Some claim the first use of the specific name "Old Fashioned" was for a Bourbon whiskey cocktail in the 1880s, at the Pendennis Club, a gentlemen’s club in Louisville, Kentucky. The recipe is said to have been invented by a bartender at that club, and popularized by a club member and bourbon distiller, Colonel James E. Pepper, who brought it to the Waldorf-Astoria Hotel bar in New York City. Others point out that the term was already in use before the Pendennis Club was founded.
An 1895 recipe specifies the following:
Mix with small bar spoon and serve, leaving spoon in glass.
Most modern recipes top off an Old Fashioned cocktail with soda water. Purists decry this practice, and insist that soda water is never permitted in a true Old Fashioned cocktail. Many respected sources (e.g. Maker's Mark) list an Old Fashioned as containing soda water, forgoing the bitters altogether.
Many bartenders add fruit, typically an orange slice, and muddle it with the sugar before adding the whiskey. This practice likely began during the Prohibition as a means of covering the bitter taste. Another explanation for the practice is that citrus is often used in place of bitters in areas where citrus fruit grows (such as Florida and California). Hence, the fresh San Diego old fashioned () uses limes, lemons, oranges, and soda water rather than bitters and simple syrup. The drink may have been imported to California during WWII, when many Midwestern and Southern boys moved to San Diego for the Navy.
Purists advocate using just enough plain water (called "branch" water) to fully dissolve the sugar without diluting the whiskey, although many whiskey drinkers advocate diluting it by at least 50% to prevent the taste buds from becoming paralyzed by the high alcohol content.
Bartenders often use a dissolved sugar-water premix called simple syrup, which is faster to use and eliminates the risk of leaving undissolved sugar in the drink, which can spoil a drinker's final sip. Others use only the juice of a maraschino cherry, along with the muddled and mangled cherry left at the bottom of the glass.
One popular garnish is a maraschino cherry fastened to the back of an orange wedge using a toothpick. Others prefer to use orange zest with the maraschino cherry.
See also List of cocktails.