Fashion Friday: The What to Wear to the Oscars Episode

In New England, we're loathe to call attention to ourselves. We don't wear pretty hats in the summertime. When black tie is optional, we opt out. We're not a flashy people. As a result, dressing up often means wearing our "good jeans." I know. It's a sad state of affairs. Blame the Puritans.

And while I do envy my southern sisters with their go big or go home sartorial bravado, there are occasions where I think we have a leg up. Ladies and gentlemen, welcome to the whatever-th annual Academy Awards.

I think black tie events, especially black tie events where awards will be handed out and/or rings will be exchanged, require a certain degree of restraint. It's a paradox, I know. But isn't there something awesome about having the confidence to show up a little under dressed, a little tousled, like this isn't going to be the greatest day of your life? Because hopefully it's not. Hopefully there's more to come.

So, in that spirit, I give you my suggestions for divinely dignified Oscar wear. If you're looking for "Old Hollywood Glamour" you've come to precisely the wrong place.

You can't really go wrong with Donna Karan. She understands looking good without sacrificing comfort. And you might as well get comfortable. We're not getting out of here until eleven- at the earliest.

Hey, this is Gaultier is kind of awesome. It's about as fancy as you can get without gratuitous embellishments. Is that redundant? In any case, look how she has to avert her eyes to avoid the glare of too many stars. This New England girl's not impressed; she's irritated that she's going to be stuck in an auditorium with these people for the next three hours.

Pardon me, Sir. It appears as if your date is wandering off. Wow, she really must be bored by this whole thing. Is she from New England? I hear those gals are not into this fancy schmancy stuff.

If you really can't take it anymore, you could always amuse yourself by twirling around in your Carmen Marc Valvo. What? People do that.

Well, but don't let's everybody do it. That would just be crazy. Your Puritan ancestors would not be pleased. They'd throw you in the stocks. Frivolity. Your parents were obviously total failures in raising you.

How about hair and make up? You want to keep it soft and kind of messy. Remember, you're here because you're a good sport. Not because you care. Try any of these looks:

Oh, hey, Steffi Graf. That reminds me. If you could possibly squeeze in a tennis match or something rather then spending six or eightish hours getting ready for your big event, I think that would bode well. I mean, we should be at least as interesting as we are pretty, right?

Here, Sheryl demonstrates what it's like to be beautiful in a casual, non-aggressive way. Don't you get the feeling she's not the kind of gal who talks about people when they leave the room? Or writes things about them on her cheesey blog?

So pretty. I love a dangly earring with no necklace.

But if you do wear a necklace, how about a sweet, pretty one like this? One that doesn't make you look like you borrowed it and, consequently, are being followed around by a troupe of armed guards. Because that is the opposite of casual and nonchalant. And could be an impediment to being approached by George Clooney. You know, should he tire of his whole gorgeous Italian ex-model girlfriend situation.