Shorts are the one thing you don't wanna skimp on if you're gonna be in the saddle all day. But for rides less than two hours or so, I have found regular street shorts with regular boxer briefs work fine, provided the boxer briefs are not too loose.
As for socks, I found a great way to save money on those. I just get the Walmart ankle socks ... BUT ... I get the big ones in size 15. That way they come up 4-6 inches or so above my ankles. The regular sized ones always shrink up too small, but the size 15's are perfect. Very cheap too, and come in both black and white.