Lynette Nylander grew up with a mother who ironed her underwear. “She took immense pride in the way she put herself together,” says the London-born, New York–based fashion critic. “She thought it was important that I understood that as well.” For Nylander, who served as the creative and editorial director-at-large of CR Fashion Book and is currently the U.S. editorial director at Dazed, good style lies in its contradictions—a little high, a little low. Something delicate but “a little fucked-up.” The art is in the clash.

And planning an outfit begins with a single piece. “I ask myself, New thing? Old thing? Tailored thing?” Armed with the answer, Nylander ventures into her closet, a former “apartment-engulfing fungus,” which she has since wrestled into a state of organized chaos. “The results can vary, but the beauty is that it all comes back to different parts of myself that I’m really comfortable with. It takes years to get to that place.”

For Nylander, that comfort is the key. “I’m messy. I get candies stuck to my bag linings. I need my clothes to work hard and make me feel free,” she says. “In the end, it’s the swag that sets a look off, never the brand name. Anyone can have that."

Lynette Nylander's Rules to Live By:

1. Always understand that what is for you won’t go by you. This has served me well professionally, personally, and romantically. It helps soothe the wound of not getting a gig you wanted, or when the vintage piece you went back for the next day was gone.

2. Always date the future and marry the present. Live in the freaking moment. Marry the hell out of today, and have a flirty relationship with what comes next. Treat the future like a casual fling, and don’t be dictated by it. What you know is that today is right here, right now.

3. Always believe in the power of poor taste! I don’t want anything too glitzy with no chaser. I consider myself a lover of the dichotomy of high and low. Vintage Saint Laurent dress to visit the dosa guy in Washington Square Park—perfect! Monkey Bar, then Drag Race reruns after—ideal! My new one: I dream of de Gournay wallpaper to frame the thrifted photo I got for no money.

4. Never skip cocktail hour. Do this as formally as you can. Bar coaster, the appropriate glass for your drink, and lots of chatter about the day’s comings and goings. This, I am sure, will add years to your life.

5. Never be afraid to do things alone. There’s nothing sadder than not being able to be in your own company. Meals, vacations, theater shows, cinema trips. Know yourself, goddamnit.

6. Never sleep on bad sheets. Criminal!