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Bandage Dresses

A really cool French girl I interned with years ago perma-borrowed one of her mom's Herve Leger dresses from the '80s. Before the label relaunched in 2007, she wore it all the time. No one knew what it was. It was cool.

Of course, now those bandage dresses are everywhere. To turn it into something more than a predictable prom dress option, I'd toss on a tie-front blouse or sweatshirt—transforming it into a pencil skirt—and wear it during the day. With open toe booties, it'd be, well, cool.

Wellies

If you've ever walked across a college campus in the rain, you know that wellies are a higher education necessity. That's probably why my mind ties them to lazy collegiate outfits. I feel kind of weird wearing them now, like I should be more adult or something.

Making them intentionally part of a look, though, could turn that around. To do that, I'd trade out blue jeans and a knapsack for something either ridiculously fun, like a bright, sparkly dress, or New England summer camp-y, like tattered khaki shorts.

Colored Denim

You couldn't open an Us Weekly last fall without seeing at least five actresses in highlighter bright denim. I, too, bought some Crayola-worthy pairs and wore them in place of my regular blue jeans.

Now instead of treating bright denim like standard blue (wearing colored pairs with my white button down blouses and striped t-shirts), I'm freshening it up by going for head-to-toe color. Bold denim might not be shocking anymore, but I think this is—in a good way.

Ballet Flats

The great Ballet Flat Surge of the early 2000s means I now feel more "current" sliding into menswear-inspired loafers or brogues.

But with looks that are designed to show off slim ankles (loose, cropped boyfriend jeans, printed, matchstick-skinny pants) a quiet, barely-there ballet flat just makes sense.

Tribal Prints

Last year Topshop and H&M's most popular pieces looked like cut up tribal blankets, the kind that people drape next to fireplaces in log cabins and ranches. On clothes, it looked snappy and new. I bought a bunch of it to wear as part of off-duty, relaxed looks, and so did everyone else.

Now I feel like I need to wear the print in a less festival-friendly way to reinvigorate it. I bet ditching faded denim and feathered accessories for tailored, high-waisted pants and a blazer would do the trick.