My brother Diego is smart, successful, charming, and chicks think he’s handsome. What some people might not know about him is that he possesses a particularly nasty, cutting wit. If he weren’t a news segment producer, he would have no problem finding work writing barbs for the Worst Dressed pages in celebrity magazines – so keen and unforgiving is his attention to detail. As a boy, he immediately picked up on all of our family friends’ quirks. Thanks to Diego, my Tia Rosita’s mumbling and moustachioed second husband will forever be The Swedish Chef to me. Likewise, it was Diego’s fault that my parents and I could never again look at their friend Giuseppa after Diego pointed out her slightly wobbly right eye.
“Look at it next time,” he’d say. “It’s as loose as a turd in a punchbowl.”
Clearly, he should have been the writer – not me.
One by one, the people in our lives unknowingly fall prey to Diego’s cruel humor. He’s always the first to notice when something is amiss, and when he combines his wit with his powers of persuasion, an object or facial feature is forever ruined for us.
Recently, Diego has turned his powers of observation to fashion. Hounded by the epithet “metrosexual” since his teens, Diego makes no secret of his appreciation for style. He also makes no secret of his disdain of my own attempts to explore it. Let me elaborate: if Diego is the style hound in the family, I am the bargain hound. Lately, while scrounging all of my earnings for graduate school, I’m even more of a bargain hunter than usual. Yet, 2 years of living in Japan and hating Japanese fashion has made me desire new clothes more than ever. I badly want to wear something new, and I badly want my new items to be appreciated. If my brother should be the one admiring something I’m wearing, I know I’m on the right track.
The other week, I went shopping with Momo. While I’ve never been much of an impulse shopper, Momo is the one person who can inspire me to pick up something new without stalking it first. That particular afternoon, a sunny yellow headband adorned with matching covered buttons caught my eye. It seemed impossibly cute and Momo agreed. Since it was only $3, I figured I couldn’t lose. I squirreled it home, excited to show Diego my new purchase. It was the first new thing I’d bought since arriving home in New York.

Eventually, Diego came home.
“Would you like to see my new headband?” I asked, bursting with pride. I had loved the way the yellow looked against my dark hair in the store and pictured myself wearing it with a black shirt. In my vision, I was rowing a boat across the pond in Central Park, my hair was wavy and my wide smile was slicked in a coral-hued lipstick I had yet to buy. I presented my new bauble to my brother, who examined it diligently. I beamed, awaiting his verdict.
“Nice. Real nice, sis.” sneered Diego. “Wow. You know what that headband looks like? It looks like the chit that people can’t get rid of, and then they combine it with more chit to create … even more ridiculous chit!”
“You don’t … like it?” I asked weakly. I sat, heartbroken – my lovely headband threatening to slide from my grasp.
“Come on, sis,” said Diego callously. “You know better than to buy chit like this. It’s like a cross between Mary Poppins and Curious George.”
And just like that, my lovely new headband was ruined. Each time I tried to put it on in the following days, my inner voice crooned lyrics about feeding birds and flying kites. After a week of attempts to wear it, I gave up and banished it to the far rung of my accessories holder.
A couple of Sundays later, I met up with Diego and Joy for brunch and ended up tagging along with them to Bloomindale’s. They were headed to a black tie wedding in Greatneck that weekend and they both needed shoes to wear with their fancy ensembles. Joy quickly found a pair of very beautiful black pumps that even Diego approved of. That done, we perused displays of clothing and shoes to hunt for Diego’s own items. As we looked, he delivered his typical sharp, short edicts any time an offending item caught his eye.
A pair of strappy, flat leather sandals? “Hi, Sister Roberta.”
An A-line fringed blue dress? “Who disemboweled Cookie Monster?”
Diego left Joy and I in the shoe sale while he browsed menswear. I browsed through the 3 pairs of size 5s and Joy was smitten by a pair of flat, black, gladiator sandals. She fell even more in smit with them when she tried them on and we waited for Diego to return so Joy could show him. Beaming, she bounced in her chair.
“I love them,” she said. “And I know Diego will love them, too!”
When Diego finally returned, Joy thrust her sandaled feet in his direction to best show off the shoes – so sure that his face would melt in a smile to match hers. But my brother’s face remained cold and slack, flexing only to curve into a judgmental grimace.
“Baby,” he said. “They’re okay. Too much hardware. They fit funny – like Spartacus’s cobbler was blind in one eye. I don’t know. And you just spent however much on those other shoes for the wedding!”
Joy’s face crumpled.
“You don’t … like them?” she shrunk into her chair, deflated. “I really thought you would.”
“Well, I’m sorry,” scowled Diego. “But they just don’t look worth the price tag.”
As I watched Joy’s mood darken, my inner feminist wanted to shout: Stop! Who cares what some guy thinks? Don’t let him tell you what to do! If you like the shoes, buy the shoes!
… but who was I to talk when just that morning, I’d ripped my Mary Poppins headband from my head and crammed it into my purse in shame?