Wednesday, March 25, 2009

the after work date

So tomorrow, the boy I've liked for a long time and I are finally going out. Considering I didn't think he even knew that I exist, this is major. One thing that I have never fully mastered is the art of dressing for the after-work date. Any advice on what to wear? For those of you that are single, what do you like to wear on an after-work date? Pictures are appreciated! I thought about wearing the new Lilly dress that I am oh-so in love with, but tomorrow it will be 48 and rainy. Just what I needed. For cute boy to see me with my hair looking like a giant frizz puff.


  1. I wish I could help... maybe a wrap dress and tall boots?

    good luck!

  2. try its a great place to put your outfit together virtually. I wrote a post about it on Monday. Just wear skinny jeans, flat riding boots, a long-sleeved white tea thats low cut and a black blazer, you will look amazing!! xoxoxo

  3. yeah i heard it's supposed to be crappy tomorrow and the rain is going to come in the evening -- perfect for ur date (not!).
    maybe wear black pants with heels to work with a cute top that you could wear under a cardigan or blazer? then when u go out just take off the sweater/blazer. Or you could wear the black pants with a simple white tee with a great statement necklace (like something beaded from KEP, Jcrew, etc) -- simple but classic
    when it's raining and im worried about a bad hair day i usually put my hair in a pony tail with a head band -- kind of an audrey hepburn look. maybe try that?

  4. Perhaps my failure in the dating scene (and therefore as a woman) is connected to the fact that it never occurred to me to dress for two things at once? I bring garment bags of options to the office and make people choose outfits for me to change into.