Sadly, the transition into fall is upon us and we must start to say goodbye to summer. Thankfully, the Stiletto Cocktail is the perfect libation to help ease you into the colder months while still holding on to the last strings of more carefree summer days.

A quick online search for information about this drink will yield widely varying results. Apparently there is not one “recognized” recipe for the Stiletto cocktail – people simply grab the name and slap it on just about anything apparently. Some of the recipes you find online for this drink are served in martini form, a few as shots, and many in old fashioned glasses. You find that some of the recipes call for fruit (such as blackberries), some have bubbly, and a couple even call for scotch.  That being said, I found that most Stiletto recipes share 3 common ingredients: whiskey, amaretto, and a citrus element.

Stiletto-Charlie
Even Charlie likes the Stiletto!

The version I had when first introduced to this cocktail was pulled out of Difford’s Guide (my favorite cocktail encyclopedia ever) and it has since evolved into one of my go-to drinks. Difford’s version is actually an unusual twist on the more standard recipe found on the internet, but there are a few additions that make this version a refreshing and delicious treat year round. I find it particularly lovely this time of year though because the bourbon and amaretto have that fantastic nutty, fall/winter feel that is balanced by the more summery element of line. Throw in some cranberry juice and you have a long and tall drink that is hard to resist.

 

Stiletto-top
The Stiletto is one of those cocktails liked by everyone.

Over the years, I have slightly tweaked Difford’s recipe in the cocktail encyclopedia that first drew my fancy and feel this is a great variation. I have also included the more widely used recipe found on the internet for comparison, so I would love to hear your thoughts.

 


Stiletto – Mixed and Mashed version (very slightly adapted from Difford’s Guide)

Stiletto-complete
You can’t go wrong with a Stiletto!

Ingredients:

2 ounces bourbon

1 ½ ounces amaretto

3 ounces cranberry juice

¾ ounces fresh lime juice

¼ ounce simple syrup

Garnish: Lime wedge

Glass: Collins

 

Directions:

Pour all liquid ingredients into an ice filled cocktail shaker. Shake vigorously for 20 seconds and strain into a Collins glass filled with ice. Garnish with a lime wedge.

 


Stiletto-Recipe-2
The more common version of the Stiletto pictured here is still good, but I definitely prefer the previous recipe with lime and cranberry!

 

Stiletto – Common recipe

Ingredients:

1 ½ ounces of bourbon

½ ounce amaretto

½ ounce fresh lemon juice

Garnish: maraschino cherry

Glass: Old-fashioned

 

Directions:

Pour the bourbon, amaretto and lemon into an ice filled cocktail shaker. Shake vigorously for 20 seconds and pour into an old fashioned glass full of ice. Garnish with a cherry.