Yo ho, ho and a bottle of Tums

So the highly-anticipated Caribbean Casual day has finally arrived…and I am still not exactly sure what the higher-ups were asking for when they scheduled this event. Last time I was in the Caribbean, people were wearing shorts….and we’re not allowed to wear those here, so what do they want from us? I spent the majority of the evening trying to think of what things in my wardrobe would even qualify for this theme day. Eventually I realized that if I was going to go casual, I would have to go out and buy something new….but what? Here are the images that flashed across my mind during the brainstorming process:


Option 1:
Colorful, yes, but perhaps a little much for the office. And really, how flattering can a dress be when it is made entirely of plaid.












Option 2: But then, I don't really look good in vests, so I don't think this will work.














Option 3: This doesn't really have anything to do with the Caribbean-but you have to admire this man's spirit.












Option 4: Arrgggggg matey! Maybe not-plus I don't think I can grow facial hair like that over night.











Well that was a wash, and when it was all said and done, I opted for a business casual ensemble from the Gap. Really, I think this “Caribbean” theme was just a clever attempt by management to see just how far their employees were willing to go to wear sneakers at their desk.

I saw past their clever ruse and the battle is mine! Little Miss Westchester: 1, Company X: 0.