Buy it once.

Can it be repaired, resoled or re-waxed?A cobbler, a tailor or the maker should be able to fix it when it wears.

Is it made of wool, cotton, linen, leather, steel or wood?Natural materials age well, while most plastics and synthetics only get worse.

Has the maker been making this same thing for twenty years or more?A company that keeps making one thing has usually worked out how to make it well.

Will you use it at least once a week?The things you use every day deserve the money, and the rest do not.

Does it come with a long warranty or a repair program?A maker who promises to fix it is telling you how long it should last.

Is it plain enough to look right in ten years?Logos, trend colors and novelty details date faster than anything else.

Will it cost less than a dollar a wear over its life?Check it with the cost per wear calculator if you are not sure.