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Loafers
driving mocs or a loafer would be a better choice IMHO
Desert boots
Boat shoes only for summer fridays in the office
Don’t wear boat shoes, you’re not a fraternity brother
Driving Mocs for life
Cole Haan’s Zerøgrand line are great for this IMO, comfort and they can be dressed up (leather variations) or down (knitted, more of a sneaker look)
Both great choices with chinos / jeans
Quoddy bluchers
I’d stick with dress shoes, outside of SF I can’t imagine a scenario where someone will think less of you for wearing Allen Edmonds. But if you really want to I’d suggest Chelsea boots.
Monk straps
Boat shoes are never out of style. But always too casual.
Second on the desert boots. Just got a pair of those suede ones from j crew for 40% off