I know what you’re thinking, and, no, Nicole and I have not unexpectedly sprouted adam’s apples. This is Jason and his best friend, Tim. I styled them for dinner with Marcus and Bethany at Flying Pie last Thursday.

Jason and Tim are basically boos. They have been friends since before their voices changed, and their senses of humor always seem to be perfectly in tune. Like Nicole and me, they are always doing stranger and more extreme things to make each other laugh.

I’m pretty sure Tim thought it was a funny joke to suggest I dress them out of my closet, but I knew I could create genderbending outfits that could still pass as legit street fashion. I started out with menswear staples, vests, trousers, and loafers to ground the looks in the familiar.

Jason wore a blouse that Lisa Sanchez gave me. It has great embroidery detail and a billowy shape. There’s a little bit of pirate, a little bit of hippie, and a lot of plunging neckline.

Tim wore a sheer floral number that fits me like an over-sized kaftan but fits him like a slim men’s tunic. The only thing that throws it off is the print: worthy of grandma’s wallpaper.

Nicole gave this vintage blue velvet vest to Jason for Christmas. I love how rich the velvet looks with my jewel toned silk scarf.

I think these outfits work because they’re built around classic masculine silhouettes. The items from my closet just add richness and whimsy. Most importantly, Jason and Tim wore the looks with total confidence, which is really all it takes to pull off any look, genderfuck or not.

Le sigh. Androgyny is so sexy. I take pictures of such attractive people.

So a pirate walks up to a man in a dress…