How to Make a Classy Old Fashioned

by Kendon Shaw

This is a version of an old fashioned I make that's inspired by Longman & Eagle in Chicago. The idea here is that it's nicely balanced flavors enhance, not cover, your tasty bourbon.


  • 2 Ounces Bourbon
  • ½ Orange wedge
  • 1 Fresh cherry
  • ½ Teaspoons Simple syrup
  • Ice
  • 1 Big ice cube
  • 8 drops Bitters
  • Instructions

    Step 1

    Slice the orange. Just 1 half of a thin slice.

    Step 2

    Slice and pit the cherry. Fresh is better than maraschino.

    Step 3

    Throw the fruit in a shaker or a pint glass.

    Step 4

    Add a spoonful of simple syrup because it helps the medicine go down, the medicine go down. Less than a tsp. (You can make this by boiling 1 pt sugar to 1 pt water.)

    Step 5

    8 drops bitters. Exactly. Yes. Exactly.

    Step 6


    Step 7

    Throw some ice in there real nice.

    Step 8

    Pour two ounces of some delicious bourbon in the shaker.

    Step 9

    Stir politely. Don't shake it. It's not a polaroid.

    Step 10

    Put some fresh ice in your old fashioned glass and strain over the ice. I like to make these big cubes. They melt more slowly and look awesome.

    Step 11

    You could garnish with an orange peel or a cherry but I like it just like this.