual/suit gap I guess, since they won't be purely casual nor formal. Thanks for responding though!

Thank you for the suggestions! I guess it's between monk straps and wingtips, kind of my top choices anyways.

I'd like to spend <$185, maybe get lucky and score something in b&s or ebay for even less.