Winter Sandals

Jenna,

I have a date tonight. I met this girl who reminds me of a young Stevie Nicks. The problem is, she’s from one of those towns in Connecticut where people look at my 2005 Honda Accord like it’s a maroon 1987 Cutlass Supreme.

I think I’ve thrown together a nice outfit, some Nantucket reds (are they still in?), a classy sweater, but when it comes to foot apparel, I’m really leaning towards sandals. I know it’s winter, but my closet consists of the sandals and some old kangaroos?

Amulet Springer IIII
Middle Class Connecticut

Amulet,

Judging by your name, you shouldn’t need any advice in dealing with Connecticut’s old-boy upper crust, but here’s the deal: I could tell you love should be blind to any of these trivial details, but sometimes it takes a little superficiality – and a little style – to get in to the heart of such a woman.

Your reds will be fine, but neither the Kangaroos nor the sandals are going to sweep this girl off her feet. Both, however, may intrigue her. If you can wow her with your conversation, choice of restaurant, etc, then she will see this faux-pah as quirky and cute.

If forced to choose, I would go sandals and make sure to walk through a few icy puddles without a flinch – regardless of how proper this dame may be, every girl wants a little bad ass in their man. Walking through a frigid puddle isn’t the same as say, saving her from a couple of violent muggers, but she might notice it and give you a place to warm those puppies up later on.

Best of Luck,
Jenna