Winona Dimeo-Ediger

"Your quest to stay true to your retro aesthetic is not impossible. Here are a few tips for incorporating your love of vintage into a modern, casual wardrobe."

Here's what I want to ask the guy who used this airplane bathroom right before me:

1. Dude, seriously?

Career-wise, you’re the boss, or, if you’re not the boss yet (emphasis on YET), you’re the boss’s dream, going above and beyond in every way. You tend to define yourself by your job title, and the thought of letting go of that identity gives you hives (this might be something you want to work on, Group A). Your desk is so beautifully organized it could be part of a MOMA exhibit called, “The Artful Workspace: A Retrospective.”

Here are a few tips for managing a major style transition without going bankrupt/insane.

Instagram: Don’t eat it though, just hold it. With a stiff, outstretched arm in front of a whimsical mural on a decaying brick wall.

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

Dear Winona,

Clothes can be altered. Clothes can be sold. Clothes can be swapped with friends. In the meantime, you have to get dressed every day, and you might as well love the clothes you have right now.

5. No one person can meet all your needs. Expecting your partner to meet all your needs is a recipe for disaster. There is no one person on earth who can single handedly meet all your social, intellectual, sexual, physical, and emotional needs.

Our resident aesthetic ace—with an assist from Drake—offers fashion advice to our Canadian writer Anne, who's sick of the cold and her clothes.