I had a collection of just a few pairs of shoes that I wore for business and casual for many years. Black cap toe oxford Brown cap toe oxford Brown loafer I had boat shoes and sneakers for very casual Get quality over quantity and make sure they fit. Most shoes salesmen will put you into anything and send you on your way. Shoe fit varies by maker and so you may need a different size depending upon the brand. Go shopping later in the day because feet swell a bit. Try on a size larger and smaller. Insist upon it. Maybe you need a wider shoe? When going for a good fit make sure your heal fits comfortably (don't let it slop around. If so try a different shoe) and then have plenty of room to wiggle your toes. If not, then try a wider or larger size. Or you may need to try a different shoe all together. I have brands that I just can't get to fit comfortably. You may not like to shop for shoes but there is no reason not to be comfortable in something you must wear every day. There are far too many good options out there to not be comfortable.