A while ago, someone wrote in to ask me about advice on dressing for speed-dating. At the time, it seemed to me an easy question. Then I actually did it.
From my own experience and those of my friends, I have gleaned that the following things are specific to the medium and of vital importance. (I mean, not world importance, but as long as we're talking about dressing for speed-dating.)
Neckline is all-important.
You are sitting the whole time. Plus, you will probably be wearing a nametag. Both these things bring your boobs into focus. Practice sitting in anything you wear and see how this effects the neckline. Storytime: I thought a wrap dress would be perfect. I don't know; "speed-dating" somehow said "wrap dress" to me, maybe because I think of it as the "career gal's" uniform and it was an after-work situation. I didn't wear a camisole (crucial error) but I did ply the Fashion Tape. And you know what? I spent the whole evening looking down to make sure the tape wasn't visible, and tugging at my neckline and generally drawing far more attention to my breasts than I would have had I worn anything else. Especially unfortunate as I was there in a platonic, making-new-friends capacity. Oh, and as a result I stuck my name tag way up on my shoulder, where it was obscured by my hair. On the other hand, major boob can be memorable: next to one of the women's names, my friend merely wrote in the notes space, "cleavage."
Set It And Forget It
Yes, this is really the golden rule for dating generally, but especially applicable here: you want to feel comfortable. And after you dress, not think once about what you're wearing. Go with something tried-and-true.
Make sure you're in something you can sit in for a long time: no high-waisted skirts you can't breathe in or jeans carving a wedge into your midsection. Ditto dresses or tops that have an uncomfy tendency to migrate in unflattering ways.
These things often involve mixer portions. Wear shoes you can stand in for the evening.
With this in mind, and with the consult of many a dater, I give you the following getups. The first is a basic: a wrap dress really is a good day-to-evening option, and, with a camisole, both easy and comfortable. It's kind of a blank slate getup — but if you don't want to think about it, a good option.
If you're coming from a job where you can do jeans, the old heels-and-top combo is a no-brainer. Again, make sure the neckline feels comfy and that the jeans feel as good sitting as standing (doubly important as presumably you'll have been working in them.)
And if you're coming from a really officey office? Well, you'll probably be in good company, but it's always nice to try to mix up basic shapes with prints and a cool shoe.