Fleming’s Old Fashioned Recipe: Bourbon-Infused Classic With a Twist

This timeless cocktail embodies the essence of classic mixology with a refined approach. The key lies in balancing the bold bourbon with just the right amount of sweetness and bitterness.

What sets this version apart is the meticulous technique—muddling the sugar with bitters and citrus creates a foundation that elevates the bourbon to its full potential. The result is a smooth, well-rounded drink that honors tradition.

Ingredients for Fleming’s Old Fashioned

Eight ingredients craft this refined bourbon cocktail with classic sophistication and depth.

The bourbon is non-negotiable here. Woodford Reserve or Buffalo Trace deliver that caramel-rich backbone this drink demands. For sugar, Demerara adds a molasses complexity that white sugar lacks—Whole Foods and Williams Sonoma stock it. Angostura bitters are the gold standard; don’t settle for artificial substitutes. The orange should be fresh (navel works well) for both muddling and garnish.

No Demerara? Turbinado sugar works in a pinch. Out of Luxardo cherries? Brandied cherries are an acceptable second choice, but avoid the neon maraschino kind. For bitters, Reagan’s Orange Bitters can complement the Angostura. If you’re feeling adventurous, a barspoon of maple syrup can replace the sugar—just use half the amount.

This cocktail is best served immediately after stirring. Prep your garnishes in advance—cherries and orange slices keep 3-4 days in the fridge. Bourbon and bitters stay good indefinitely if stored properly in a cool, dark place.

Step-by-Step Instructions for Fleming’s Old Fashioned

Master the technique behind this timeless cocktail with precision and classic refinement.

Step 1: Muddle the Sugar with Bitters and Citrus

Place the 1 tsp Demerara Sugar in an old fashioned glass. Add the 3 dash Angostura Bitters directly on top. I use a muddler to gently press the orange slice into the sugar and bitters, releasing its oils without pulverizing the fruit.

The goal is to dissolve the sugar while infusing the bitters with citrus essence. You should see the sugar crystals break down into a wet, aromatic paste at the bottom of the glass. This foundation layer is critical for balanced flavor distribution throughout the drink.

Step 2: Build the Cocktail Base with Bourbon

Add the 4 oz Bourbon Whiskey to the glass containing the muddled mixture. I always use a high-proof bourbon here—it stands up better to the sugar and bitters while maintaining the cocktail’s bold character.

Stir vigorously with a bar spoon for 15-20 seconds to fully incorporate the dissolved sugar and bitters into the bourbon. Watch for the mixture to take on a slightly cloudy appearance as the sugar fully integrates. The liquid should coat the spoon evenly when properly combined.

Step 3: Add Ice and Incorporate the Luxardo Cherry

Fill the glass with the 4 pieces Ice Cubes—I prefer large, dense cubes that melt slowly. This prevents over-dilution while keeping the drink properly chilled. Add the 1 whole Luxardo Cherries to the glass, allowing it to sink naturally among the ice.

The cherry will begin to infuse the cocktail with its rich, slightly sweet flavor as it sits. Gently stir the mixture for another 10 seconds to distribute the cold temperature evenly without breaking up the ice too much. The drink should take on a beautiful amber hue at this stage.

Step 4: Finish with Club Soda and Orange Peel

Add the 1 tsp Club Soda to the glass. This subtle effervescence brightens the cocktail without overwhelming its classic profile. Give it one final gentle stir to incorporate the soda throughout.

Now express the 1 piece Orange Peel over the drink by holding it skin-side down above the glass and giving it a firm twist. This releases the citrus oils onto the surface, creating an aromatic finish. Rub the peel along the rim of the glass before dropping it in as garnish. The cocktail is now ready to serve, exhibiting perfect balance between sweet, bitter, and citrus notes.

Perfect Pairings for This Dish

Food Pairings

This cocktail pairs beautifully with rich, savory dishes. I love serving it with a charcuterie board featuring aged cheddar, prosciutto, and marinated olives. The bourbon’s caramel notes complement the saltiness perfectly. 🍽️

Steakhouse Classics

A perfectly cooked ribeye steak with a side of creamy mashed potatoes makes an ideal match. The drink’s bitterness cuts through the fat, while the citrus brightens each bite. Fleming’s serves this exact pairing in their restaurants.

Cheese Selections

For a lighter option, try aged Gouda or blue cheese. The sweetness of the Demerara sugar in the cocktail balances the sharpness of these cheeses. I always include candied pecans for textural contrast.

Dessert Complements

Dark chocolate desserts work remarkably well. A 70% cacao chocolate truffle or flourless chocolate cake lets the bourbon’s vanilla notes shine. The bittersweet profile creates a harmonious finish to any meal.

Cigar Pairing

For a true Fleming’s experience, pair with a medium-bodied cigar. I recommend a Macanudo Café – its nutty, creamy profile complements the cocktail without overpowering it. 💛

Frequently Asked Questions