How to Dress Like a Boy (in a Good Way)

I was in the midst of a deep, lowdown and particularly painful fashion crush. I suppose I could lump direct blame on all the fashion rags I subscribe to, which, in its very action, is like a drug addict subscribing to High Times. Instead of gazing upon fat nugs, however, I took my time in lingering over high-resolution images depicting teenagers in outfits that exceed the gross annual earnings of more than 75% of the world’s population. Of particular interest to me were the pieces that combined masculine and feminine elements with high/low panache.

Cross-dressing is nothing new. Chanel started building a fortune on the idea from the moment she borrowed her lover’s sweater. Rather than giving it back, however, with a cheeky smile and demure “thanks”, she restyled it so it was tailored to her body, and launched a trend that spread like wildfire in her day. Greta Garbo turned heads in a man’s tuxedo while Katherine Hepburn epitomized female independence in her tailored pants. Even Samantha Ronson (bless her heart), rocks it.

Fall seems like an appropriate time to appropriate the look. After all, why be the chick turning blue in an inappropriate get-up when the temperature plunges? Because open-toed shoes are the first to be crossed off my list once fall hits, I am obsessed with finding an immediate cold-weather counterpart to my fair-weather friends.

Enter Cole Haan. More specifically, enter Cole, Rood, Haan & Co. The new offshoot of Cole Haan offers bespoke footwear for the modern lady, or at least for a modern that purports to be a lady. Look!: http://www.colehaan.com/coleroodhaan/women.html

Kinda sexy in a “devil meets peter” sort of way, right? But like I said, this story is about a crush, not a marriage… no $350 kicks for me.

As a PhD student with no real income to speak of, I have to get a bit more crafty, and a whole lot more thrifty in order to consummate this newfound love of mine. So I started trolling my favorite thrifts for a pair that spoke to me. Before long, I stumbled across the perfect pair – men’s handmade wingtips from the 1940’s. While it is difficult to find current men’s sizes that fit my feet, I’ve found that the further I go back in the sartorial timeline, the smaller the shoes get (why?… nutrition, immigrants, cross-gendered foot-binding???). So I bought the wings, spent $16 and effectively saved myself $344 in student loan money. I’m a genius! Now I wonder how much that tuxedo will run me….