Full blast required:
Don't be that lame guy who comes to every themed party wearing a t shirt, jeans, and a I'm too cool to dress up for this look on his face. Use themes to your advantage to compliment your personality (or break out of the mold every once in a while). Just so happens that this was a nautical themed party, and a great excuse for preppy attire and worth mentioning on this blog, but for times like these I say to hell with your sartorial rules and just let loose. Go for fun and creativity instead of trad.
I used Pierce Hawthorne (played by The Chevy Chase) as my inspiration, minus the Ascot / Pashmina Afghan since I didn't have time to find one as cool.
Attached my professional name tag on my captain's hat that I got from Party City. Everyone called me Cpt. ____ Sparrow by the end of the night. I am wearing my old shitkicker Anderson-Little blazer since I didn't want beer spilled on my nicer J.Press one. Ralph Lauren short sleeve pink polo, popped naturally. My Volunteer Traditions state belt since I actually don't have the common nautical flagged ones that every fratter owns but can't interpret let alone know the difference between starboard and portside. Duck Head stone chinos and my sockless Classic Brown Sperrys, not pictured. Test drove my new Smathers and Branson monogrammed flask, which got a lot of approving nods and high fives.
Glow in the dark frogskins for added measure. The croakies prevent your shades from falling into the turbulent water, or in my case, beer. My date / friend / first-mate with matching sailor's hat.
Such a simple outfit got me a ton of compliments. Other guys wore boring swim trunks and flippy floppies, or those flimsy life jackets (was thinking of doing this along with a martini glass too, to satirize the typecast drunken rich yachtsman about to be evacuated, but oh well will save that idea for next time). Most of the girls wore Saint James-esque meridian striped shirts. But no one looked baws like me!
Believe me when I say I f*cked a mermaid.