How to Look Ugly-Pretty and Still be Chic

not so repulsive anymore.

not so repulsive anymore.

Famed fashion blogger Leandra Medine made a fortune from her street-style looks and humorous writing on the idea of “man-repelling,” or clothes that are worn not for the sake of picking up men but for the sake of fashion or expressing your own identity, however absurd it might look.

The description of something as “ugly-pretty” has been around a long time, a phrase borrowed from the French jolie-laide. At first, it seems a contradiction. But fashion is all about interpreting style in your own unique way, and sometimes that means turning traditional pretty-girl looks on their head. And in this post-modern era, creating your own identity can mean reversing or completely eschewing traditional gender roles of femininity and masculinity. Can something ugly, like a pair of Crocs (come on, would you wear them on a grocery run to Trader Joe’s?), be made pretty, when worn with the right outfit and attitude? Take for instance, the return of the Birkenstock. Never thought that would happen, right?

Fashion designers concoct strange shoes and downright hideous dresses all the time in the name of creative experimentation. But this fall season it seems certain jolie-laide trends are in: mismatchy prints, shower shoes and cartoony animal-ear hats among them, not to mention that other trend that keeps sneaking back, the one where you wear frilly socks with high-heels.

We like to think there are no rules in fashion, but there are definite guidelines. Here, we poked fun at them with our top 10 rules for looking ugly-pretty:

1. Don’t look too pretty. No girly ruffles, peplums, silk chiffon dresses. And, ugh — no pink.

2. Wear just enough makeup to look like you’re not trying.

3. Spanx are off limits. Let it hang girl.

4. The crazier the print, the better. Tartan and polka dots? Yes.

5. Wear gentleman-inspired pieces, like a dashing blazer, spectacles and chunky gold watches.

6. Sweat pajamas are not too informal.

7. Rock a bold, bold lip. Like deep eggplant purple lipstick.

8. Curl your hair, then sleep on it and don’t wash it for a few days. Spritz dry hairspray all over, then fluff it up with your fingers for a I-slept-in hairdo.

9. Pair something super sexy, like a dress with high slits, with something kinda ugly, like a cargo safari jacket or a sweatshirt with a cartoon Mickey Mouse.

10. Don’t match. Dress like 90s grunge never went away.


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