StyleHiving: A Spontaneous Outfit Breakdown

Oh the joys of getting dressed before a date — the plotting, the scrutinizing, the constant need for re-assurance from your friends that you look hot and not in any way slutty, the hours in front of a mirror, the Polaroid pics (how can anyone forget Cher’s over-the-top first-date precautions in Clueless?)…

Maybe you don’t go quite as far as these extremes — or maybe you go embarrassingly beyond — the point is, any girl would be lying if she didn’t admit to at least a slight amount of neurosis regarding this process. But lighten up, ladies, because as I recently discovered, sometimes the perfect date-night outfit can emerge accidentally on its own.
Last weekend I met up with a friend who was visiting with her boyfriend, and a bunch of his guy friends. It was a mellow night — a few bars followed by drinks at one of the guys’ apartment. As I looked around, I realized that my gal-pal and I were completely outnumbered by men. Then it hit me — what a great way to get material for my next column! When I threw the question out on the table – “What should a girl wear on a first date to make the best impression?” — the boys chimed in with the obvious dating rules.

1. “Don’t dress too sexy, or we’ll just see you as an easy lay.”
2. “It’s okay to dress up, but don’t look too dressed up.”
3. “Covering yourself up is good, but not too covered up.”

And so the story goes. Um, okay, guys, that’s nice, but let’s be specific. All of the sudden, all eyes were on me. One of the dudes said, “You know, what you’re wearing is actually the perfect first date outfit… like couldn’t be more perfect.” The others agreed.

Hmm, how did that happen? I woke up late from an afternoon nap and had only a half hour to shower, get ready, and find an outfit suitable for dinner with my parents, followed by a night out with friends. I had to act fast to coordinate an ensemble that would stifle the proverbial family critiques — you know, the “Where do you think you’re going dressed like that missy?”-song that can put a dark cloud over any night — but one that wouldn’t make me feel like a librarian when I went out to the bars.

The end result: a black knitted short sleeve v-neck top from H&M (I bought the top a size larger than I usually wear because I liked that that bigger one was longer, slouchier, and that the v-neck dropped a little lower), black skinny jeans by J Brand, and my trusted black Chanel ballet flats with a patent leather cap-toe. I accessorized with two necklaces — one short, one long, and a mixture of gold and wooden bangles. I looped a black knitted skinny scarf around my neck and threw on a long, Juicy Couture wool and cashmere knitted cardigan in beige.

So what was so awesome about this outfit? Well according to the boys, the low-cut top was revealing enough to be sexy and enticing, and pairing a loose top with form-fitting pants gave the look a sexy, yet “chill” vibe. Most importantly, I didn’t look like a tried too hard – which I obviously didn’t! Let’s here it for getting ready in five minutes!

Here are some options for re-creating the looks.


Twig Deep V-Neck Sweater, $225, Daryl K Rudi Tunic, $203, Neil Sperling Viscose and Wool Split Front Tee, $76


Catherine Malandrino Sequin Elongated Cardigan, $425, Alice & Olivia Navy Chevron Wool Long Cardigan, $169.99, Free People Long Cardigan Sweater, $138


J Brand Skinny Low-Rise Jean in Jett, $158, Juicy Couture Metallic Kate Jeans, $198, BDG Cigarette Leg Jean, $49


Urban Outfitters Heirloom Knot Necklace, $18, Forever 21 Metal Bracelet Sets, $4.80, Forever 21 Floral Wooden Bangle, $8.90


Fendi Folding Ballerina Flats, $340, Stuart Weitzman “Dancercize” Casual Ballet, $230, Steve Madden Keepsake Flat, $49.95