7 Failures Everybody Needs to Have (Only Once)

You got the date! With the sexy, funny guy five years younger! But the two of you made a lunch date, and you're not sure what to wear. You're worried, maybe, that if you dress the way you normally dress—sheath, hose, heels—you'll look too frumpy, too straitlaced. So you stop by a store thumping with music loud and forceful enough to dislodge your contact lens and ask the 15-year-old clerk for something cool and casual. She has just the thing!!!

Which is how you end up walking into the restaurant in an electric-pink jumpsuit with a thick gold zipper that goes from neck to belly button. Does this sound like it really happened? That's because it did, to a wonderful woman whose name will remain unmentioned. Sadly, the pain of watching the sexy, funny guy blink in horror, then put on his sunglasses so as not to be blinded by the fluorescent power of the jumpsuit (which had looked so hip and mod inside the store but, outside, so like a wearable traffic cone) can never be undone. But the takeaway also remains: Dressing has nothing to do with some mythic notion of your being hip or in the know. It has to do with you. Next time, you will throw on that classy, comfortable sheath and stride into the room and look the way you are—sexy, funny and a just a little bit wiser.