#454: The Expert

March 23rd, 2015

She wasn’t so much sexy as stylish. That’s the characteristic I figure they hired her for.

Some people can be decked and drizzled with the hautest of coutures and step out into the world looking like a kid in a Halloween costume.

The Gucci, Versace, Dolce and/or Gabbana fits and clings in all the right places, the heels lift asses and the suitcoats hide beer guts just as well, but there’s something awkward and wrong, a plaint in the eyes crying for socks, Crocs and an oversized T-shirt advertising their favorite sports team.

But not her.

She — and the similarly stylish woman 20 feet farther along the Macy’s wall, and the young man another 20 feet away who made a bow tie and sweater vest look like something people outside of a 1940s “Archie” comic would wear by choice — looked comfortable and confident and sleek as a panther in high fashion.

For her, high fashion was pants suit, heels and massive, forehead-obscuring, Jackie O-sweet-Jesus-those-are-big-sunglasses sunglasses. Somehow, she made it work. She looked natural and confident in the swarm of 21st-century “At least I’m wearing pants” unstyled Chicagoans hustling up and down State Street at 5 on a Friday.

She, the woman 20 feet down and black, gay Archie each were laden with a dozen or so purple gift bags.

“Excuse me, do you want a free gift bag?” she called after each woman she saw.

It was a loud but listless call, no intonation between the words. Ex-cuse-me-do-you-want-a-free-gift-bag-ex-cuse-me-do-you-want-a-free-gift-bag. A few steps in the highest of heels toward each of the sweatpant-wearing, scuff-sneaker women she saw.

To a woman, at least in the brief window I saw, they each held up a hand to let her know they weren’t interested. The highest of heels stepped back toward the Macy’s wall, listlessly waiting for the next refusal.

“You’ve got to approach them!” a voice yelled.

The woman looked around, the massive size of her sunglass lenses and the cocking of her head momentarily reminding me of a praying mantis.

You’ve got to approach them!” the voice repeated.

The woman looked around again, this time down. Hunched against a short fence blocking off some grass by a subway entrance, a street person sat with a two-week body funk, a cardboard sign asking for help and a massive grin peering through a beard and unkempt fro.

The two looked at each other, a happy glint in the homeless man’s eyes as he prepared to tell her the secret.

I was traveling at a good clip for a scotch with a friend before heading out of town, so I didn’t catch the end of this exchange. I don’t know what advice he gave, or if she simply looked away, pushing him back in the realm of the invisible.

But for a moment, they connected, the fashionista and beggar. For a moment, they were teacher and student, he guiding her in the subtle art of working a Friday night crowd.

Comment on this story

More high fashion from a lifetime ago

What's this?

You are currently reading #454: The Expert by Paul Dailing at 1,001 Chicago Afternoons.

  • Get Stories by Email

  • Chicago Corruption Walking Tour

    Join the email list for tour dates and info.