The Old Fashioned is the cocktail equivalent of a white t-shirt. Get it right and nothing else matters. Get it wrong—too sweet, wrong whiskey, muddled fruit salad—and it's unwearable.
I've been making Old Fashioneds for fifteen years and tending bar for a portion of that, and the best thing I've learned is this: master the original before you riff on it. Every variation below starts from the same foundation. Skip the foundation and the riffs fall apart.
The Classic Old Fashioned (Get This Right First)
You need:
- 2 oz bourbon or rye (100 proof preferred)
- 1 barspoon (about 1 tsp) rich demerara syrup (2:1 sugar to water)
- 2-3 dashes Angostura bitters
- Orange peel, expressed
- One large ice cube or sphere
Method: Combine syrup and bitters in a rocks glass. Add bourbon. Add ice. Stir gently for 15-20 seconds—you're chilling and diluting, not blending a smoothie. Express the orange peel over the surface (squeeze it skin-side down so the oils spray across the drink) and drop it in.
That's it. No muddled cherries. No muddled oranges. No soda water. The original recipe from the 1880s didn't include any of that, and neither should yours.
The bourbon pick: Wild Turkey 101 ($25) is the bar industry standard for a reason—the 101 proof holds up to dilution, the high-rye mashbill provides spice structure, and the price means you can make these all night. Evan Williams Bottled-in-Bond ($18) is the budget play that makes bartenders nod.
Variation 1: The Maple Old Fashioned
Swap: Replace demerara syrup with Grade A dark maple syrup (1 barspoon)
Add: 1 dash black walnut bitters alongside the Angostura
Bourbon: Maker's Mark 46 ($40) — the wheat and vanilla amplify the maple
This is the variation that converts people who think they don't like whiskey cocktails. Real maple syrup (not pancake syrup, please) adds an earthy, autumnal sweetness that plays off bourbon's existing vanilla and caramel notes. The key is restraint—one barspoon, not a pour. You want a whisper of maple, not a stack of pancakes.
Dark amber or Grade A dark maple syrup works best. The lighter grades are too subtle to register against bourbon. And skip the maple-flavored bourbons—you're getting the real thing from the syrup; you don't need artificial maple in the whiskey too.
Variation 2: The Smoked Old Fashioned
Add: Smoke the glass with a smoking cloche and hickory or cherry wood chips
Bitters: Replace Angostura with 2 dashes Bittermens Hellfire Habanero Shrub (or keep Angostura if you don't want heat)
Bourbon: Old Forester 1920 ($55) — the 115 proof and dark fruit stand up to smoke
This is the Instagram darling of Old Fashioned variations, and I'll admit I was skeptical. Turns out, when done correctly, smoke adds genuine complexity—not just theater. The trick is 15 seconds of smoke under the cloche, not 60. You want campfire, not house fire.
If you don't have a smoking cloche (the Breville is $50 and worth it), a kitchen torch and a cedar plank work in a pinch. Toast the plank, invert the glass over the smoke for 10 seconds, then build the drink. Don't use liquid smoke. Ever. That stuff belongs on ribs, not in a glass.
Variation 3: The Mezcal Old Fashioned
Base: 1.5 oz reposado mezcal + 0.5 oz bourbon
Syrup: Agave nectar (1 barspoon)
Bitters: 2 dashes mole bitters (Bittermens Xocolatl works perfectly)
Garnish: Grapefruit peel instead of orange
Mezcal: Del Maguey Vida ($30) — clean smoke, good backbone
Bourbon: Buffalo Trace ($28) — gentle enough to let the mezcal lead
This one's a curveball, and it's my current obsession. Mezcal's natural smoke replaces the oak char of bourbon as the dominant flavor, while the half-ounce of bourbon adds sweetness and body that straight mezcal lacks. The agave nectar ties the mezcal to its origins, and the mole bitters add cocoa and spice depth that makes the whole thing feel like it was always meant to exist.
The grapefruit peel is non-negotiable. Orange is too sweet here—grapefruit's bitterness provides the counterpoint this drink needs. Express it aggressively. You want those oils.
Variation 4: The Rye Old Fashioned
Base: 2 oz straight rye whiskey
Syrup: Rich demerara (same as classic)
Bitters: 2 dashes Angostura + 1 dash orange bitters
Garnish: Lemon peel instead of orange
Rye: Rittenhouse Rye BiB ($28) or Wild Turkey 101 Rye ($25)
Purists will point out that the original Old Fashioned was probably made with rye, not bourbon. They're right. Pre-Prohibition cocktails defaulted to rye whiskey, and there's a reason: the dry spice and herbal character of rye creates a cocktail with more backbone and less sweetness than its bourbon counterpart.
