I have tried buying shoes in the $20-30 range in the past, but they didn't last long. I then decided to bought from brands like Clarke and Ecco and my current Clark shoes (resoled with natural latex) and red Ecco sandals are still in good condition. I even got a pair of men's brogue shoes from Skechers when I had to travel to cold Tokyo last Jan. I wore then recently to office and a male colleague commented about them looking heavy and he seemed shocked when I told him they are men's shoes. Hee.
Since last year, I have been more adventurous in buying shoes online from Beyond Skin (peach colour shoes and black sandals with old Camper sandal straps recently sewn on), Luludu crotchet shoes (which are very comfy and provide barefoot walking experience), SoleRebels shoes (almost black shoes with V-design tips, ethically made in Ethiopia with soles from car tyres) and The Root Connective shoes (in cranberry red, ethically made in Guatemala). The customer service staff or founders of these shoes companies were friendly and helpful when I emailed them to return and exchange for the right sizes of a few pairs of the shoes. Even though it was a hassle to go to the post office, luckily the experiences were pleasant. Happy with my current collection of shoes :)