Winona Dimeo-Ediger

5. You start feeling insecure about the distinct lack of rappers in your social circle.

Justin: I know you know that I made those mistakes maybe once or twice. Me: Once or twice? Really, Justin? Justin: And by once or twice I mean maybe a couple a hundred times. Me: Right. Now we’re on the same page.

I ask myself these questions every time I’m considering a purchase, and if the answer to any of them is “no,” I put it back on the rack.

Our fierce fashion ace Winona Rose helps our editor Katie Tandy avoid the purgatory of endless Old Navy trousers.

These things could never happen. But WHAT IF THEY DID?

The other day I met up with my friend Paige at a coffee shop. She went to the bathroom, came back, and said, “So, the toilet paper roll was empty, and I almost didn’t put a new roll on, but then I thought, ‘Be the change you want to see in the world,’ and I changed it.” She beamed triumphantly, and I said, “Paige, you’re a hero.”

Dressing your age is much more complicated and personal than it might seem. Only you can decide if that “awkward” feeling about your revealing outfit came from a place within yourself or from outer pressure to look or dress a certain way.

Dear Winona,

fashion entrepreneur. advocate for human trafficking victims.

Maybe you want to downplay an area you’re feeling insecure about, maybe you’re not in the mood to wear eye-catching colors, but that doesn’t mean you have to buy clothes that effectively make you disappear completely.