Bourbon Old Fashioned

A bourbon Old Fashioned is one of those cocktails that never goes out of style—and in our house, it’s one of my husband’s favorites. He’s not a huge drinker day to day, but when he does pour an occasional after-dinner cocktail, it’s often a carefully crafted Old Fashioned. It’s simple, elegant, and lets the bourbon shine with its deep, rich character softened by just a touch of sweetness.

This classic cocktail has roots that stretch back to 1881, when it’s said a bartender at The Pendennis Club—a gentlemen’s club in Louisville, Kentucky—created the drink in honor of Colonel James E. Pepper, a well-known bourbon distiller. Pepper would later bring his beloved bourbon and this cocktail to the famed Waldorf Astoria in New York City. More than a century later, the Old Fashioned remains a staple in cocktail culture, especially on a cool evening, and something warm and smooth feels just right.

My husband didn’t always drink bourbon. He came to it a little later in life, sometime before we had kids. I remember those Brooklyn evenings when he’d mix himself an Old Fashioned, unwinding with that amber-hued drink in hand. Over the years, what started as curiosity grew into appreciation, and now we have a rather extensive bourbon collection—each bottle with its own story and flavor profile.

Louisville and the Legacy

In 2015, Louisville made it official: the Old Fashioned was declared the city’s signature cocktail. Every June, the city hosts “Old Fashioned Fortnight,” a two-week celebration filled with bourbon tastings, cocktail specials, and events that culminate in National Bourbon Day on June 14. I can’t think of another cocktail with quite as much ceremony or civic pride behind it. But the Old Fashioned earns its fanfare—it’s a drink that’s equal parts sophistication and nostalgia.

Pop culture certainly helped revive its popularity. Like many, both my husband and I were devoted fans of Mad Men, and I’d be lying if I said Don Draper’s signature drink didn’t catch my attention. The show’s moody aesthetic and mid-century charm helped reintroduce the Old Fashioned to a whole new generation. According to The Washington Post, the rise in bourbon production and demand during the show’s run from 2007 to 2015 mirrored the habits of its stylish, hard-drinking characters.

Though bourbon isn’t my go-to spirit of choice, I can’t deny the allure of a well-made Old Fashioned. There’s something about its smoothness that sneaks up on you—it’s both bold and gentle, a drink that’s stood the test of time with good reason.