So I borrowed a wig, big sunglasses, and a scarf from my friend Natalie, who likes to play dress up more than any other adult I know, and tarted up a little sugar pumpkin.
To make your very own Jackie O. Lantern, you will need:
Big sunglasses. It's all about the sunglasses.
A long brown wig
A sugar pumpkin. (Note: take the sunglasses with you while pumpkin shopping. If the glasses fit around the pumpkin's girth, you've got your pumpkin.
Some sort of carving instrument, like a small, sharp knife.
A spoon
A votive candle
A vintage scarf. (Purely optional, but it does complete the look. Pucci's nice.)
Preparation:
1. Cut out a lid on the top of the pumpkin at a 45 degree angle so that the lid will remain in place when pumpkin is hollowed. This opening should be just large enough to allow access to your clenched fist. The smaller the hands, the better.
2. Scoop out seeds and stringy bits of pulp from the inside of your pumpkin with a spoon, preferably made of sterling silver. It's even better if you are using a dessert spoon that has been stolen from the Plaza Hotel in New York. Since I have no such spoon, I had to settle for one I stole from the Algonquin Hotel instead. I am not advocating stealing-- I was just pretending I was Robert Benchley and was therefore necessarily pickled. Reserve the pumpkin seeds for later roasting, since the seeds of the sugar pumpkin are the best for toasting, which is something I learned from Elise Bauer's always helpful Simply Recipes.
3. Situate sunglasses onto the face of the pumpkin to determine the best placement for the eye holes. Cut out small holes with the tip of a sharp knife, then enlarge the holes with the same, stolen silver spoon you used to scrape out the pumpkin's insides. (Note: Holes should not be larger than the sunglasses.)
4. Put your now-naked Jackie O. Lantern upon some sort of pedestal (I used one originally intended for cakes) which, now that I think of it, seems entirely appropriate. Dress up your pumpkin doll with wig, sunglasses, and a purely optional scarf-around-the-neck. Presto! You've got an international woman of glamour sitting on a cake stand in your kitchen.

Lighting Jackie's Fire
To add an inner glow to your Jackie O. Lantern, remove the wig and lid from the pumpkin, place a votive candle inside her, and light. Replace lid and wig. Adjust hairstyle, if the need or desire arises.
For a delicious bit of added fun, summon the spirit of Aristotle Onassis with the help of your Ouija board. Once you have his full attention, blast a Maria Callas aria from your surround sound speakers, then sit back and feel the tension. Voi lo Sapete from Mascagni's Cavalleria Rusticana would do very nicely. I recommend hiding all valuable, breakable objects.
I do not recommend leaving your Jackie O. Lantern burning with fire from the inside unattended, unless you wish to melt your wig or set your house ablaze, but lighting it does make her eyes shine bright and wide, which makes sense, if you think about it:
That woman saw things that no woman should ever have to see.