Undeniably, the Old Fashioned cocktail stands as a pillar of cocktail history, with its crisp blend of whiskey, bitters, and sugar on a block of ice. The iconic drink dates back to the early 19th century and has maintained its popularity thanks to its simplicity and perfect balance.

Born during a period of heavily sweetened and flavor-embellished cocktails, the "old-fashioned" style was reserved for lovers of a simpler time. Despite its vintage appeal, this hasn't deterred mixologists from inventing new alterations to the classic drink, using homemade syrups, unique bitters, or even fat-washed spirits, reflecting a modern taste for the old and new.

The quintessential Old Fashioned regularly features bourbon or rye whiskey, simple syrup, Angostura bitters, and topped with an orange twist. This is often what you’d receive if you ordered an Old Fashioned at a respected cocktail bar - a minimalist masterpiece of mixology.

Phil Ward of the New York City’s Death & Co. is famed for his Oaxaca Old Fashioned, making it one of the first modern cocktails that popularized the use of mezcal. This drink combines tequila, smoky mezcal, agave nectar, and bitters, therefore paying deep homage to Mexico's long-established tradition of agave cultivation.

Innovative approaches include the Fig Old Fashioned that swaps plain sugar for fig syrup, lending the drink a deeper, more mature dimension. Another tantalizing deviation is the Coffee Old Fashioned, coupling the hints of caramel and vanilla from whiskey with the bold, roasted tones of coffee liqueur.

The Monte Carlo cocktail performs a twist on the classic by replacing the conventional sugar cube with French herbal liqueur Bénédictine. It’s a captivating balance of strong rye whiskey with herbal sweetness, making an Old Fashioned that hovers between a Manhattan and a classic Old Fashioned.

If you saunter into a Wisconsin supper club and order an Old Fashioned, your bartender might just ask you for your preferred soda to top it off with. This version includes brandy, sugar, and bits of maraschino cherry and orange, added bitters, and finished off with soda.

Another modern twist is from seasoned bartender Ms. Franky Marshall, who crafts a bourbon-based concoction sweetened with coffee liqueur and a touch of vanilla syrup. She finishes it off with bitters and a twist of orange for a fragrant finish.

Don Lee at the bar PDT in New York City standouts with his Benton’s Old Fashioned. He infused bourbon with bacon fat before straining it, dashing it with maple syrup, and then adding aromatic bitters for a uniquely rich Old Fashioned.

Then there's the Si-Güey, a fresh tequila-based take on the Old Fashioned, created at Sasha Petraske’s renowned bar, Milk and Honey. It features lightly aged reposado tequila, dry curaçao, orange bitters, and finished with a splash of peated Islay Scotch, giving the cocktail a deliciously smoky twist.

Last but not least, there's the Caribbean-inspired Garvey Old Fashioned. It makes a surprising tropical twist to the Old Fashioned with its syrup made of pineapple juice and demerara sugar. Jamaican jerk bitters ramp up the drink's Caribbean influence, incorporating a burst of island spice to the classic cocktail.