Take, for example, the following pics from Vogue Homme Japan.
This is Lady Gaga's alter ego: male model Jo Calderone. I know performing drag kings that don't quite pull off the transformation like she does, but they'll agree that it's an art. I think she looks downright sexy in drag and the spread makes a lot of (fashion) sense when you consider the trends.
Also this month, PAPER Magazine features Michelle Trachtenberg plus 11 more ladies getting "In Touch With Their Masculine Side". She sure has come a long way since Harriet the Spy. Apparently, Trachtenberg had no problem impersonating a dude for a day. "My sense of humor is very dirty," she told the magazine, stroking her facial hair. "Most of my friends are guys, except a handful of girls. I talk and think like a boy."
Other notable ladies include model Jenny Shimizu (who has gotten "in touch" with her masculine side for countless magazines) and designer Charlotte Ronson (who seems to channel her DJ twin sister in this pic). You can read the article and view the rest of the pics here.
If you're looking to "drag it up" for the Fall season, don't forget that button up shirt is a timeless classic. Pair it with the basic slacks and suspenders or add a faux-leather vest for the harder look like Jo.
To get right hair to compliment this look, take out the hairspray and a hair tie. Make sure to poof the top like Tracy from the Real L Word on the cover of BOUND magazine.
It'll go really well with a crisp white shirt and trousers, but don't be surprised if cute baby-lesbians hit on you. Wink and take it as a compliment.