Definitely can do it, but even though you can wear loafers all year, I normally wear them spring summer exclusively. With that said, you could definitely wear them with shorts, but I feel like a natty CXL is better suited for that and leave the calf to the chino's, dark denim, and slacks lolI am as casual as it gets but I definitely enjoy calf with tshirt/denim, just because. Tobacco looks fantastic, just enough mahogany/red to make it interesting. I still don't have a plain medium/dark brown shoe, always gravitated towards oxbloods/chili or tans/naturals. This tone on a ptb or cap toe boot would be sick if they never do a merlot/burgundy tone.