Sadie Stein of Jezebel offers great advice on what is possibly one of the most nerve-wrenching outfits ever planned out: the first date outfit.
...whether you're trusting a friend, compatability points, a promising chance meeting or just fate, we all need to go on first dates sometimes, and it's generally advisable to wear clothes. I polled a lot of friends on this issue and came up with a staggering array of approaches, from "I'll wear my vintage majorette costume and if he doesn't like me for me then he's not worth it anyway!" to "I always buy a new outfit." Most of us fall somewhere between the two, wanting to look attractive but not trying too hard, hoping to balance expectation with excitement.
This should, I hope, go without saying. Painful shoes and jeans that dig into your stomach are not sexy. You want to be able to walk, sit, and eat without thinking about it.
Look Like Yourself.
Another "duh," maybe, but a first date is not the time to try out a new persona, no matter how cool Brigitte Bardot looked in Contempt.
Bring A Sweater.
You might get cold.
Oh, and Practice Sitting Down.
Some things get really low-cut when you're sitting. This can be awkward. You'll end up tugging at your neckline. Trust me on this one.
Have a "Confidence Soundtrack."
No joke, I have a playlist on my computer entitled "Confidence Dressing." It's what I play when I'm feeling shy and apprehensive and need to amp myself up. I always play "I Touch Roses" by Book of Love last, so I feel extra-sassy when I walk out the door.
Personally speaking I've had my fair share of unfortunate 'first date' outfits. During one particularly ill-fated night out I decided to wear Spanx (the gold standard of "supportive undergarments") under a dress. Forgetting of course the part during the date where, you know, you sit down. So, as I'm getting into the car I begin to realize that my dress is significantly shorter than the BEIGE-NON-SKIN-COLOUR-BUT-SUPPOSED-TO-BE-SKIN-COLOUR-OH-GOD-EVERYONE CAN SEE-spanx. So yeah, definitely do the "practice sitting down" one before leaving your house.
Good luck on your date!!