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Dear Matt:

After seeing Hedwig and the Angry Inch, I’m inspired to go full drag this Halloween. The problem is, I have no idea how to start! As a straight male who’s never dressed up in drag before, I have zero fashion sense, zero knowledge about makeup and wigs, don’t know what size dress I wear, or what outfits to avoid because they make my butt look big. And where does a fellow go to find platform heels for guy-sized feet? The nice ladies at the makeup counter at Nordstrom tried to be helpful, but this goes beyond their training. I hope there’s a place in San Diego where a guy can go to get a makeover, and I hope that you’re just the man to ask.

— Michael…or Michelle? Vista

The elves motored to Hillcrest for this one. Hillcrest at Halloween: what better playground for the aspiring gender illusionist? Well, Hillcrest in the middle of May, too, I guess. Anyway, the clothes, shoes, makeup, et cet. — that’s the easy stuff. Plenty of outrageous vintage stores on Fifth Avenue. Tata Lane, on Evans Place, sets aside guy-sized outfits, shoes included, for rental at Halloween. And they’ll have a makeup artist available that weekend. So will Lips, the wiggy drag-and-dine at Fifth and Nutmeg. A gracious and accommodating Tootie (www.tootie.com), who does a dynamite Cher, condensed her nine years of experience for you. So pay attention.

Sez Tootie: A drag queen’s best friends? “Big hair and duct tape, honey.” Big hair slims the appearance of a man’s larger face, neck, and shoulders. And it’s sexy. Ditto big eyelashes. Warns Tootie, “Leave the skin-tight dresses to the pros.” Got a beer gut? A skirt and loose top is your best fashion choice. A plunging neckline enhances the illusion of a slim face and neck and offers a chance for some naughty cleavage, achieved with the aforementioned duct tape. Yank your “back fat” (Tootie’s words) around to the front and tape it in place. “The higher the heels, the closer to God,” sez Tootie. Sexy spikes lengthen the appearance of your legs.

Of course, you can wear all the glamour rags you want, but if you don’t stand and move like a woman, then you’re just a nose tackle in a ball gown. Hold your chin in a bit closer to your neck and chest than usual. This also facilitates looking up sexily through your explosive eyelashes. Keep your elbows in, close to your body, to give you graceful arm and hand gestures. And most important, walk by placing one foot in front of the other, not with a man’s typically wider gait. Think “matador,” not “stevedore.” That also makes your butt look cute walking away, sez Tootie coyly. As we tumbled out of the red velvet cave that is Lips, Tootie called after us, “Oh, yes, how could I forget! Shave everything! Immediately!”

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