Dressing with a Degree of Difficulty

I don't know if I'd call myself a "fashionista," but one thing I really like doing is coming up with outfits inspired by where I'm going or what I'm doing that day. (I rock costume parties, if I do say so myself.) It amuses me, and in an odd way it makes life easier: having some parameters eliminates the "paradox of choice," you know.

But I just found out that my office's holiday party is going to be held at a tiki dive bar, and for once, I'm at a loss to come up with the perfect outfit.

Let's parse the situation:

• The party is at a dive bar, meaning that it would be wrong to look too fancy, dressy, or "done." So I need to look studiously nonchalant--which is hard.
• It's also a tiki bar, which requires a certain sense of whimsy and lightness. Bright, summery floral prints sound more appropriate than wintry sweaters.
  
• But at the same time, it is a holiday party, which means that it would be wrong to look too summery, as though I'd forgotten that it's December outside.
  
• This is an office party, and I'm the new girl, so I don't want to look too outrageous, or like a floozy. I have to work with these people every day, after all.
• But at the same time, because I work with these people every day, I want to wear something that they haven't seen me wear before--something I probably wouldn't wear to the office.
  

So you understand the quandary I'm in: wanting an outfit that is tropical but Christmasy, distinctive but not wacky, fun but not immodest, relaxed but not staid. If choosing outfits got scored for degree of difficulty, like Olympic gymnasts, this one would be a 10.

And we haven't even touched on the other challenges of my first-ever office party (and first-ever time in a tiki bar), foremost among which will be refraining from singing "Mele Kalikimaka" when I get a little tipsy.

Image of tiki bar stolen from Mead Hunter's blog.