There are plenty of ways to do this... this is actually my everyday look now. I try to buy masculine women's clothing, it works very well. For example, I buy a lot of women's blazers, they have a very fitted tailored look to them, and a feminine flare... yet a blazer is typically considered to be a more male article of clothing. I also buy women's oxfords, these are great because they have the design of a boy shoe, with a soft feminine flare... they aren't boxy like men's shoes. For pants I do women's skinny jeans, or pants/trousers. A lot of my pants hit high on the ankle, and a capri look to them, and are much more flattering to my body than most men's pants would be. Depending on your size... do Forever 21 and H&M for cheap blazers and pants. Urban Outfitters for pants. Express for blazers. BCBG for amazingly stylish jackets. Cole Haan for Oxfords. Most of these brands are a little pricey, but totally worth it.
Granted, everyone thinks I'm a woman, and people are really shocked when i tell them I'm a guy, or after they tell them they think I am a FtM. This is a normal outfit I would wear, and this is also me in the photo. It's H&M Blazer, Express shirt, Urban Outfitters pants and a random tie we pulled out of wardrobe. Also, imagine this look with heels or oxfords... both would work =) I normally would wear my hair down dressed like this, and no makeup... but it was a photoshoot so the makeup artists and stylist went all out.
