After a few months of waiting for, Marc, that cute guy from the legal department to muster up his courage to ask you out, he finally did this morning by the coffee machine! So it’s finally happening this coming Friday. No, it will just be your first date so you probably have to wait a little longer before he introduces you to his parents, silly!

Now comes the hard part: What should you wear on your first date? Yup, this vexing question has been a real problem for women since time immemorial. It may sound like a petty issue for most men, but for all women? The pressure is definitely intense–of course we want to look good (because as they say, first impressions last) but not too much to the point of looking too eager to please. We want to look sexy, but not too much to the point of looking slutty. We want to look comfortable but, again, not too much to the point of looking sloppy.

So how do you go about dressing yourself up for your most awaited first date with Marc?

First thing’s first, you should always consider the setting. Did he ask you out for dinner in a fancy restaurant or for a few shots at your favorite bar? Are you going to watch a movie or will you be watching the Knicks versus Warriors game at the Garden?

The rule of thumb is: let the location be your guide. If it’s going to be dinner, then naturally, you would have to dress up a little fancier. For a fancy dinner night out, you can never go wrong with the LBD/pumps ensemble. It’s provocatively sexy yet classy, and I’m pretty sure he won’t be able to take his eyes off you. Just a word of caution though: avoid showing too much skin—yes it may look sexy but it just doesn’t look elegant. That’s the key here: your dress should be a perfect blend of sexy and elegance.

LBD: Elegant and Sexy
LBD: For Fancy Dates

If he asked you out for drinks, this means he just wants a more casual date and probably wants to know more about you. For dates like these, I suggest going for the jeans/blouse getup or a casual dress. This will help make the atmosphere more relaxed and informal and this will allow him and you to open up a bit to each other.

Jeans and Floral Blouse: Feminine and Sexy
Summer Dress: Hot and Sophisticated


Same goes with movies and going to a ball game, it’ll be much better if you’re wearing a much relaxed getup like a skinny/shirt/jacket/wedges ensemble, if it’s a ball game, much better if you wear your team’s jacket—nothing says fun and sexy to guys than a girl who knows her sports. And instead of wearing heels, you’d definitely want to wear sneakers on a ball game as it’ll be much more comfortable and of course, it will make it easier for you to maneuver your way through the stands.

Wrap-around Blouse and Black Jeans: Chic and Comfy
Sheer Blouse and Denim Pants: Fun and Outgoing


Well, that it! That’s all the advice I can give you. If there will be a second date, it’s entirely up to you now. Good luck and have fun on your date!