#2. Adidas Rom Shoes ($75 @ Amazon.com)
This Adidas shoe made its debut in the 1950s as an all-around trainer; it’s kept the distinct look but has been reworked to work for casual wear as well as training. While you might be focused on its function over its fashion, the Rom’s waxed suede, leather upper, and running-inspired outsole can easily lead people to believe style was the selling point.
#3. TOMS Khaki Men’s Canvas Desert Oxfords ($45 @ Amazon.com)
Buy a pair or shoes from TOMS and you can brag to women about how nice of a guy you are: TOMS gives away a pair of new shoes for every pair purchased. Okay, so you probably won’t brag about that (we hope), but these vintage-looking, heavily stitched canvas sneakers will deliver superior durability and, thanks to stealthily placed elastic straps, a super-snug fit.