Let’s party! Or, to be more specific, let’s take a look at a few of the most fashionable parties ever thrown. You know, the ones that those in attendance still light up about decades later. The ones for which people spent weeks picking out the perfect outfit. The parties that produced iconic images of their time and some which continue to do so. Forthwith…

Diddy’s White Party.

Say what you will about the guy (cough -can’t rap- cough), Diddy throws a darn fine party that turns out some of the fly-est fashions around. And the catch? EVERYBODY has to dress in all white, from head to toe. That’s right, Diddy’s annual Labor Day “White Party” is still one of the hottest tickets on the east coast. And yeah, I know, he’s wearing a gray tie, black shoes and off-white Tom Ford sunglasses in the pic to the right (it’s not from one of his parties) but check out that white pinstripe suit! The man can dress. And he gets hundreds of rich and famous guests to dress according to his wishes, too, if only for a weekend. Now that’s power!

The Met’s Costume Institute Gala.

At perhaps no other event would the Viktor & Rolf dress to the left look as appropriate as at this annual celebration of style. While the frock was generally mocked (at best) or completely panned (at worst), somehow Karolina Kurkova manages to pull it off at the Gala; in fact, her “dates” for the evening were Viktor Horsting and Rolf Snoeren themselves. I really do think she looks fantastic here.
Innumerable other models, designers, actors, celebrities, and members of the fashion elite flock to this event, which often showcases some of the most outrageous looks straight from the catwalk. Every year’s event has a different theme and this year’s May 5th event is “Superheroes: Fashion and Fantasy,” in conjunction with the Costume Institute’s spring exhibit. Giorgio Armani is serving as honorary chair, while George Clooney, Julia Roberts and Anna Wintour are the cochairs. Can I still get tickets? Hmmm…prolly not.

Chicago Playboy Mansion Soirees.

The Hugh Hefner of today (think “Girls Next Door,”) is but a pale imitation of the sophisticated gentleman who threw elegant parties as the original Playboy Mansion, at 1340 State Parkway in Chicago’s Gold Coast. The men were dressed to the nine’s, the women were dressed…barely. And everybody had a swinging good time. These parties set the stage for a revolution in home entertainment: you could stay in and still have a stylish get-together with your closest 200 or so friends. Fabulous!
The pic to the right is from the late1960s/early 1970s – check out the hair. Nice. But what I do love is how everyone’s totally dressed up (I would kill for one of those patterned shift dresses or empire-waisted minis!) and accessorized to the max. Over the top? Sure. But evocative of that time and place? Perfectly.

Truman Capote’s Black and White Ball at the Plaza Hotel.

Many have lauded this as the “Party of the Century,” and maybe it was. This masquerade ball – thrown in honor of Washington Post publisher Katherine Graham (pictured below with Capote himself) – was the event of 1966. Party goers were the creme de la creme from all parts of society and everyone dressed to impress. The funny part, though, was that with the masks, one couldn’t necessarily identify just who was who. What a fabulous conceit! Suffice to say that photographers and attendees alike were taken aback when they arrived. And do you know that Frank Sinatra and Mia Farrow were newlyweds at that time? The attended together, as you can just make out to the right. Don’t you just love Farrow’s simple white dress? She always looked so fresh and gamine.

And I’m totally digging Katherine Graham’s coordinating mask and gown set. Can’t quite tell what those are (beads? gems?), but I’m sure that mask is heavy.

Does anybody throw masquerade balls anymore? I’d certainly go to one. I wouldn’t even have to do my eye makeup! But what about the glasses? Hmmm….