Suede desert boots are almost always a good move. They're versatile–dressy but not too dressy, casual but not too casual. You can wear them on a date, to the baseball game, wherever, whenever.
The only problem? Nearly every guy you know (and their brother) has a pair. If you want to swerve in a different direction, consider these suede derby shoes from minimal footwear pros Common Projects.
Branded with the same gold-stamped serial numbers featured on their sneakers, these made-in-Italy shoes will handle anything a desert boot can, just in a more elevated way. A "faultless choice for smart-casual occasions," the product description reads.
The $530 price tag might be a tad steep–but considering the quality of construction and the fact you'll have these for years and years and years–it'll be money well spent.