The worst Old Fashioned I ever had was at a craft cocktail bar in Brooklyn that charged $18 for it. The bartender muddled the orange and cherry into a pulpy sludge, drowned it in simple syrup, and served it over crushed ice that melted before I finished half the drink. The best one cost $9 at a dive bar in Louisville, made by a seventy-something bartender who'd been making them since before I was born. Sugar cube. Three dashes of bitters. Two ounces of Wild Turkey 101. One large ice cube. Orange peel expressed and dropped. Done in ninety seconds, perfect in every way.
The lesson: the Old Fashioned doesn't care about your Instagram-worthy smoke show or your dehydrated citrus garnish. It cares about proportion, quality bourbon, and not overthinking things that should be simple.
This is the cocktail that invented the category — quite literally. When drinkers in the 1880s got tired of bartenders adding weird liqueurs and absinthe to their whiskey, they started asking for it made "the old-fashioned way." Just spirit, sugar, bitters, water. The name stuck. The formula endured. And now, 140 years later, it's the drink that separates people who understand bourbon from people who just order bourbon.
The Recipe
Ingredients:
- 2 oz bourbon (see our picks below)
- 1 sugar cube (or ¼ oz simple syrup, or ¼ oz demerara syrup)
- 3 dashes Angostura bitters
- Orange peel
- 1 large ice cube (or 3-4 regular cubes)
- Luxardo cherry (optional, but if you're using bright red maraschino, don't)
Equipment:
- Old Fashioned glass (rocks glass)
- Bar spoon
- Muddler (if using sugar cube)
- Peeler or paring knife
Instructions:
- Build in the glass. Place the sugar cube in your Old Fashioned glass. Add the bitters directly onto the cube. Add a bar spoon of water (about ¼ oz). Muddle gently until the sugar dissolves — you're not making caipirinha, just breaking down the cube. This takes 15-20 seconds.
- Add bourbon. Pour your 2 oz over the sugar-bitters mixture. No ice yet.
- Stir with ice. Add your large ice cube. Stir with a bar spoon for 20-30 seconds — you want dilution and chill. The drink should feel noticeably colder in your hand. If using regular cubes, stir for 15-20 seconds (they dilute faster).
- Express the orange peel. Cut a 2-inch strip of orange peel, avoiding the white pith. Hold it over the drink, colored side down. Fold it sharply to express the oils — you should see a small spray of citrus oil hit the surface. Rub the peel around the rim of the glass, then either drop it in or discard (your choice).
- Garnish. If using a Luxardo cherry, add it now. If not using a cherry, don't — it's not required.
The Quick Version: Sugar cube, bitters, splash of water — muddle. Add bourbon, add big ice cube, stir 25 seconds. Express orange peel over drink, drop it in. That's it.
The Details That Matter
The Sugar Question: Traditional is a sugar cube with Angostura-soaked muddling. It gives you texture, ritual, and tiny undissolved sugar crystals that create pockets of sweetness. But here's the truth — demerara simple syrup (1:1 demerara sugar to water) gives you better flavor. The molasses notes complement bourbon's caramel and vanilla instead of just adding generic sweetness. Regular simple syrup works fine but tastes flat in comparison. If you're making more than one, skip the cube and use syrup. If you're making one for yourself on a Tuesday night, the cube feels right.
The Ice Question: One large cube is ideal — it chills and dilutes slowly, keeping your drink cold for 20-30 minutes without watering it down. Regular cubes work, but you'll need to drink faster or accept a weaker cocktail by the end. Crushed ice is wrong. Full stop. This isn't a tiki drink.
The Stirring Technique: Hold the bar spoon between your middle and ring finger. Place the back of the spoon against the inside of the glass. Rotate the glass with your other hand while keeping the spoon stationary — this creates a smooth circular motion. Or just stir in circles like a normal person. Both work. The goal is 20-30 seconds of contact between ice and liquid. You'll feel the glass get cold. That's your signal.
The Orange Peel Question: Expressing the peel over the drink releases citrus oils that add aroma and a tiny amount of flavor. It's not optional — it transforms the drink. Dropping the peel in gives you ongoing aromatics as you drink. Discarding it after expressing gives you a cleaner aesthetic. I drop it in because I paid for the orange. The "express vs drop" debate is 90% bartender ego, 10% actual preference.
The Cherry Debate: Luxardo cherries are the only cherries worth using — dark, boozy, complex. They cost $20 for a jar but last six months. Bright red maraschino cherries taste like childhood and ruin the drink. No cherry at all is perfectly respectable. This is a bourbon cocktail, not a sundae.
Our Bourbon Picks
Best Overall: Wild Turkey 101 ($28-32)
This is the platonic ideal of an Old Fashioned bourbon. The 101 proof gives you enough backbone to stand up to dilution and ice. The flavor profile — vanilla, baking spice, caramel, a touch of cinnamon — is exactly what the cocktail wants. It's not so expensive that you feel guilty using 2 oz, and it's not so subtle that it disappears behind the sugar and bitters. I've made hundreds of Old Fashioneds with dozens of bourbons, and I keep coming back to this. Read our full review.
