Building a Western Businessman

Commercial real estate broker Rodger Chieffalo has his Western professional look down to a science.

“Adaptive reuse” is a development term that refers to renovating an old building to turn it into something new. That’s essentially what Rodger Chieffalo likes to do with hats – he takes an old hat (none of them are newer than 1970, he says) and adjusts the brim, ribbon and other features to give it a modern look. It’s a side project Chieffalo does alongside running his real estate company, Chieffalo Realty.

But the hat is just one part Chieffalo’s “Western professional” look. He has a method for putting together the rest of the ensemble, and he offered some tips on how to do it.

“A shirt that’s well-made has a tall collar. [If] all of the structure is well-made here, and the structure is well-made in the cuff, they’re not going to shrink up, they’re not going to distort, they’re always going to look nice. They’re always going to give a professional look, whether the man is wearing a tie or not.”

Sport Coat

The sport coat is the first thing that gets noticed on a man, Chieffalo says. Whether he wears a t-shirt or a dress shirt underneath, a good sport coat can turn any look into a professional one.
“That’s the key to a well-dressed man. I could be not wearing a sport coat, and I’d look like I was just hanging out. You judge for yourself. The sport coat really is the key to the whole deal.”

“Belt Bar”

Chieffalo uses the phrase “belt bar” to describe how he puts together his belt and buckle. Each day, he lays out his extensive collection of belts and buckles, piecing the two together.
“The belt matches the boots; the cuff links match the belt buckle. I try to keep the metals the same. I try to keep the leather colors the same.”

Cuff Links

Chieffalo has a unique collection of cuff links, made from items like old bullets or toy guns as a subtle nod to the Old West.
“The cuff links always follow the buckles. I’m going to wear silver cuff links because it’s a silver buckle. That’s the only guiding force.”


“Buy whatever is the most comfortable that you like. Jeans become invisible after you put all this other stuff together.”


“The key to footwear is finding a brand that is the most comfortable. Once you find a pair of shoes or boots that are comfortable, then I say only buy that brand.”