The History Behind the Old Fashioned

The Old Fashioned isn't just a cocktail — it's the cocktail. Every other mixed drink is, in some sense, a variation on it. Understanding why means going back further than most people expect: not to a fancy private club in the 1880s, but to a barroom definition from 1806.

Where "cocktail" actually started

Long before anyone called a drink an Old Fashioned, American newspapers were already defining what a "cocktail" was. In 1806, a New York paper described it plainly: spirit, sugar, water, and bitters. That's the entire recipe. Tavern records from the 1790s show bartenders were already serving exactly this combination — they just didn't have a catchy name for it yet.

For decades, that four-ingredient formula was simply what a cocktail was. There was no need for a special name because there was no alternative to compare it to.

Then everything got fancier — so people asked for it "the old way"

By the mid-1800s, cocktail culture had taken off. Bartenders started adding liqueurs, absinthe, and elaborate garnishes to what used to be a simple drink. For some customers, that wasn't an improvement — it was clutter.

So they started asking bartenders for a whiskey cocktail made "the old-fashioned way": spirit, sugar, bitters, and little else. The phrase caught on. By 1880, Chicago newspapers were already writing about "old fashioned cocktails" as a known category, with rye whiskey the more common base at the time — bourbon came to dominate later. By the late 1880s, drink manuals were printing recipes under that exact name.

The Pendennis Club legend — and why historians don't buy it

Here's the twist most retellings leave out. The most famous origin story credits the Pendennis Club, a private club in Louisville, Kentucky, claiming a bartender there invented the drink around 1880 for a bourbon distiller named Colonel James E. Pepper, who later introduced it to New York's Waldorf-Astoria.

It's a great story. It's also almost certainly not true — at least not as an origin story. Cocktail historians point out that "old fashioned cocktails" were already being written about in Chicago before the Pendennis Club even opened its doors in 1881. The earliest print source for the legend doesn't show up until 1931, more than 50 years after the drink's name was already in circulation. Even a 1913 cocktail book written by the club's own longtime manager doesn't mention an Old Fashioned recipe at all, let alone credit it to the club.

What the Pendennis Club likely did do is help refine and popularize a particular version of a drink that already existed — muddled sugar, Angostura bitters, a slice of orange, a cherry. That combination, however it came together, is close to how a lot of people still picture an Old Fashioned today.

How the recipe kept shifting

The Old Fashioned didn't stay static. Fruit garnishes — orange slices, cherries — weren't part of the earliest versions; they crept in around 1930. During Prohibition, when bootleg liquor tasted rough, bartenders leaned harder on sugar and muddled fruit to cover it up, pushing the drink toward something sweeter and more elaborate than the original.

Decades later, the craft cocktail revival pushed things back the other way. Bars in the 2000s started treating the Old Fashioned less as a fixed recipe and more as a template — swap the whiskey, change the bitters, adjust the sweetener, and you get a related but distinct drink. The Sazerac, the Toronto, even tequila-based versions all trace back to the same four-part structure: spirit, sweetener, bitters, minimal dilution.

Why it still holds up

What makes the Old Fashioned endure isn't nostalgia. It's that the format respects the spirit instead of covering it up. A good bourbon or rye doesn't need much — a little sugar to round the edges, a dash of bitters for depth, maybe a twist of orange for aroma. Everything else is optional.

That's the same idea behind our Old Fashioned Club Sweatshirt — no gimmicks, no over-design, just something built to last for people who'd rather get it right than get it flashy. Whether you're the one making the drink or the one waiting for it, there's a quiet confidence in ordering — or wearing — an Old Fashioned.