How to Dress for an Art Event

Let's start simply, with the Saturday gallery stroll. Going into galleries—quiet, expensive, oozily cool—can be intimidating, especially as people who work in galleries are always terribly well dressed. Here is an outfit demonstrates two important Art Dressing rules. First, wear a conversation starter. This dress is Mother of Pearl, which is designed by Damien Hirst's former spouse, Maia Norman. Now you have everyone's attention, because you've said the "e" word: ex-wife. Second rule: always try to incorporate as many jungle animals as possible. I am wearing a lion necklace. Finally, note that I look bemused. Wear a face that suggests, "As of a few days ago, I have seen it all, and the world is now my bemusement park."

Of course, if you're going to a gallery opening, the game is different, though the rules still stand: conversation starter ("That's a lot of pink!" anyone with half a brain could say to you, thus earning you a new friend with half a brain or, if you're lucky, two new friends who have a whole brain between them) and jungle animals (small fish are swimming around on my shoes!). But since it's night, you have full permission to get weird. This skirt looks like a costume from a sea punk production of Gone With the Wind, and, generally speaking, I look like a cartoon character who recently emerged sartorially scathed from an encounter with a steamroller.

If heights don't give you nosebleeds, you may someday find yourself at an uptown gallery opening where everyone wears suits made of the children whose Princeton degrees didn't quite pan out (except at Venus Over Manhattan, where the previous outfit might just pass muster). Find the silkiest, most bathrobe-like thing you own—here, I am wearing a kimono, silk slippers, and carrying a purse made of trees. Then, to transform this from boudoir to bourgeois, think to yourself: your presence makes everyone in the room feel as though you might disinherit them at any time. Even if they are not included in your will. Even if you don't have a will. You have a receipt from Biscuits & Bath, and that is testament enough.

Now let's say your friend invites you to some razzle dazzle invite-only salon. I'm certain you have a wacky coat that matches only two things you own, and this is the time to show off your wacky coat that matches only two things you own. Forget those two things you own, and instead wear your coat with a few printed things in the same general color family. Pretend you match. Try to look like you have no idea what is going on, because if you are anything like me, you never have any idea what is going on.

Now let's say for some crazy reason you're going to buy some art. The key look here is Insane Mom. Remove the jungle animals, and replace the lost sense of whimsy with a suit in an absurd color scheme. You need to project a sense of the rarefied; look for something that suggests you've just returned from taking communion on the moon.

Of course, if you're making your purchase on Amazon Art, ditch the fancies. Art Casual isn't just any old casual, though, so make sure you have a paisley silk pajama set on hand to ensure that you're writing those Amazon reviews in style ("A KINDERGARTNER could make this," you'll opine, "but I can't help myself! I love it!").

Now that you own some art, you may feel you like it so much that you'd go to a whole party for it. Getting dressed for a benefit, like the art groupie summit the Whitney calls its Art Party, say, or something fanciful at the New Museum. Never has the Get Weird rule been more important: I am wearing pants underneath a dress. That being said, if you obey all the rules, all you will never get a t-shirt about missing all the fun. So, you know, it's still a dress. But let's be real: this dress is really a trash bag with a diseased growth on it. And speaking of disease, my purse is a cane toad which has been dyed Schiaparelli pink and had its eyes replaced with Swarovski crystals. Bonus points for a jungle animal that is also a conversation starter! In some intergalactic way, this trash bag/dead toad outfit screams DIY.

But then, what do you wear to an uptown benefit? A tuxedo, of course.