I’m often fond of saying that after a certain while, living in New York becomes like living on a Monopoly board: same players, same places, same scene—the only thing missing is the free parking.

I found myself reminiscing about Fashion Week as I exited the cab on the south corner of Bryant Park for my first event on Wednesday evening: the Rachel by Rachel Roy launch and über-private reception in her showroom.

Arriving on the twenty-something floor and walking into the well-appointed and chic showroom space, I almost felt like I was back in the exclusive Mercedes-Benz Star Lounge where many happy memories have been formed over the past three seasons, most involving champagne and celebrities.

My first instinct was to relieve one handsome cater waiter of a cocktail and then scope out the room.  Teen Vogue editor Amy Astley was perusing the collection while Beth Ostrosky Stern mingled with other guests that included Kelly Killoren Bensimon and model-turned-DJ Sky Nellor.  In the back, Alexandra Richards was DJing, playing lots of Cut/Copy and MGMT that put me more in the mood to dance than look at clothes.

I went over to Ms. Roy to ask her about her new collection.  She was imposingly tall with dark, piercing eyes.  “The new collection is a bit younger and edgier,” she said.  “It’ll be sold exclusively in Macy’s beginning in early August.”

My next stop was the Belvedere Black Raspberry launch party downtown in a pop up space created just for the three-night long celebration.  Inside, slogans like “Maceration is perfectly natural” lined the walls.  Confused but intrigued, I had to ask one of the publicists outside what this meant.  Apparently, maceration is one of those words like “jactation” that sounds dirty but is actually quite technical—it refers to some type of esoteric fermentation process that infuses fruit with vodka.  Sexy stuff.

Within the next half hour, nearly everyone that had been at the Rachel Roy presentation was now here, drinking their macerated cocktails (there’s a two-word combination that definitely sounds dirty but isn’t).  Kelly Bensimon was the first celebrity to arrive, carrying the Jonathan Kelsey “Belvie” bag, specially designed for the occasion.  Sky Nellor also made the trip downtown.  “I’m flying out to LA to DJ the USA/Vanity Fair party,” she told me when I asked her what she was up to.

Soon after, the woman of the hour, Estelle, arrived to a flurry of flashbulbs.  “I’m working on my new album,” she said when I finally got my chance to speak to her.   Next up was Erin Lucas from The City, wearing a lace ensemble with Christian Louboutin pumps.  We talked about sudden fame and having cameras around all the time—both seemed quite natural to her.

The next evening all my events were on the same corner of the Monopoly board in SoHo.  Running an hour behind, I headed over to a giant loft for the Serge Strosberg vernissage called “Les Demoiselles de New York” featuring nightlife icons such as Kenny Kenny painted in an expressionist style on a giant tableau.

After a few minutes, I had already rolled the dice and landed at my next stop: The Randolph on Broome for the StyleCaster/Famegame party.  The tiny space filled up quickly—to the point that it was nearly impossible to move—no one was passing go, no one was collecting a cocktail at the bar.  We stayed for a drink and on the way out and once again ran into Erin Lucas as well as designer Keith Lissner (now also a cast member on Bravo’s Project Runway spinoff, The Fashion Show).

We had come full circle when we ended up once again at the Belvedere pop up space for the second night’s party with Out Magazine hosted by Patrick Duffy.  I first said hello to Kenny Kenny who I had just missed at the vernissage before hijacking the passed hors d’oeuvres plate.  Perhaps to escape the monotony of characters that had been imported from The Randolph, I soon turned to drink—a dangerous thing in the presence of an open vodka bar.  Before I knew it, I’d ended up at the unofficial after party at SubMercer, hanging out with a group of drag queens when in walked Erin Lucas.  If one of us owned the properties on which we both seemed to keep landing, the other would definitely be mortgaging Pennsylvania Railroad right about now.

At the end of the day, maybe it’s sort of comforting knowing more or less exactly what’s to be expected with each event—after all, when you take a chance, you might just end up in jail.

Adrien Field