A Surprise Dilemma

Issue 1: What to wear to a 'surprise' event when told, in the typical male fashion, to look 'nice'?

Issue 2: So, just how nice is nice?! Are we talking cocktail dresses and 5 inch heels or (I loathe this term) 'smart casual'?

Issue 3: Location- outside or inside? Adequate central heating to render an outer layer negligible, or should one expect the worst Arctic conditions? (And to this point, should I take a larger bag in which to place said cover- up, in case there's no where else to put it?)

Issue 4: What will everyone else be wearing? I am no means a sheep, but turning up in cowboy boots when everyone else is in heels? It's just an annoying loss of the chance to dress up!

Although this unknown event has made me quite speechless with excitement, tonight is going to be a long evening of ransacking my wardrobe to find the perfect solution to my sartorial issues. One thing is for certain: red lips and rails are a must, a la Chanel!

Both images are from Google