"It's better to have one good pair of shoes than a half dozen cheap ones, because the cheap ones look cheap even when they're new, but the new ones look good even when they're old. Quality by definition is the best you can get for your money. If you buy a pair of shoes for $500 and they last you 10 years, that's $50 per year. If you buy a pair for $100 and they last you six months, which was the more expensive? I think the Old Money WASP guys were just cheap, so they always bought the best". Yup Exactly. If you buy a $500 pair of shoes that last you 10 years, that's $50 a year to wear a great pair of shoes year in and year out. Alternatively, you could spend the same amount (or more) every year on crappy shoes and wear a crappy pair of shoes year in and year out.