Grab a small, shallow plate that will fit the entire rim of your martini glass. Fill the plate with vanilla frosting, concentrating on the edges to make a thick wheel of frosting.

Hold the martini glass upside down, by the stem, tipping it into the plate of frosting. Dip and twist to evenly coat the rim of the glass.

Fill a similar plate with crushed gingerbread cookies or graham crackers. Again, hold the martini glass upside down by the stem, dipping and twisting the frosted rim in the cookies until evenly coated.

Set aside for later.

Add whipped cream vodka, coffee liqueur, milk, softened ice cream, and gingerbread syrup to a cocktail shaker filled with ice.

Shake until very well mixed and frothy. You want to make sure the ice cream is very well incorporated and you get a nice froth on top of your martini.

Strain into cookie rimmed martini glass.

Top with whipped cream, a gingerbread cookie on the rim, and a pinch of cinnamon.