To a certain extent. You shouldn't overdress, because you'll look stupid to either gender. But you shouldn't sandbag yourself, either. If you're wearing nice,

To a certain extent. You shouldn't overdress, because you'll look stupid to either gender. But you shouldn't sandbag yourself, either. If you're wearing nice, dressy or semi-dressy clothes, a pair of casual shoes will look silly. And if you're wearing nice, casual clothes but cheap sneakers, that will look almost as silly. You're doing yourself a disservice if you wear a fitted RL polo, nice fitted raw jeans, and whatever pair of Adidas was on sale. You'll be making a fashion statement, and that statement will be "one of these things is not like the others". Plus, a "real" leather shoe, like the OP talks about, can last one or multiple decades, if they are resolable and of good quality. In certain styles, you actually save money by buying more expensive shoes.