StyleHiving: A Frisky First Date Ensemble

So, it’s Friday night and the cute guy you met at a party last weekend asked you out on a date — you really like him and really want to overcome all the first date barriers to score an ever so elusive second date. Well there are lots of precautions to take to get there, but I will help you out with the first, which is perhaps the most important. You guessed it: Wardrobe Choice! Since this is a first date, let’s consider a standard scenario: dinner at a restaurant whose ambiance falls somewhere in between local bar and 5-star hot spot, followed by a movie. The combo-date will give us a lot of leeway to examine several possibilities. Let’s look to Cameron Diaz for inspiration.

You could wear that killer dress that never fails to get heads turning. In this situation, however, a dress can potentially make you seem high-maintenance; while some guys do find high-maintenance gals appealing, it’s a slippery slope, and a risk simply not worth taking on a first date. Slipping on a smashing dress, especially when combined with pre-date excitement, can also lead you to go way overboard with the hair, makeup, accessories, etc. — in which case you will have graduated from “too high maintenance’” to “total freaking drag queen”. FYI, that is a major first-date DON’T!

You also could go the casual jeans and t-shirt route, you know, to show him that you’re one of those cool girls who isn’t obsessed with her appearance. Okay, true, he may find your laid back vibe appealing, however, if you put so little effort into this first date, it might make him too scared to stick around and see what future dates might hold. In other words, visions of unshaved legs might send him straight to the island of lost men. Let’s talk about smart options, after the jump.So now that we’ve covered the possible detrimental impacts of going too far and conversely not going far enough, let’s find a happy median. My best advice is to find a balance of effortless, but not lazy; chic, but not too contrived; sexy, but in a way that seems unintentional. My winning formula is simple: dark jeans (fitted, but not suffocating), a flirty top (I said flirty — this does not mean clubby. If it’s a shirt you’d wear to Marquee as a surefire way to skip the line and cover charge, it is not appropriate!), a classic blazer (hip, not business-y), and knee-high boots (excluding vampy stripper boots, of course).


Mint by Jodi Arnold ($154), 12th Street by Cynthia Vincent ($87), Marc by Marc Jacobs ($228)


Development ($328), Iisli ($398), Lux ($39)


BDG ($49), J Brand ($160), Paige Premium ($169)


12th Street by Cynthia Vincent ($359), Aldo ($220), Steve Madden ($199.95)

Check out plenty more frisky fashion coverage over at StyleHive!

Tags: first dates