Those chinos look good. The painter shirt looks a little short though, do your sides show without the white shirt underneath?
The fit on this short is bad in my opinion although I love the way it looks. I think peopl need to remember that button up shirts are best when tailored to fit. Lots of people try to buy these to fit off the rack and they end up looking bad
I don't know how much the thighs on mine stretched out, but they got considerably softer and more comfortable. Also, the waist stretched out a bunch letting them sit a little lower, effectively loosening the thighs, I suppose.
I just received my WG indigos, and they are very tight on my thighs, butt, and waist. I'll report back on the stretching, but I've had them on for about 10min now and they've stretched some already.