Style Dilemma: Dominatrix Granny

MotorCityGirl emailed me:

Dear DC Celine,

I have fallen in love with a shoe that isn't a flat. It isn't just the name - Eleanora, but I love the way it usurps the classic male wing-tip styling. Maybe it is just that my Grandpa always wore wing-tips, but there is also something about this shoe that says, "I can make it in a man's world while still being a bit feminine."

My question - what should I wear with it? Modern pants suit? Knee-length skirt and sweater?

MotorCityGirl

Dear MotorCityGirl:

First off, these are great! What a fashionable way to tip your hat (or your heel) to your grandpa. Wearing a little bit of someone else is a favorite way to keep them with me.

Secondly, va-va-voom! These are so very, very now, and, as you wrote in my quest for a costume, innocence can be sexy. In between editing sentences last night, I saw what was most likely a re-re-re-run of Isaac, who called similar shoes "Dominatrix." I kid you not.

The point is that these are a grand way to bring a little bit of cheeky femininity into what might be a staid outfit. I think you're on target with both the modern pants suit and the skirt & sweater. What I'd do: add a little bit of flounce to either. Go find one of the long-sleeved ruffled (pick your level of ruffle according to your own sensibility) shirts all over the place right now. Make sure it has sleeves long enough to peek out from underneath your suit jacket or sweater. For medium spending, try Ann Taylor's Ruffle Shirt. If you don't want to spend the 70 bucks, go for WalMart's (yup, you read that right) White Stag Romantic Blouse at a mere 15 smackeroos. Or, if you're feeling the need to treat yourself, go for broke (literally) with Theory's Nehru-Collar tuxedo.

And don't forget the jewelry. I'd pile it on in a no-nonsense, unabashed reminder of your sex. Boys just really don't wear (or shouldn't) loads of chains. But keep in mind Coco's rule of thumb: Put it all on, then take one piece off before you go out the door.

Make sure you tell us what you do! But before that, tell us whose they are, so we can all run out and copy you.