Want to Throw a 'Gatsby' Flapper Party?

But look closely at all these outfits. Doesn't all this frippery look really uncomfortable?

Gatsby is so romantic, right?

OK, well spats look ridiculous on everyone; let's start there. At the Lighthouse Organization's Posh Affair last Thursday, a decorator I really like had on a white and brown pair of Oxfords, and I couldn't stop staring at his feet. And not in a good way.

And the music from the era is great fun—for about 10 minutes. And it's not jazz. Anyone who has sat through the insufferable one-note theater musical The Boyfriend can tell you that all '20s songs sound the same, and the droning on the trombones can be a real headache.

The look is really hard to pull off, especially for women, and a costume party that doesn't make women look and feel good has real starter issues. You have to be bone thin, and willing to wear a ton of makeup that—once the dancing starts—tends to melt. And a giant marabou feather strapped to your head on a beaded choker might look alluring, but have you ever tried one on? It's both uncomfortable and distracting.

I’m not even going to touch the bathtub-full-of-booze concept.

There is a right way to throw a flapper party, and Juicy Couture did it for the first (and what should have been the only) Fashion's Night Out. Juicy hired about 20 actors, who came in full costume. Periodically, they would swarm the dance floor to do the silly period dances, with all the hand swinging and stuff which is great fun to watch, then they went running out onto Fifth Avenue blowing whistles.

Meanwhile, the rest of us got to enjoy the spectacle with the humiliation of participation discarded.

There is one main reason that Nights of the Caribbean parties are doomed to fail: location, location, location. What makes a Jamaican night so fabulous is that you are in Jamaica. The soft fragrant breeze, the lapping of the waves—no amount of pink lighting and umbrella drinks can conjure that.

It is amazing to me that people think of carting sand to a party. It always looks dirty (and never gets fully swept up; venue-owners beware!).

I love steel drums; when we were kids, my parents used to take us to see the Esso Steel Band, who miraculously always seemed to be on the island we were visiting (until I figured out there were a dozen of them). Sadly, when Esso became Exxon, the music died. And now no one can seem to find a real steel-drum band, and piped is simply not the same thing.

All of the sugar in the drinks gives guests a hangover, and the vibrant hues don't look so great on your shirt the next day. And I never really get why anyone thinks it is okay to strap on a grass skirt over regular clothing, do you? The only thing worse is seeing western undies peeking out.

I just groan whenever I arrive at a casino-themed affair. There are so many chores! First, you have to buy some chips after the measly amount they give you gets lost in five minutes. Then, while you fiddle with your paltry pile at the blackjack table, a really pushy couple has already gone and cashed in all their chips and won all the best prizes, leaving you with a choice of colored glass vases or an electronic scale. Casino night rewards selfish behavior, and that is a party don't.

Also, there's all this endless shuffling around, going from station to station, wondering if the next one will be more fun. Turns out losing at the roulette wheel is no more fun than pretending you remember the rules of Texas Hold 'Em.

So then you decide to opt out of the whole gambling thing—but now what do you do?

I always love the story about the sales meeting—I think it was for Teen People—when they hired "bandits" to surprise people on the bus as a way to announce the evening's premise. One lady, convinced by the ruse, swallowed her diamond ring to prevent it from being stolen.

But that’s the problem, isn't it? Isn’t the whole Wild West theme built around the idea of crime and gun violence? And the only interesting outfit choice for women is bar floozy. Nobody wants to dress up as Laura Ingalls. For men, the chaps and holster thing can easily veer into Village People territory—not that there's anything wrong with that. In fact, as I think about it, Wild West is a great theme for a gay sex party.

First of all, the music is great. Second of all, it is so easy. All you need is a DJ and a disco ball. Nobody really remembers what disco fashion was, so just about anything goes, which means no special shopping for guests.

And there is no such thing as disco food, so you're not stuck. Just take it easy on the vinyl record thing (no, it will not be cool to serve appetizers on one).