A passion for food + fashion

Postcards from Billy: High School Reunion Edition

In Fashion on May 13, 2009 at 7:24 am

stampsFor the newly initiated, POSTCARDS is recurring feature with fashion advice from my dear friend Billy, an art consultant with a wicked eye and even wickeder wardrobe. In this edition, he packs his bags for his 20th high school reunion. And for those of you who caught the Gossip Girls ’80s flashback on Monday, the timing couldn’t be better…



2009 has thus far been a year of great indecision. Perhaps the stress at work—I fundraise and the current economy doesn’t lend itself to having your hand out—has manifested itself in not being willing or able to make snap decisions. It took an old friend booking a flight to Atlanta to prompt my attending my 20-year high school reunion. I had been sitting on the fence about revisiting the ne’er do well days of my youth.

If you are of my generation, certain films were so integral to our youth—most of them from John Hughes.  Who could forget Molly Ringwald’s moment getting felt up in Sixteen Candles and that über-cool outfit she wore as Claire Standish in The Breakfast Club? But for this trip down memory lane, I am going to refer to a movie that was slightly post-college, Romy and Michelle’s High School Reunion.  As I contemplate this weekend of seeing old friends and acquaintances from two decades past, I wonder, shall I create a fictionalized version of who I am today? Why dwell on the fact that I am not living in the Park Avenue co-op that I thought I would be in at 38 and instead find myself in a rented Atlanta apartment?  So what if I am not running a successful art consulting business out of a chic Watergate-style highrise.  I might as well dress the part and let no one be the wiser.


My partner in crime for the reunion is one of my dearest friends, Anna.  She was a good girl whom, I hate to admit, I might have turned a little naughty our senior year.  She was a dedicated violinist and took all the AP (advance placement for those who’ve forgotten) classes that were filled with other upstanding students.  A second-generation Swede, she has some funky ABBA qualities that most others from our small town in North Florida lacked.  When we started clubbing, her signature outfit was either a Laura Ashley floral sailor dress with cowboy boots or a Commes des Garcon white button-up shirt (borrowed from my closet) with black mini skirt (a la Robert Palmer “Addicted To Love”) and Joan and David red patent leather Minnie Mouse shoes.


I should also mention that she had enormous ta ta’s, a 36 triple D, and this gay boy was endlessly fascinated by their abilities from purchasing alcohol underage to  catching the eye of many cute college fraternity boys at Florida State. Honestly, some of her choices still make sense today.

On the other hand, my wardrobe generally went the route of oversized Ralph Lauren Polo shirts (remember the year that crests were in vogue?) and baggy jeans.  At least I mixed it up with a great pair of Army Navy black patent leather lace-up shoes.


The daunting task of strategizing the wardrobe for this weekend of fun is now at hand. A little more background on the audience we are dressing for? We graduated from Maclay, a small, private school whose official song referenced sunny plantations found in our neck of the woods.  The year was 1989. Picture a sea of WASPY young faces (being half-Asian, I was the token ethnic in our graduating class) wearing lots of Esprit, Joan Vass knits and Ralph Lauren tartan handbags. Boys in horrible pegged Guess jeans and K-Swiss sneakers.

Here’s what I am likely to throw in my Prada weekend bag and for Anna, since I have not played in her closet for quite some time, I will fantasize of ensembles which would make sense. For inspiration, the soundtrack on Rhapsody: REM’s Superman, PIL’s Rise, Big Audio Dynamite’s E=MC2, Bananarama’s Venus and our favorite song of the time – New Order’s Bizarre Love Triangle.

Pour moi – nothing but the big guns. None of the high-ticket items will be left in the vault.  If you are going home, you might as well be piss elegant – see, I’ve already started affecting the Southern vernacular.  All of the Hermes belts will be part of the arsenal, my brilliant slate gray Prada suit, APC skinny dark jeans, great camouflage Converse sneakers for a little edge and some Brooks Brothers boys tee shirts to show that I’ve not let myself go and to highlight my arms, which I’ve concentrated on of late at the gym.


For my arm candy, Anna, I would recommend: Only 2 handbags for the weekend—an orange Hermès Birkin (orange was her signature color) and the new Chanel clutch with attached coin purse.


Edgy shades for making an appearance for the first day mixer – I really love Moschino’s oversized sunglasses that resemble space creatures from the X Files.

moschinoframesA leopard skirt, Elie Tahari has a nice option, and chic Carolina Herrera men’s style tailored shirt. Since Anna has a great rack, she should wear it unbuttoned with just the peak of a La Perla bra. Since I am suggesting this look for the first evening cocktail reception, I would say go balls-to-the-wall and pair the ensemble with fishnets and Christian Louboutin peep toe stilettos.  She could say she has spending a lot of time at her current beau’s Lake Como home and this appropriate attire.

Christian-Louboutin-Peep-ToeFor the daytime school tour – gotta love Alumni offices shaking you down for money – since she has a great Little Nell bob haircut she should channel a pill popping Greenwich hedge fund manager trophy wife.  Faded jeans with the requisite tear at the knee, beige TSE cashmere twinset with matching snakeskin Jimmy Choo stilettos and lots of REAL jewelry.  Don’t pull out the costume pieces—wear every great piece she’s invested in the past two decades – rings, bracelets and layered necklaces.

For the ode to the prom that most of these weekends pull off tragically – it’s time to pull out vintage from the era.  Since Anna has been ballroom dancing and has a rocking figure, it’s time to find the Lady Miss Kier jumpsuit, wide headband with hair flipped at the ends and platforms.  The au courant Chanel clutch will show that this former New Wave girl is all grown up.

Lady Miss Kier of Deee-Lite

Lady Miss Kier of Deee-Lite

As much as copious amounts of alcohol make sense for this older rite of passage, I have to remember that no one likes drunken stories that start out “remember when?”  Perhaps I will just have to stop at a head shop and buy “whip its” (if you ever spent Spring Break in Panama City Beach you know what I am referring to) or hit-up my shrink for some Xanax to have some sort of foundation buzz.


  1. polo shirts are very stylish and very comfortable to wear during hot and humid weather _

  2. polo shirts are very casual and stylish indeed, most of the time i use polo shirts ,`~

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