What (Not) to Wear?

Posted on by

The organization where I work is having a fundraiser the first weekend of November. It’s a silent auction fundraiser with somewhat of a Christmas theme. I’l be working it, but we’re still supposed to dress the part, i.e. cocktail attire. I’ll be honest, I have NO idea what to wear. I feel like I have a couple of dresses that would suffice if it were a summer evening event, but my thought is it will probably be a bit chilly and I’d like to have sleeves, or at least the option of putting on a sweater. I’ve gotten the sense that the staff wears a wide variety of things, from one person who said she’s wearing a gown to another who said she always wears pants. I think one across-the-board attire item is flats, since we’ll be running around all night, but other than that it’s all up in the air. I’m game to buy myself a new, reasonably priced dress, but I don’t even know where to start! I’d rather err on the side of boring so as to blend in than wear something too unique and stick out like a sore thumb…but I’m also afraid of being too casual. I have a strapless black dress that might work okay, but I’m bad at matching it with a long-sleeved layer. Basically, this is the time when being in my college dorm would be a tremendous boon….but instead I’m turning to y’all in the internet! So…

Help! What would you wear? Where would you shop for clothes for an occasion like this? Pictures and links welcome in the comments!

  • Kyle W.

    I feel like in times like these, I would do the same thing.  I think that any dress that hits you around the knee and isn’t made of a loose jersey cotton would work fine.  Usually when I’m worried about showing off too much skin or worried about it being cold, I either pair a cardigan with it or in the case of a recent wedding, I wore a blazer.  I think if your black strapless dress is comfortable and you have a brightly colored cardigan (red, blue, pink etc) you should be fine!

  • TheGirlintheAfternoon

    What about the bright floral dress you wore for your engagement photos with the purple cardigan you got from Target last week?  Add some dark tights and bright flats.  You’ll look fresh, pretty, and approachable, but since you’re staff, you’ll also be visible to anyone who needs your help.

  • http://www.casadelhansen.com Laura

    What about  your  black dress with some sort of pashmina or paisley shawl?  warm but classy at the same time? 

  • Katie Dornan

    I agree with TheGirlinthAfternoon–add dark tights and bright flats to any dress & it’s instantly “winter” attire

  • Becky

    black dress, black cardigan, pearls and black ballet flats….to be more festive, you could go with a red cardigan, or one with fancy buttons…might be a nice add for your winter wardrobe…could still be very dress with black pants and a camisole under it for other holiday parties….