What is the longest that a pair of shoes has held up for you? For me, it is an astounding 18 years. That’s right. 18 YEARS. That is insane to me. I was so anxious about spending $80 when I went to buy those Chacos, but in the long run the fee was well worth the value. At the same time, Kris opted for a pair of shoes that cost less, and has since had to buy five pairs in the time that my one high value pair has lasted. It is so important to learn when to pay the higher fee for the higher value.