I will be working at IndySwank on Super Bowl Sunday from 12 to 5. IndySwank will also have a special Super Bowl site at City Market. Stop by and visit either location this weekend!

Glance through photos of Coco Chanel’s earliest day wear and you’ll see a whole galaxy of frumpiness: long, shapeless jackets layered over even more shapeless calf-length skirts. I place them in three basic categories: slightly frumpy, very frumpy, and incredibly frumpy. You won’t find a hint of the timeless elegance that followed Chanel’s comeback in the 1950s. How could the same woman be responsible for both looks? Times changed. And so did Chanel.

What about you? Are you still clinging to a fashion philosophy handed down by your mother, your peers, or some fashion magazine? You’re in good company, especially if your Mom is still one of your style editors. Unless you count the times she tried to dress me in my brother’s hand-me-downs, my Mom and I never fought over clothes when I was growing up. If she thought an outfit was tacky, I changed my clothes and added another rule to my book––the same book that hogties my imagination when I’m getting dressed today.

My brain has relentless style referee who calls all the shots. Can I wear this purse with those shoes? Is this too much or too little jewelry? Can I pair these two colors? Does this pattern go with that one? Is this too sloppy? Most of the time, I err on the side of conformity. What a pity. What is the point of living in an age of artistic freedom if you aren’t going to use it for greater expression? Why are we afraid to innovate and invent with fashion? I guess we all want to be unique, but not too unique.

That brings me to this outfit, assembled by Annie Stoltz, a local stylist who composed it from vintage pieces found at Indy Swank. I wouldn’t have put these garments together on a bet, but they work in such a compelling way. Why? Because they have just enough in common to be harmonious. I take it as inspiration for being more playful with clothes. What about you?

What would happen if you loosened up and had more fun with your clothes? Or maybe you’re already a pro at styling yourself. Either way, I like the idea of being liberated from an inner style critic. That’s why I’m sponsoring the Freedom Style Fest, a photo contest featuring the imaginative styling of Dressed Her Days Vintage readers.

From now through the end of February, I’m inviting you to snap a photo of yourself wearing something that’s cleverly styled, but definitely outside the box of conformity. Vintage or thrifted outfits only, please. Whether it’s way outside the box, or just enough to take you a little beyond your comfort zone is up to you.

To judge the contest, I’ve recruited two style experts, Sujei Lugo, America’s Most Glamourous Librarian, and Ingrid Henny, the Style Savvy Librarian, so dubbed after a jury of their peers named them last summer.

You can participate two ways:

1)   Post your photo on Twitter using the hashtag #FreedomStyleFest. It would also be helpful if you added @DHDVintage to your post.

2)   If you don’t have a Twitter account, send your photo by  Email.

The winning entry will receive a copy of The Gospel According to Coco: Life Lessons from the World’s Most Elegant Woman plus a $50 gift card.

Let the style show begin. I can’t wait to see what you’re wearing!

Life is short. Wear the good stuff.