Trade clothing with friends.
Hopefully, you have a solid #menswear #clique, and you surround yourself with well-dressed friends. If you're lucky enough to fall into this category, see if you can arrange a mutual trade. Sneakerheads already do this at events like Sneakercon, and it's a practice that can easily be applied to clothes. Take a walk through your friend's closet and select pieces you're itching to wear, and hopefully he'll pick up some pieces he'll want to wear in yours. Everybody wins.