It began 36 years ago as a small menswear shop on the city's South Side.
But its future lay in the west.
Today, the family-owned and operated Alcala's Western Wear is a 12,000-square-foot cowboy superstore, where boots come in 10,000 varieties and the belt buckles are made by hand.
The business, a family-owned enterprise run by seven of the 11 children of founders Luis and Carmen Alcala, went west before it went western - moving to the city's west side in 1982, looking for new markets and cheaper rent.
Luis Alcala, who left Mexico looking for work and picked cotton in Mississippi before settling in Chicago in 1951, began the store in 1972 from inventory he'd amassed while working for years at the city's Maxwell Street Market.
A few years later, at the suggestion of one of their sons - the couple brought in a small collection of western wear. And watched in surprise as the items flew off the shelves.
The caballero look, thanks in part to the city's large Hispanic population, was a hit.
It wasn't long before the chaps, hats and boots had taken over the small storefront and Luis Alcala made the decision to buy the adjacent building, knock down the wall and expand.
As they celebrate the store's 36th anniversary this month, the 20 Alcala family members involved in the business oversee a dramatically different enterprise than the one begun in 1972 by Luis and Carmen, now retired in Mexico.
Today, the shop, at 1733 W. Chicago Ave. in the city's East Village neighborhood, also caters to women and children. A second expansion has brought the store to over 12,000 square-feet and four store fronts. Their customers travel from all over world and shop the store's website.
"The whole family shops here. There is something for everyone," says Robert Alcala, Louis and Carmen Alcala's son and the store's general manager.
The brands include Scully's, the popular western wear shirt made in Denver, Lucchese Boots, custom designed for Alcala's in El Paso, Tex., and a wide array of accouterments including spurs, belts, buckles and more.The store also offer complimentary on-site tailoring, hat shaping and cobbler services.
"I go for special, hard to find items," says Sanchez. "I go for very normal items. I always go back because they were so helpful the last time," says Sanchez.
Sanchez says he shops for boots, ornate, hand-made belt buckles and clothes for his little boy.
Alcala's also has elements of a western wear museum, with exhibits displaying boots made for Andre the Giant and Elvis Presley.
There is also a 7 1/2 foot rattlesnake skin and a 25-foot Anaconda python skin given to
Alcala's by the Lucchese Boot Company.
The back wall of the shop touts the various accolades Alcala's has received over the years, including two Playboy covers featuring Alcala's custom-made boots.
A giant bison head decorates the exit.
Alcala says the store draws its customers from every ethnic and social background. From $20 straw hats to $5,000 Stetsons, some decorated with rhinestones, some diamond-studded, the store sells 4,000 to 5,000 hats a year.
Some customers, Alcala says, come simply out of nostalgia.
"Everyone wants a piece of old Americana," he says.