Best Value: Elijah Craig Small Batch ($26-30)
For under $30, this brings surprising complexity — brown sugar, nutmeg, dried fruit. The 94 proof is slightly lower than Wild Turkey, so you get a softer cocktail. If you're making Old Fashioneds for guests who don't drink bourbon neat, this is the move. Approachable, balanced, never harsh. Full review here.
Best Splurge: Buffalo Trace ($32-45, depending on your market)
Technically not a splurge bottle, but it drinks like one in an Old Fashioned. The honeyed sweetness and gentle oak play beautifully with demerara syrup. The 90 proof means you need to stir a bit less to avoid over-dilution. This is the bourbon for when you're making one perfect Old Fashioned for yourself on a Friday night. See our tasting notes.
Best High-Proof Option: Old Forester 100 ($24-28)
If you like your Old Fashioneds assertive, the 100 proof delivers. Banana, cherry, and baking spice that cut through the sugar without getting aggressive. It's a bartender favorite for a reason — works in cocktails, costs less than premium bottles, available everywhere. For a broader comparison of options, check out our best bourbons roundup.
Find these bottles and more at CWSpirits — use code BOOZEMAKERS5 for 5% off your order.
What Our Panel Says
Marcus Chen, The Explorer: "I learned to make Old Fashioneds during lockdown using whatever I had — Maker's Mark and regular sugar cubes from the grocery store. Honestly? Still delicious. Now I keep a bottle of Elijah Craig specifically for them because it's $28 and makes me look like I know what I'm doing when friends come over. The trick I finally figured out: stir way longer than feels natural. Like, a full 30 seconds. Game changer."
William Hayes, The Connoisseur: "The first proper Old Fashioned I had was at the Seelbach Hotel in Louisville in 1994. The bartender used Woodford Reserve, a single large sphere of ice, and a technique I've tried to replicate ever since — he expressed the orange peel, then flamed it briefly with a match before dropping it in. The aroma was extraordinary. I've been making them at home every Sunday evening for thirty years now, always with a sugar cube, always with bourbon between 100-110 proof. It's ritual."
Sophia Laurent, The Host: "I batch Old Fashioneds for dinner parties — pre-mix the bourbon, demerara syrup, and bitters in a pitcher, then just pour over ice and garnish when guests arrive. Did this for twelve people last month using Buffalo Trace, and three different friends asked for the recipe. Served them alongside bacon-wrapped dates and aged cheddar. The key to batch service: make them slightly less sweet than you would solo, since people's palates vary. I also set out Luxardo cherries and let guests choose."
Variations Worth Trying
Smoked Old Fashioned: Use a smoking gun or torch to smoke the glass with applewood or cherrywood before building the drink. Or float a few drops of mezcal on top (⅛ oz). The smoke amplifies bourbon's char and oak notes. This looks impressive and actually tastes different — deeper, more campfire, more winter evening.
Maple Old Fashioned: Swap the sugar for real maple syrup (¼ oz, grade A dark). This is fall in a glass — maple and bourbon have natural affinity. Add a dash of Angostura and a dash of orange bitters. Express an orange peel. It's sweeter than the classic, so use a higher-proof bourbon (100+) to balance.
Oaxacan Old Fashioned: Replace half the bourbon with mezcal (1 oz bourbon, 1 oz mezcal). The smoke and agave create something entirely different while keeping the Old Fashioned structure. Use agave syrup instead of sugar. This is technically a different cocktail, but the format is identical. If you like mezcal, this is addictive.
Rye Old Fashioned: Swap bourbon for rye whiskey. You get more spice, less sweetness, a drier finish. Use the same recipe but consider upping the sugar slightly (⅓ oz simple syrup) to balance rye's peppery bite. This is a New York drink — sharper, less forgiving, excellent.
Common Mistakes
Muddling the orange and cherry: This is the number one crime against the Old Fashioned. Muddling fruit creates bitter oils from the pith and turns your cocktail into chunky juice. The orange peel is for expressing oils, not pulverizing into mash. If a bartender muddles your orange, send it back.
Using too much sugar: The sugar is there to soften bourbon's edges and add body, not to make a sweet cocktail. If you can't taste the bourbon clearly, you've overdone it. Start with ¼ oz (one cube or syrup measure) and adjust from there. Most people prefer slightly less sweet than more.
Not stirring long enough: Dilution is not the enemy — it's essential. An unstirred Old Fashioned is too strong, too hot, and unbalanced. You need 20-30 seconds of stirring to integrate the ingredients and bring the proof down to a drinkable level. The cocktail should be cold and smooth, not room-temperature and aggressive.
Using low-proof bourbon: Anything under 90 proof gets lost in this drink. The ice dilutes it, the sugar softens it, and you end up with something watery and forgettable. Aim for 94-110 proof. The cocktail was designed for high-proof spirits — it's in the DNA.
Final Note
The Old Fashioned doesn't need improvement. It needs respect. Use good bourbon. Don't oversweeten. Stir properly. Express that orange peel. The cocktail will reward you with exactly what it's been delivering since the 1880s — proof that the simplest things, done right, are often the best things.
Make one tonight. Make it well. Then make another.
