Stilettos V. The Glass Ceiling

Clutching white Ann Taylor swag bags and Starbucks coffees, they stood in tight clusters amid racks of clothes—querying each other by the corals, babbling by the banana yellows.  They erupted in peals of laughter looking at a peacock’s tail of colors: turquoise, cerulean, India green.

“Ladies, can we kinda all gather to the center?” a large bald man yelled, silencing the chatter. He wore a brown sweater vest and a shirt printed with tiny flowers over his self-described “belly.”

Nearly 50 Harvard undergraduate, graduate, and Extension School students crowded around Bald Sweater Vest Flowers, the store manager of Harvard Square’s Ann Taylor and creative director of this night’s event: “Dress for Success (Women).” The show was about to begin.

“You’re never wearing flats to your interview if I have my way.  Never, never, never, never,” said Bald Sweater Vest Flowers. “What’s the ideal heel height to wear?"

“Four inches,” volunteered Kohl Eyeliner Slim Leg Khakis from the audience.

“You’re a saucy girl, aren’t you?” said Bald Sweater Vest Flowers. (The answer was two to three.)

Out: flats, ill-fitted skirt suits, bare legs, red. In: heels, structured blazers, sheer tights, blue.

“There are four elements of style: color, pattern, texture, and shine.” He fixed his eyes on an audience member. “You.” Tiered White Blouse Gold Ballet Flats entered the ring, blushing.  Bald Sweater Vest Flowers pointed out her blouse, flats, black blazer, sparkly gold belt, and opal earrings. “Things that babies like,” he said.  “As adults, we still find those things super, super attractive.”

Time for some practical advice from event sponsor Tweed Skirt Suit of the Office of Career Services: “Never put your name tag on your boob.  Because if someone’s talking to you, where are they looking?”

Blue Jeans Army Jacket won the raffle for a free suit worth about $270, and then it was time to browse with the experts—Tweed Skirt Suit had called tonight a “leave your wallet at home event” despite the 30% discount on most items. Within minutes, Orange Pants and Heaps of Necklaces was adjusting a blazer sleeve for Polka Dot Cap-Sleeve Top.

In the dressing room, Paint-splattered Pants and Plum Lipstick critiqued a look: “I love how it’s like black, black, black, black, and then bam!  The nude heels pop out.”

At a makeup table (brought to you by The Body Shop), Cat Eyes Tool Belt of Brushes held up a blood red lipstick.  “Classics,” she said.

Ann Taylor’s mild soundtrack of indie techno and tables of bangles differed starkly from the equivalent men’s event in Ticknor Lounge, where Harvard gents reclined on chaises smoking cigars, chuckling knowingly as they ran their fingers over custom-made Brooks Brothers suits.

Or so I imagined—the sign-up list for the next day’s “Dress for Success (Men)” was already full.  But after nearly two hours on my feet in Ann Taylor with nary a chaise in sight, I turned conspiracy theorist.  Maybe “Dress for Success (Women)” was another Strategy to Keep Women Distracted While Oppressing Them, like purses or stilettos.

Bald Sweater Vest Flowers, by the way, offered a tip on mastering those pesky stilettos: “You find a classmate who’s transgender.  Those transgender girls, they can walk in any kind of heels.  And they can teach you.”

Maybe Bald Sweater Vest Flowers will find his way to “Dress for Success (Gender Inclusive),” tonight at 6 p.m. at OCS.  Even style gurus have lessons to learn.