Hey Tyler, I am a big shoe person and it is definitely something I notice on a guy, so I thought I would give it a go. I think chukkas, brogues, wingtip and casual oxfords are nice, but it is hard to say without seeing the clothes and a sense of your style. But just to give you some ideas, here are a few to look up that I think look nice, hip, but not overly dressy. You sound like you like things more casual(note some are pricey, but I an sure you can find something similar a lot less expensive. I just pick a few online that I thought looked nice)...
Cole Haan Zerogrand Wing Ox Frye Justin lowlace Oliberte Navivo Born Sandor Born Jax Anhu Roanoke
My H hated to shop, so he was happy when I went out and bought him clothes and shoes. Everyone always thought he looked nice, so I am fairly confident in this area!!
Me: 42 H: 40 M: 12 H moved out - 8/2015 I filed - 8/2015
