5 Simple Rules on What to Wear on a First Date

A first date is not the time to experiment with the latest trends, but trust your gut if you want to. You probably want to wait a minute before you bust out in a full runway lewk, but if this date eventually blooms into a relationship, it should be clear that you wear what you want because you want to. Don't dumb down your style for a stranger, but simplify your favorite silhouettes. For the off-the-shoulder top, we suggest the style that has detached arm sleeves, not the elasticized neckline. The silhouette is notorious for popping up toward your collar, and you don't want constantly readjust it throughout the date.

Pixie Market White Side Tie Linen Top, $89; pixiemarket.com

H&M Shaping Skinny High Jeans, $50; hm.com

Jennifer Meyer Large palm Tree 18-Karat Gold, Diamond and Turquoise Earrings, $4,000;

My rule of thumb is that most first dates do not require a heel (it's also easier to gauge your height differences in flats). If you feel uncomfortable wearing an outfit in your own home, chances are you'll be tugging at your clothes all night long. A pair of platform espadrilles are perfectly acceptable, especially if the date's activities are a mystery and you end up on your feet for hours at length.

Chloé Tie-Neck Denim Blouse, $695; matchesfashion.com

Whistles Made Birds Nest Hoop Earrings, $38; whistles.com

Topshop Crepe Pocket Mini Skirt, $66; topshop.com

Carole Shashona Tennis Bracelet, $7,900; barneys.com

Soludos Leather Platform Smoking Slipper, $99; soludos.com

You don't want to step into a jazz club va-va-vooming like Jessica Rabbit on a first date, but you don't have to dress like a prude either. Toe the line between sexy and boring in a slip dress, but tone it down with casual accessories. Wear a pair of statement earrings to add some interest to your outfit, and they can be a talking point if conversation dies down.

Organic by John Patrik Bias Long Slip, $189; organicbyjohnpatrik.com

Of Rare Origin Ruby Aviary Classic Earring, $1,450;

Much like life itself, you don't want to overthink it and complicate your outfit with un-necessities. You can even go straight to your date from the office in this outfit—just leave your jacket at the office. The elevated details on the simplest of work wear—a tank and a black skirt—is just the ticket to go from the board room to happy hour.

Mango Jacquard Cotton Jacket, $60; mango.com

Zeus+Dione Cutout Metallic Trimmed Silk Camisole, $45; net-a-porter.com

Zara Wrap Skirt, $70;

If you can't decide what to pick, just wear your absolute favorite items. You'll feel more confident in something you already know and love, and right now we're loving Aussie brand Réalisation Par. Their flirty dresses are our new summer go-to, and your next first date frock.

Réalisation Par The Valentina, $180; realisationpar.com

Jacquie Aiche Mini Butterfly Stud Earring, $625 (sold individually); jacquieaiche.com

Mansur Gavriel Circle Bag, $995; mansurgavriel.com

Tory Burch Disco Sandal, $262,50;