Crisis of the Century

I can't even describe how excited I am for my 5-year high school reunion this weekend (and yes, we do indeed have a five year. since it's a boarding school this is how we get to see each other!). I have been itching to see my friends and classmates and all of the faculty of my fantastic alma mater. 

However, there has been a major crisis brewing for weeks....what am I going to wear?!?!?!

Catalina (my school) is famous for its impeccably-dressed students (or at least I'd like to think so). One of my classmates said it perfectly: "the communion line at mass was like a runway".

When I was 17, on the verge of graduation, I envisioned myself coming back to five year living here:

working here:

And already having won a Pulitzer. 

Things are maybe just a little different than what I would have expected. So I've got a different closet to work with than I originally planned on. Given that, which look should I go for all weekend??

Druggie model in jean shorts?

The classic Jackie O?

Rebel without a cause? (no pun intended)

Eccentric like Iris?

Decked out in jewels like this fashionista? (sartorialist)

Bright bright bright like my Italian style icon Anna Della Russo? (also sartorialist)

Or stick with my original plan, and channel MK all weekend?

Knowing me, I'll probably be head-to-toe in J. Crew all weekend, but I'd like to avoid that. Do you guys have any ideas? Maybe I'll just have to pop over to Village Tailor and Cicada for a little help....