I do it on a case by case basis. Sometimes I go quality but on others cheap. I'm more interested in functionality that looks. I can't see spending lots of money on something that will last a infinite number of uses if I am only going to use it a few times in my life time. If I will be using it ten times a day for a lifetime I will spend the big bucks to get quality but if I only anticipate using it a dozen times total I am less inclined to spend much on it. I rarely sell anything so I pay no attention to resale value.
I spent $150 for my last pair of work shoes that lasted 5 years. For goofing around home in the I spend $2 or $3 for a pair of flip flops two or three times a summer.
Some tools are beaters, some are quality. I go by what I intend on doing with them. I have cheap screwdrivers that are combination pry bar, scraper, chisel, and occasionally screwdriver. I have quality screwdrivers for stubborn screws and where not messing up the screw is important.
So in the end I can say I buy once, pay once. It's just that 'once' may only need a low or medium quality to fulfill the 'buy once' criteria.
One other point. High price doesn't always equal quality and inexpensive doesn't always mean junk.

