DJ Chelsea Leyland Shows Off Her After-Hours Style In Williamsburg

In a vast city filled with dancers, DJs, and the dark spots where they meet, Chelsea Leyland is always in the spotlight. Over the last few years, she has become one of the most familiar faces, both behind the decks and in party slideshows. With clients like W Hotels, the BBC, and Vogue calling on her spinning services, she's always at the right event, no matter what country it's in. With all that partying and posing, it's no wonder Chelsea's mastered the perfect, edgy, yet casual night-out style. So, we've tapped her to show us how to dress for three late-night occasions in her favorite NYC 'hood — Williamsburg. Be prepared to take notes — you're about to get schooled in 9 p.m. to 5 a.m. style by a true master.

Photographed by Michael Flores


9 p.m., Drinks Brooklyn Winery:
Yes, folks, true wine culture has at last arrived in the PBR bastion of Wiliamsburg. In a beautiful, wood-accented, modern bar and restaurant, practiced sommeliers offer perfect pairings of beautiful small plates and vintages from both Brooklyn and parts beyond. Oh, and since it's still in BK, you can take home your preferred varietal in a growler from this casual, inviting date spot.

Dress Code:
"This may be a little more conservative than my usual look — just a simple black dress — but it's perfect if I'm going to an event and want to avoid feeling too casual or too dressed up."

Local Love:
"I love Williamsburg because everyone is just a little bit nicer than in Manhattan. People here seem a little more down to earth, more real. Heck, you can go to the shops in your pajamas! Also, the restaurants are amazing. I love that everyone is obsessed with organic this and natural that (as cliché as that may seem). I also love the vintage stores, the flea markets, the antique shops, the record stores, Maison Premiere's $1 oysters before 7 p.m., the list goes on and on."

Cole Haan Chelsea Double Platform Pump, $428, available at Cole Haan.

Photographed by Michael Flores
11:00 p.m., Bowling at Brooklyn Bowl:
If you don't like bowling, we don't want to know you. The lanes here are forgiving, the decor woody, retro and oh-so-Brooklyn, and the fries are fan-freaking-tastic. It's everything you love about your old neighborhood alley with an of-the-now, night-out vibe, and a soundtrack to match.

Dress Code:
"Obviously, this look is casual, but adventurous. If I'm wearing this jacket, those jeans, and these booties, I'm probably asking for an evening filled with a little excitement."

A Night Owl's Life:
"I'm not always living a 9 p.m. to 5 a.m. lifestyle — but it does happen. It's usually due to the fact I have no body clock, travel a lot, and am not really very good at going to bed early. Look, I'm a DJ. If I'm not out working, I'm usually sitting in bed in front of my computer."

Cole Haan Cassidy Bootie, $268, available at Cole Haan.
Photographed by Michael Flores

2 a.m., Beers and a Band at Brooklyn Bowl:
Don't think that just because this place has a few neon-kissed lanes and a rack of retro bowling shoes that it isn't a totally fun drink spot and rock venue. Only feet from where crowds chuck balls is a large dance floor, surprisingly impressive stage, several bars sporting solid acts from all genres, an enjoyable drink selection, and, yes, cute singles.

Dress Code:
"This is a true night-out look — a little darker, a littler sexier. With a blazer, shorts, those shoes, and a shoulder-slung bag, I'm up for anything — drinks, dinner, who knows?"

Absolute, Drop-Dead, Favorite Track Right Now:
"'BTSTU' by Jai Paul. The beat is amazing, it's British, and reminds me of the music I heard growing up in London."

Cole Haan Sabrina Loafer, $218, available at Cole Haan.
Maria Sharapova by Cole Haan Kirby Crossbody Bag, $248, available at Cole Haan.
Photographed by Michael Flores AdvertisementAdvertisement