Well, a good way to get into the groove with this is to stop shopping for clothes in the men's department completely. It can take some effort, but you can find plenty of clothing in women's departments that pass as mens clothes as well. Arguably, this is easiest with jeans, so buy some women's jeans that are not too girly. It's trickier with tops, but plan your outfit in advance.
With clothes shopping, it's best not to buy individual pieces blindly. You want to work out a complete outfit and find the pieces that make it up. My favorite thing to do is to take cues from pictures of stylish celebs in their own clothes. They have expert stylists help them plan their outfits, so we can benefit from their efforts.
My fav andro looks right now are skinny jeans with boots or sandles, t-shirts or turtlenecks and that sort of thing. It's really not very hard.
~ Lyric ~