How Do I Look in This? And This? And This?

Today we’re tackling my favorite kind of shopping. I’ve been invited to—bless the patron saint of satin clutch purses—an Event. This particular event is the Friends of the Library’s 50th Anniversary Gala, a night of literary revelry, and what writer doesn’t want to be surrounded by book lovers?

But it was the prospect of finding a gown that sent shivers down my bookish little spine.

My wingman: Montese Crandall, high school buddy, style maven and fellow Neapolitan. Crave honesty while shopping? Bring a pal from high school. They take great delight in pointing out that perhaps you’d rather go for something with a sleeve to cover that burgeoning underarm swing.

We start at Taffeta in The Village on Venetian Bay. Sheila greets us cheerfully as we haul open the door, decorated with a heavy, metal, floral sculpture. Montese and I agree that we need to work on our upper-body strength. Luckily, Sheila shows us a variety of lighter-than-air confections, and, as we choose, she explains that Taffeta’s owners stock the shop from buying trips to Europe. I mourn that I have clearly chosen the wrong profession as I enter the fitting room.

I try on a black-and-white Peter Martin gown, a halter dress by Joseph Ribkoff, and a jumpsuit (a formal jumpsuit!) with a chiffon overlay by Janine, which nearly makes me declare success right then and there.

But there are too many other divine shops to explore. After working up an appetite opening the Taffeta door to exit, we settle on Campiello’s for lunch. I have the obligatory chicken and pear salad, and, fortified, we waddle next door to Marissa Collections.

Jitka, with a bright smile and intriguing accent, leads us through the massive space. The perfect hostess, she asks questions along the way, and makes sure we don’t get lost near the selection of Jimmy Choo shoes my friend can’t stop fondling.

Montese tries on a stunning black Alexander McQueen (which I try to talk her into wearing every day for the rest of her life), a tomato red Vera Wang and two black Alberta Ferrettis. The latter are not made for Montese’s figure, and we dissolve into giggles as we try to wrangle grown-woman breasts into dresses apparently designed for a nine-year-old boy.

Soon, the newly renovated Waterside Shops are calling, as is a Bloody Mary at the Silver Spoon Café. We sit at the bar and Kate, a charming Detroit transplant, makes mine extra spicy, earning bonus points when she’s quick on the draw with my beloved Worcestershire sauce.

Three ladies at the bar, flush and chatty with afternoon wine, are surrounded by shopping bags. Just a glance at their purchases exhausts us. But as they leave, one of them throws down the gauntlet by asking her companions where they should go next. Never able to back away from a challenge, Montese and I settle the tab and forge ahead to Saks Fifth Avenue. We each find three dresses and are, oddly, placed in the same fitting room. I decide that it’s because I look young enough to be Montese’s daughter and have a grand time goading her about it.

I am punished for my behavior when two Reem Acra gowns—sporting multiple zippers that require more brain cells than my Bloody Mary just casually destroyed—flummox me. However, when we do figure them out, well, let’s just say I am now a believer in the multiple-zipper theory, which is a bit like string theory, only more complicated.

We move on to our final destination, the Caché and Caché Luxe shops. Joan, bejeweled and Florida friendly, places us in (separate) fitting rooms. Two size-four dresses don’t zip all the way up, and I wonder where those "vanity" sizes people complain about are when I need them.

The others fit, and a black Caché Luxe with multiple pleats gathered with a rhinestone buckle, makes me feel like a goddess. Unfortunately, my friend discovers the same dress, and we wind up at the mirror side-by-side, generously insisting that the other looks better in it.

When I drop Montese off, we’re more tired than women in their 30s should be, but are pleased with our day, despite the fact I’ve not managed to make a decision. The formal jumpsuit is calling to me, but I’m also considering a major breach of shopping pal etiquette by sneaking back to Caché Luxe for the goddess gown.

Of course, as any power shopper worth her platinum card will tell you, the joy is in the hunt itself, and I still have some time to explore. If you’d like to know what I finally settled on, you’ll have to attend the Friends of the Library Gala on Dec. 2. If you see me, tell me that you loved my book, or, if you can’t manage that, at least tell me that you love my dress.

Kristy Kiernan is the author of Catching Genius.

The Contenders
Taffeta, The Village on Venetian Bay
Black and white Peter Martin, $425
Black Janine jumpsuit, $310
Cream and black Joseph Ribkoff, $419
Marissa Collections, Third Street South
Black Alexander McQueen, $1,480
Tomato Vera Wang, $595
Black beaded Alberta Ferretti, $3,995
Black chiffon-sleeved Alberta Ferretti, $3,865
Saks Fifth Avenue, Waterside Shops
Bronze Reem Acra, $2,640
Black Reem Acra, $2,300
Gray/brown Melinda Eng, $854.90
(on sale)
Caché Luxe, Waterside Shops
Black pleated Caché Luxe, $278