08/20/2012 08:16 am ET Updated Oct 20, 2012

I'm A Lady, But I Dress Like A Boy (PHOTOS)

Years ago, I was having dinner with a couple of girlfriends who were visiting from San Franciso. I'd taken them to a restaurant I'd been going to for years, a nice sit-down joint in the West Village well-known for dishes such as beef marrow with toast points and onion marmalade. And while not much else has ever mattered to me around meal times besides the delicious things I'm savoring in my mouth (i.e. Dinner conversation? Shut up and pass me that plate of crispy bacon fat!), this night was different. This night, in fact, was a revelation. My companions happened to be the sexiest women I'd ever known: a duo of stone foxes possessing the perfect amount of natural beauty, cleavage, and most importantly, swagger. And here I was, finally, with orchestra seating -- enough proximity to catch the light reflecting off their perfectly glossed, full lips, and ask them how they did it.

Both women were bartenders, and understood things about drunk men, eyeliner and Victoria's Secret bras that would take me another half decade to even begin to glean. Their way of dress was meticulously deliberate, a fine-tuned balance of masculine and feminine: variations of a fitted blazer layered over a slinky top and a pair of snug trousers. Perhaps a skinny scarf wrapped loosely around the neck. One of them explained to me, "It's like body armor. Without the makeup and the clothing, I feel vulnerable." (Meanwhile, the simple blue cotton sundress that I had donned in an effort to look cute in an understated girly way was now screaming "homely-dork-who-enjoys-milking-cows-for-a-living.")

Some women find sexual self-empowerment through barely-there tops, rubber bands masking as skirts, and double-height platform stilettos. And sure, you might evince a certain amount of authority in a flesh-revealing get-up that makes you look like an amateur hooker, where the uncrossing and crossing of legs becomes an uncomfortably delicate procedure. But here, I was being reminded that sexual puissance (large vocabs are sexy, too!) can be derived just as well, and probably to greater effect, when you're rocking a look that's a cross between Marlene Dietrich's menswear-inspired look, Jennifer Beals' steel-welding dancer role in Flashdance, and CK One-era model Jenny Shimizu.

It's a look I've been trying to master since high school: the femme butch. I've always had a penchant for masculine dressing. I despise frills, patterns and "latest trends," and love classic, streamlined clothing. In particular, I love how men can wear the same pair of pants everyday for months and get away with it as long they shower on a regular basis and change their shirts every so often. In high school, I'd wear my dad's shirts, pants and blazers, and red lipstick -- I looked like a clown. In college, I resorted to thrift stores and my boyfriend's wardrobe for all my menswear: pants, cardigan sweaters, dress shirts, pea coats. On winter breaks, my mom would repeatedly accuse me of looking like a homeless person. Now, I think I'm starting to get it. My shopping list includes: Untuckit dress shirts in size small, wool-knit cardigans from the men's section at J.Crew, Bass penny loafers, a Very Sexy Victoria's Secret bra and some smoky eyeliner.

The moral of the story: At the end of dinner that night, the waiter spontaneously comped us no less than three dishes (something I had NEVER experienced in the years I had been dining at the restaurant) -- to which my lady friends thanked him with enough subtlety to make me realize that this happened all the time to them. And now it happens to me, too -- though I'm sure it doesn't hurt that I often write about food and restaurants for a living.

I'm A Lady, But I Dress Like A Boy