Brian Chilson

I went to Jon Stone of the Independent with a simple question. How do I learn the basic rules of not looking stupid?

He paused. He smiled. “Well, you don’t look stupid,” he said. I didn’t believe him and still don’t, but it was an awfully nice thing to say.

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Stone, along with his business partners, has run the menswear retailer for three years now, with one outlet in Little Rock and two in Northwest Arkansas. Knowing nothing about fashion aside from a vague list of prohibitions I’ve accumulated over the years — for some reason, you can’t wear socks with sandals? — I’d asked Stone if he’d be willing to dress me to the best of his abilities. And here we were one sweltering July afternoon, him efficiently tape-measuring my dimensions while I lobbed out the sort of why-is-the-sky-blue questions a toddler asks his dad.

“OK. So what’s that rule with buttoning jackets?” I asked.

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“If it’s a soft, three-button jacket, it’s the middle button. If it’s a two-button jacket, it’s the top button,” he said.

“Never the bottom button?”

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“Never the bottom button,” he said. “Never.”

“Then why is it there?” I demanded.

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“Um — decorative issues?” he replied, diplomatically, patiently.

In the dressing room, he held out a jacket he’d selected for me, and I began to shrug it on. No, Stone chided, not one arm at a time, put it on like this.

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“Both arms at once?” I asked. “But why?”

“That’s just how we rock ‘n’ roll, man, in the sartorial world.”

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He fitted me with pants and shoes and loaned me his belt for the photo shoot. He nodded. “Yes, this will show off your little petite figure very well,” he said. Our photographer suppressed a snicker. I glared at him.

Afterward, dressed again in my everyday, shapeless, thrift store officewear, I asked Stone if he had a short list of definite things not to do when it comes to dress.

“It’s very individual,” he said. “For you, I wouldn’t wear blousy, pleated pants that have a huge, wide bottom on the bottom, because it’s going to add years to you and add a lot of weight.”

“Shirts” — he glanced at my Dilbert-esque short sleeve button up, straight from Goodwill — “I always prefer a long-sleeve shirt with the sleeves rolled up.”

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“The rule of thumb is this: Less is best. The more simple and basic the better … . A peaked lapel double-breasted jacket for you would be just too much.” I nodded, though I had to look up what a peaked lapel is when I got back to the office, and I’m still confused about what makes anything double-breasted.

“And get a good haircut. Where do you get your hair cut?”

Wherever costs less than $20, I told him, which is true. The last time, I think, was several months ago at a place called Sports Clips, which happened to be next to the pet store in a strip mall. I was buying dog food. I needed a haircut. I got a haircut. Jon, I said, you’ve got to understand: I’ve made huge gains. Until two years ago or so, I cut my hair myself or had a friend do it. Buying pants outside of a thrift store was unheard of. I buy a $20 pair of Target khakis and I feel like I’ve accomplished something amazing.

“Well,” he said. “Thank God you’ve met me.”

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