I just dropped off three pairs of shoes at the cobbler.

New heels for my Eject boots.
New heels + heel taps for my Franco Sarto Pacayas
Rubber soles + heel taps for my Fluevog Lancianos

The price is fair for the work the cobbler is doing, but I could buy a new pair of shoes off 6pm for the same price.

I used to buy one pair of winter shoes and one pair of summer shoes each year, wear them down to the ground and then toss/replace the next year. Now that I'm going in for the shoe wardrobe, it seems like the soles of "nicer shoes" are still going to wear through at about the same pace, with the only difference being that the uppers are still in good condition. It is worth it, right?

How often do you resole your shoes? Or rather, when do you decide it's time for a pair to give up the ghost?