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

The Economista Finds Her Wings

by Sara Minard – September 30, 2009

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….

About the Author: Sara Minard

Sara lives by two maxims in life: "Foie Gras Taste on a Spam income" and "Work to Live." After graduating from UW-Madison, she spent five years as a production assistant at a luxury chocolatier - Lucille Ball, anyone? Her life took a turn for the strange after being dumped by her boyfriend's mother (that's worse than a break-up via Facebook, right?). She decided Madison wasn't big enough for the three of them, so she packed her truffles and moved to Chicago. Her work life in Chicago has been a mix of working in and managing high-end restaurants, sidelining as a "picker" for a vintage couture boutique with locations in D.C. and Las Vegas and, when the season is right, working as a forager for some of the fanciest restaurants in the city. Currently, she splits her week between a condo in the Gold Coast and an Indiana log cabin next to the lake that she shares with her steady, a Border Terrier and their cat, Mr. Man. If you can't find her in the kitchen – cooking as a private chef for her Chicago clients, canning or pickling something – check the local thrift store. You might just find her adding to her muumuu collection, or finding super sexy seventies and eighties designer dresses for six bucks. Sara definitely has something to say about the art of looking and living fabulously on a shoestring budget!

Posted in Fashion Forward