Started out my professional life doing the $10 shirt thing from kohls, jc penny, etc. (have about 5 of these), but I have been phasing them out lately and going for a little costlier ~$30 type shirt from men's wearhouse, express, Jos A Bank. There is a huge quality and look difference between those tiers and some of my $10 shirts are wearing around the collar , sleeves, and elbows (after about 4 years of use). At this point, I don't see any reason to go higher quality than that $30 tier, they work well with/without tie and with/without a suit, and they look really good. These shirts can be machine washed/dried and don't require ironing if you take them out and hang them up.
I also don't wash them very often, I have enough shirts to last me 3 weeks or so, 4 days/week and I wear multiple times before a wash.