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We actually kind of like the featured fashionista, Kate Chapman, in this week's edition of New York magazine's Look Book, if only because she straight-up admits that she sometimes looks "like a crackhead." Oh, if only all the other Look Bookers were so self-aware, the world would be a better place. Anyhow: Miss Kate works at Jen Bekman's gallery and can be seen walking around, sockless and in linen pants, in the middle of winter. She describes this look as "pretty classic and downtown-preppy," inspired by Debbie Harry, and explains her bleached hair as a rebellious move inspired by life at Wake Forest. She also notes that her headband is taken from her "ski bin," which we believe is where Kate stores dirty pictures of Bode Miller. Good to know, right?

After the jump, Intern Alexis looks to Michael Weiss, Jen Lancaster, and Annie Karni for help understanding Kate's crackheaded style.

Michael Weiss, managing editor, Snarksmith

What did Kate wear to her debutante ball?

Like Kate really remembers. She doesn't take such retrograde haute bourgeois bullshit seriously. She only had one because it's something her mom wouldn't shut up about and one of her college advisors hinted it might not look so bad on the Amherst early decision app. And no, she doesn't find it especially amusing to hear the "Westport township answer" of "braces, taffeta, and a guilty smile."

Besides a turtle fur bandana, what other treats can one find in Kate's "ski bin"?

A half empty box of Tazo Earl Grey tea, a yellowing photograph of Javier, her ex-boyfriend from that amazing Habitat semester in Belize, a hot cocoa-thumbprinted copy of Sein und Zeit (Eng. trans.) for those long, lonely rides to the top of the mountain. Also, a pair of earmuffs her grandma made, bleach, the Wake Forest alumni magazine (Winter '05) with a dog-eared Class Notes page. Oh, and two kilos of uncut cocaine.

Says Kate: "Socks are uncool." What else does Kate find uncool?

It used to be SUVs and the capital gains tax, but in recent years, ArtForum editors who don't return phone calls are making a pitched effort at ascendancy, as is the human papillovirus, and war.

What would Debbie Harry have to say to Kate?

"Where do you summer?"

Jen Lancaster, author of Bitter is the New Black and proprietor of Jennsylvania

What did Kate wear to her debutante ball?

Possibly pearls and gloves, definitely flippers, chain mail underpants, and of course rocked some dry/damaged hair-origami do. But not socks. That's for damn sure.

Besides a turtle fur bandana, what other treats can one find in Kate's "ski bin"?

Skis, of course! A shrine to Bode Miller complete with minibar and mixers and self-loathing.

Says Kate: "Socks are uncool." What else does Kate find uncool?

Seat belts, carbon monoxide detectors, speed limits, OSHA, the disclaimers on McDonald's Hot Apple Pies, mattress tags, public school grads, air bags, folks who actually do crack instead of just looking like it, crosswalks, slogans that make sense, Civil War Reconstruction, child-proof caps, virgin hair, safety goggles, and people who love the contemporary art scene AND the art God, they're such posers.

What would Debbie Harry have to say to Kate?

"The tide's never too high for you to wear socks, bitch."

Annie Karni, reporter, Long Island Jewish World

What did Kate wear to her debutante ball?

I get the impression that Kate didn't discover her hideous-edgy/crackhead-preppy combination until her Wake Forest days, when she finally blossomed into the unique butterfly she obviously is today. For her debutante ball, though, Kate just wore her soft, straight brown hair in a simply and ladylike French twist. Her dress was inoffensive and unmemorable, and would never have gotten Kate noticed by the Look Book.

Besides a turtle fur bandana, what other treats can one find in Kate's "ski bin"?

Hidden beneath ski goggles and long underwear, Kate's little book of inspirational mottos is stashed away, next to her stash, in her ski bin. A sampling of Kate's words of wisdom, which are good for all of us to review before going on ski trips:

• No Socks or Knee socks
• This is NOT the dress rehearsal
• What Would Debbie Harry Wear?
• Gross Stuff is Not Art

Says Kate: "Socks are uncool." What else does Kate find uncool?
What else does Kate find uncool?

This is a toughy, because Kate is sending some mixed messages here: socks are "uncool" because they make her ankles look too big; Bode Miller is not cool enough because he's too small; the "scene" is cool, but the art is "gross" — so where does that leave us? I'm totally baffled. Maybe all underwear is lame? I give up.

What would Debbie Harry Say to Kate?

She'd say, "Hey, girl! You look a little like a crackhead, but it TOTALLY works!"