What to Wear: Vintage Cocktail

Christine in Canada (I seem to be getting a lot of Canadian readers lately, which is lovely because I used to have a co-worker who was Canadian and I ardently celebrated Canada Day for many years. Anywho) wrote in with a request for an upcoming wedding:

I have a wedding to attend in September and would like to create an outfit around a 1960s dress I purchased recently. I am at a loss for hair, jewelery and shoes.

I’m the plus-one of a former and possibly once-again boyfriend at his friend’s wedding, for which he is a groomsman. The wedding will be large and traditional and in a hall or hotel.

The dress (very amateur rendering here) is black, with an empire waist, and hits an inch or two above the knee. Both front and back of the boat neck collar are covered in silver sequins, which have a lovely, slightly tarnished patina. The back has a diamond-shaped cut-out, also bordered in sequins, and a bow with long, drapey tails.

I’m 25, 5’6″ and about 110 lbs, slender but curvy (boobs and a butt, skinny arms and not-so-slender athletic legs). My skin is olive, eyes are dark brown, hair is dark brown in a shoulder-length bob. I love heels. I, obviously, love sparkle. And, I’d love your suggestions.

I love wearing vintage! I made an approximation of her dress in PhotoShop and came up with a two sets of accessory options. For either option, she should pull her hair up a la Audrey and rock some 1960’s style eyeliner:

Plan A: Play it Down
Let the dress take center stage with some complimentary accessories. This is a wedding after all, don’t go crazy.
Clutch – Basic black clutch you can find anywhere.
Ring – So, so perfect for this dress!
Shoes – Dark silver satin pumps with a small rhinestone buckle.

Plan B: Play it Up
If you’re going to be fabulously vintage, might as well work it all the way. This is a wedding after all, live it up!
Clutch – Silk and rhinestone clutch from Nordstrom.
Earrings – Big studs.
Shoes – These are so fun! And only $32 on sale right now.

What’s your vote? Plan A or plan B for Christine?