I own the plain toe version of this. First off, if you have narrow bottom trousers, these might look a bit heavy. However, if you trouser bottoms are 18" and wider (typical dress pant width), they'll be fine. I wear them with: Jeans, wool flannel (both odd pants and suits in 3 season weight and heavier, so long as there is some visual texture), cords, heavier cotton pants. They are a perfect shoe. I'm still wondering what role they will play in my wardrobe during the summer, but that's not a big concern. If you get them for $325 or under, it's a steal.