12/28/2011 04:25 pm ET Updated Oct 11, 2012

How 'Seinfeld''s Elaine Benes Became My Unlikely Style Icon (PHOTOS)

For some time now, I've been wanting to try a look that has become de rigueur on street style subjects and quirky it-girls like Alexa Chung: long vintage dresses paired with no-nonsense brogues. But I've always hesitated for fear of looking frumpy. Oftentimes, the ladies I admire for pulling off these too-cool-to-care ensembles with aplomb are ethereal model-types who could don a potato sack and still look delicate. And thus, I stay in my comfort zone of skinny jeans, ballet flats and preppy-chic staples.

But after spending last week watching "Seinfeld" reruns, I drew sartorial inspiration from an unlikely source: Elaine Benes.

In her funky retro frocks and practical oxfords, Elaine made wardrobe choices that mirrored her feisty, nonconformist personality. Unlike many of the downtown beauties who embrace decidedly un-sexy vintage garb in an attempt to look effortlessly cool, Elaine truly owned her look. And though she favored a more tailored, corporate-friendly aesthetic (hello, shoulder pads) in later seasons while working for the J. Peterman catalogue, I recall long shapeless dresses and unisex footwear as the hallmarks of her style.

*Scroll down to see photos of my "Elaine-ian" outfits*

Perhaps Elaine's style confidence resonates with me more than today's trendsetters because I watched "Seinfeld" religiously throughout my formative years. And though I'd never admit to wanting to cop her look as a trend-following eighth grader, a search through my childhood closet while home for the holidays surprisingly yielded some Elaine-worthy finds --namely, a couple of shoulder-padded, floral dresses I owned in the early '90s. Back then, I paired them with cropped jean jackets and delicate sandals, but today I'd give them a more utilitarian spin.

Elaine's sartorial instincts were not always spot-on (remember when she put the "urban sombrero" on the cover of the Peterman catalogue?), and some of her styling choices need not be repeated. For example, I will not be wearing white ankle socks with my oxfords anytime soon. Instead, I plan to stick with my go-to black tights. But with her fearless fashion sense in mind, I visited two popular New York vintage troves in an effort to break out of my rut and seek a loosely interpreted version of her look. First up was Nolita boutique Frock, where I tried on a navy Yves Saint Laurent number with a boxy coat. There was something about its voluminous silhouette that I found Elaine-ian (though I'm not sure whether she ever wore polka-dots). Next, I modeled several printed retro-style numbers at West Village shop Zachary's Smile. I fought my urge to dress them up with pumps, high-heeled boots or girly flats and a ladylike coat and instead added edge a la Elaine with sensible brogues and an oversized blazer.

The verdict? While I won't be completely revamping my wardrobe (or wearing white ankle socks -- ever), I resolve to incorporate Elaine's tough-meets-feminine sensibility into my own styling choices, and be a little more undaunted when it comes to taking risks. I won't, however, be copying her dance moves.



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