The Insider: Ray Siegel

Devouring Ray Siegel’s in-the-know posts on is like reading a syllabus of what’s destined to be cool down the road—trust us. Shocker of all shockers: the fashion-slash-music-slash-beauty expert is as cool (and crazy-charming) in real life as she is on the internets. Behold. —carlye wisel

Q: Were you really into music pre-Nylon, or did your job there encourage that?
A: Music what I was first interested in, I would say. When I was young, I remember spending all of my time watching MTV, listening to the radio, and trying to convince my parents to buy me new CDs. I’m actually surprised that I didn’t become a music journalist, because the fashion thing kinda came later. But at Nylon, luckily, I get to do both. And then there’s beauty in the mix, too, which I also love doing. It’s sort of just the perfect mix.

Q: Do you have any beauty tips you swear by?
A: I’m really into highlighters. Trish McEvoy actually taught me this tip where you take your highlighter and draw a triangle under your eye—she calls it the Triangle of Light—and it’s a way to cover any sort of darkness. You just paint it on and rub it in.

Q: What would be your perfect New York day?
A: Well, in the winter, my perfect day is not leaving the house, because I hate the cold. But if it’s really nice outside, one of the things I always look forward to is going to Coney Island. I like going on all the rides, and my favorite pizza place in New York, Totonno’s, is right nearby.

Q: What’s the most embarrassing thing on your bookshelf?
A: I do still have a lot of the books I read as a kid, some of which are probably very embarrassing. Actually, my mom just sent me this card from a book review contest that I entered when I was 10 years old. It’s an illustration and a review of Lois Lowry’s Number The Stars.

Q: The Holocaust book?
A: Yeah! I basically had an obsession when I was a child. After I read The Diary of Anne Frank, I almost didn’t sleep for three years because I had terrible nightmares.

Q: What’s your shopping strategy like?
A: I’m the kind of person who likes trying on every single knit sweater. I will go around the perimeter of Barneys and look at every single thing, even if its a designer I’ve never worn before. You never know what you can find, and it works pretty well if you don’t discriminate. I focus more on the shapes of things, and if I think it’s a shape that would look good on me, I’ll try it, no matter what.

Q: That’s gotta be pretty time consuming, right?
A: It’s pretty slow, yeah. I go to What Goes Around Comes Around a lot. They have stacks of a hundred white T-shirts, and I’ll lay them out and go through every single one. The lady that works there is like, “What are you doing!” and I’m like “Nope, this is just what I do!” I make piles and try on all the ones that I think will fit. I spend a lot on T-shirts and sweatshirts and things that I know I’m going to wear all the time.

Q: What’s the worst thing you’ve ever worn?
A: When I was in college and high school, it was just kind of a bad time for fashion in general. Body glitter was cool, halter tops were cool, off-the-shoulder things and tight pants…and I definitely fell victim to some of that. I also wore a lot of stuff that I’m not embarrassed about at all and still wear. I have a Marc by Marc Jacobs denim jacket with crazy patches and studs all over it that I’ve had since high school, and I still rock that.

Photograph by Melanie Galea of The Street Muse.

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A Case for…Cool-Weather Vests

The next month is prime vest season—and I’m not talking about sort favored by Mr. Timberlake or guys who know the sound a Sidecar ought to make in a cocktail shaker. This is a tribute to the ones that keep you warm but not so toasty that you have to disrobe on the subway, and these are the six worth pulling on, stat. —erica

1) Whillas & Gunn Hawthorn vest: That shawl collar alone sells it.
2) Steven Alan fall hiking vest: Reminiscent of an era when mustaches weren’t ironic.
3) What Goes Around Comes Around Mallorca vest: The checked wool has a woodsy vibe, but the leather detailing is much more Milan.

FACT: The dogs working with the U.S. military in Afghanistan are equipped with canine bulletproof vests.

4) Wings + Horns down vest: This is, in essence, the perfect puffy vest—in part because it’s really not all that puffy.
5) Rag & Bone Ashmore hunting vest: Camo that would look appropriate for a 9 PM dinner reservation, especially if paired with slim-cut wool pants.
6) Odyn Vovk sleeveless denim zip-up with leather hood: Don’t let the photo fool you: This should be worn with a long-sleeve shirt, preferably a no-nonsense henley.

FACT: After a run in with hypothermia, Eddie Bauer invested $25 in down and, in 1936, created the Skyliner jacket that was worn by Jim Whittaker when he became the first American to climb Mount Everest in 1963.

1) Available at Gargyle, $158; 2) Available at Steven Alan, $298; 3) Available at Ssense, $395; 4) Available at Context, $506; 5) Available at Barneys, $565; 6) Available at Blackbird, $419 (on sale)

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