It all depends on use. I'll buy top of the line because it has a generally well-deserved reputation for lasting forever, and I'll keep it forever. Snap-on tools over decent but not in the same league stuff by Craftsman, SK, etc. I could buy a pair of Yukon Charlie's snowshoes and go 80% of the places my more-expensive MSR, GV, or Louis Garneau 'shoes will take me, but I've found out through use that mine will take the abuse of icy, rocky hills & mountains and not fail when I can least afford it. I've talked with plenty of people who spent almost $300 on a pair of MSR Lightning Ascents just to do laps around the golf course, too. They're usually wearing Arcteryx, Helly Hansen, or whatever the latest fad brand is. It's like the yoga pants of outdoor gear.
Sometimes the most expensive stuff has little features missing from otherwise serviceable lower cost stuff. My EMS rain jackets have pockets low on the jacket and they're covered up by my pack waist belt. Unbuckling with heavy gloves on is a PITA, but if you spend the money for Arcteryx or Outdoor Research you get pockets higher on the jacket and out of the way of pack belts or climbing harnesses. (My solution was to replace the waist belt with a longer one that I can loosen at the buckle, $3-400 for higher pockets was a little too much for me.)
Sometimes the top of the line stuff is made in more sizes; some Asolo, Salewa, and Keen boots come in wide sizes that fit me better than other brands that may or may not cost less. Merrell, Vasque, and Oboz all fit me terribly.
I rarely pay full price for my outdoor gear, there are plenty of discount & closeout sites, some offer cash back, and if you wait a week or 3 you can often find branded stuff on sale for close to store-brand prices. A few years back I got 3 pairs of closeout TNF ski pants from REI Outlet for about $125, or about 25% of MSRP. One pair I gave to a friend because my waist size was between 2 different sizes. Buying rental gear when it's being replaced is a good way to get stuff for around 50% off, if you know how to inspect it or are willing to take a chance. I bought a pair of rental MSR Flight 2 poles for $60, or about 1/2 price, sight unseen and the only wear on them was from storage & handling.