Single or married, like it or not, we’ve all dealt with this issue. You’ve got the guy, you picked the restaurant, but what are you going to wear? When it comes to choosing your date outfit, and especially for those first, crucial meetings, there’s a few simple rules to keep in mind. I suppose it’s just like dressing for any other occasion. You consider the location, the time of day, the company you’re with and the weather. You want to be comfortable but dressed appropriately, though everyone knows that the very first impression can be a deal breaker. So how do you present a version of yourself that reveals just enough to keep him interested, but not too much so to make him bolt the moment you step foot in the door?  It’s all about how you want the guy to perceive you. What do you want to say about yourself? You decide. But if you want him to like you before you open your mouth and blabber about your last break-up you’ll have to put a little bit of thought into the outfit.

1. Show some skin. Whether it’s legs, shoulders, neck and/or arms, men want some eye candy. And most men do like skirts! Though jeans are perfectly fine, if you have the choice, and it’s nice out, go with the skirt.

2. Show a waist, show some shape. Don’t wear boxy T-shirts or oversized jeans. Make sure you can tell there’s an actual female form underneath the fabric.

3. But don’t dress slutty. Unless your intention is to keep the guy in a perpetual state of arousal while you’re having dinner, leave some to the imagination. There’s a fine line between being provocative and being sexy. Outfits that are too revealing can be intimidating, or off-putting, even confusing at best.

4. Don’t wear anything too complicated. Men don’t understand fashion. Start with a simple silhouette and save your fashionable outfits for later, after you’ve reeled him in…

5. Be confident. Don’t lose yourself. If you’re not sure about the outfit, change. If you’re into black, wear it. If you’re a fashion girl, show your colors. You want to be at your best behavior, feel beautiful, comfortable, flirty and feminine. Whether you’re a tattoo-toting rock chick or a spectacled brainiac, boys are impressed by femininity. And if you really insist on wearing sweats and a hoodie, show up with nice hair or some lipstick. Make an effort, even if minimal.

I decided to do a social experiment with the help of Barneys. I applied my handful of rules and chose four different types of dating outfits, each for a special occasion. (You’ll notice in the video that I only wore dresses and skirts. The jeans only come out when it’s cold…!) With the Barneys video crew in tow I took the outfits to the streets of Upper Manhattan and asked a few honorable gentlemen a few simple questions : 1. What is the perfect (first) date outfit for a girl in your opinion? And 2. Where would you take me in this dress? The answers were revealing to say the least. Some of the men had very detailed, pre-conceived notions of how a girl should present herself. They read into your outfit like seasoned critics, eager to pick up on any clues about your real personality and intentions.

And they notice things you would never even think to check, like your handbag for example. One guy said he always sneaks at the bag. “If she’s carrying a Chanel hand bag on the first date, I am putting myself up for disaster. What will I buy her when she’s older? The next thing up is a Birkin bag and that’s just gonna break my bank. If she shows up with a Proenza bag, I know she’s my kinda girl.” So not only did this guy know about fashion brands and their hierarchy, he also made up his mind about how he wants to treat his girl. There’s a plan! When it comes to skirts, the men are on the same page. If it’s nice out, show leg. But not too much! The Irish man said his mom would not approve if he dated a girl who wears short, tight dresses. And the African American man – I told him he should take acting classes and become a comedian – wants his girl to be covered up. “She should be sultry and not show too much. Things have to fit right. Nothing hanging out. Nothing too short.” But in the end it’s all about confidence. If you feel good in your outfit, it’s only going to benefit the conversation. Though you may sometimes feel like you’re making compromises on the outside, it’s only temporary. Your personality will do the rest of the talking.

The mint, pleated ‘cocktail party’ dress by Christopher Kane and ‘Tawaraya’ sandals by Sergio Rossi; The striped ‘lunch date’ top and skirt by Ohne Titel and raffia wedges by Dolce & Gabbana; The black silk embellished ‘fancy dinner date’ dress by Lanvin and black mules by Celine; The green leather ‘seal the deal’ dress by The Row.