For sneakers go for something classic and timeless looking. Look up Adidas Stan Smith. Those should run you about $120.
If you're going the loafer route, unfortunately with dressier leather shoes, generally you get what you pay for. If you're going the Aldo or Steve Madden route, just wear a pair of Stan Smiths instead. If you're serious about getting nice loafers, go to O'Connor's or Harry Rosen and let them guide you. contrary to popular belief, for your first pair, DO NOT buy black shoes. Go with a nice dark brown with minimal red or yellow in the colour. Be prepared to pay about $400+ for them though. Oh and don't forget the matching leather belt. If you take care of your shoes, however, they'll potentially last a life time.
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