The lemon peel swap matters. Rye's spice character harmonizes with lemon's bright acidity in a way that orange doesn't quite achieve. The orange bitters add a layer of citrus depth without the sweetness of an orange peel. This is the Old Fashioned for people who find the bourbon version too dessert-forward.
Rittenhouse at 100 proof and $28 is the quintessential cocktail rye—enough intensity to hold up, enough complexity to reward sipping between stirs.
Variation 5: The Black Walnut Old Fashioned
Swap: Replace Angostura with 3 dashes Fee Brothers Black Walnut Bitters
Syrup: Brown sugar simple syrup (2:1 brown sugar to water)
Bourbon: Knob Creek 9 Year ($36) — the oak and nut notes align perfectly
This is the sleeper hit of the list. Black walnut bitters are one of those ingredients that seem gimmicky until you taste them in context. They add a toasted, nutty depth that amplifies bourbon's existing oak character—it's like turning the bass up on a speaker. You didn't know it was missing until it's there.
Brown sugar syrup instead of demerara adds a hint of molasses that connects the walnut bitters to the bourbon's caramel notes. Three dashes instead of two because walnut bitters are subtler than Angostura. And Knob Creek 9 Year at 100 proof has enough oak tannin and nutty character to meet the bitters halfway.
Variation 6: The Cherry-Forward Old Fashioned
Add: 1 barspoon Luxardo maraschino cherry syrup (from the jar)
Muddle: One Luxardo cherry in the glass before building
Bitters: 2 dashes Angostura + 1 dash cherry bitters
Bourbon: Four Roses Small Batch ($34) — the ripe fruit notes amplify the cherry
I know I said no muddled fruit. Here's the exception. A single Luxardo cherry (not a neon-red maraschino; those are an abomination) muddled gently at the bottom of the glass adds genuine cherry flavor without turning the drink into a fruit cocktail. The cherry syrup from the jar adds sweetness that replaces some of the demerara—use half the usual demerara amount.
Four Roses Small Batch is the ideal base because its OBSK and OBSO recipes already carry ripe berry and stone fruit notes. The cherry in the drink doesn't add an alien flavor—it amplifies what's already there. This is the Old Fashioned that people who "don't like whiskey" end up ordering twice.
Variation 7: The Winter Spice Old Fashioned
Syrup: Spiced demerara syrup (simmer 2:1 demerara with 2 cinnamon sticks, 4 cloves, and 3 allspice berries for 10 minutes, strain)
Bitters: 2 dashes Angostura + 1 dash Bitter Truth Jerry Thomas Bitters
Garnish: Orange peel + cinnamon stick
Bourbon: Woodford Reserve ($35) — the vanilla and baking spice are holiday-ready
This is the December Old Fashioned. The spiced syrup does the heavy lifting—cinnamon, clove, and allspice in demerara create a warm, holiday-adjacent sweetness that transforms Woodford Reserve's existing baking spice notes into something that smells like a holiday you actually want to attend.
Make the syrup in a batch—it keeps for 2-3 weeks in the fridge. The Jerry Thomas bitters add a layer of dark spice that Angostura alone can't achieve. And the cinnamon stick garnish isn't decorative—stir the drink with it once before sipping. It adds just a touch more cinnamon aroma with each sip.
Fair warning: make this for guests in December and you'll be making it every December for the rest of your life. I speak from experience.
Technique Notes That Actually Matter
Stirring time: 15-20 seconds with a large ice cube. You want roughly 0.5 oz of dilution. Under-stirred and the drink is hot and concentrated. Over-stirred and it's watered down. Time it until you develop a feel for it.
Ice: One large cube or sphere. Crushed ice is for juleps. Small cubes melt too fast and over-dilute. If you don't have a large ice mold ($12 on Amazon, buy one), use the biggest cubes your tray makes.
Glass: A proper rocks glass, 8-10 oz capacity. Not a tumbler. Not a wine glass. Not a mason jar. The wide rim lets you nose the drink while you sip—half the experience is aromatic.
Expression: When expressing a citrus peel, hold it 6 inches above the drink, skin-side down, and squeeze firmly. You should see a fine mist of oils spray across the surface. Then run the peel around the rim and drop it in. This step adds more flavor than most people realize.
The Old Fashioned endures because it trusts the whiskey. Every variation above respects that principle—the additions enhance the spirit, they don't hide it. If your Old Fashioned doesn't taste like whiskey, you've made a different drink. Start over.
