Raised in the Bronx, Ralph Lifshitz—the son of Russian Jewish immigrants—spent his teen years absorbing the charm and charisma of Fred Astaire and Cary Grant, attempting to imitate their sense of style. Fifty years and one name change later, Ralph has more than fulfilled his high school fantasy…as the fashion designer who kicked off his career with a line of neckties for Bloomingdale’s under the brand Polo by Ralph Lauren.

Ralph Lauren is the godfather of country-club cool and has marketed his cable-knit sweaters and corduroys not as products but as a lifestyle. Through the years, he has developed an impeccably polished persona that he then sells to his WASP-y clientele. Here in Chicago, we get to experience Ralph Lauren’s Nantucket world beyond the typical navy blazers and ad campaigns. Michigan Avenue boasts the biggest Ralph Lauren store in the world and the only RL restaurant.

Walking through the entrance, you immediately feel like you are at “the club.” If you have to wait for a table, you can lounge around in a chair near the black marble fireplace and watch women coat-check their furs. As if the people-watching isn’t enough, the walls are crowded with paintings and prints—ranging from portraits of the well groomed to black-and-white photos of Marilyn Monroe. The swanky dining room is dimly lit, filled with leather chairs and classic white tablecloths. The place is decked out in mahogany and brass to complete that old-money feel.

Although some of the menu items are more sophisticated (like a baked Camembert appetizer topped with maple syrup and poached pears), the menu’s appeal rests on its classic Americana dishes. The main courses for dinner are heavy on the meats, but there are also simpler selections. I was taken by the all-American hamburger, of all things. Although I’m not usually a burger person, Ralph’s version—sirloin on a challah bun—is delectable. Despite the somewhat intimidating atmosphere of the restaurant, there is nothing daunting about this burger but its size. When topped with white cheddar cheese, bacon, and mushrooms, it’s hard to leave any behind.

This creates a dilemma, though, because saving room for dessert is a must. All the classics are here: New York cheesecake, Key lime pie, or a banana split. If you want something with a little more pizzazz, however, the restaurant serves tableside preparations of bananas Foster and strawberries Romanoff (made by soaking strawberries in orange juice and liquor before quickly sautéing them and topping them with whipped cream). Among the house favorites is a selection of Bunky’s cookies, named for one of the top-selling associates in the Ralph Lauren men’s department who lunches at RL with lady friends every afternoon.

My friend commented that the diners at RL, dressed in pearls and khakis, seemed specifically cast to sit in this Chicago window into Ralph’s world. There is no reason to feel out of place in your jeans, though. Mr. Lauren is only playing a role, and there is no reason why you can’t, too.