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How to Mix a Hard Boiled Shirt

Mixing a Hard Boiled Shirt cocktail

By Chall Gray | Owner of Little Jumbo

I found this drink while doing some some cocktail nerdery, as one does, perusing at old menus in the New York Public Library menu archive from the 1940s.

In doing so, I came across this restaurant menu in Manhattan that had a cocktail on there called the “Hard Boiled Shirt. I thought: What a ridiculous name for a drink. I mean, it is….I also thought, “wow”, because it had bourbon and dry vermouth — and orange bitters in it as a combo — which is interesting because you very rarely see bourbon and dry vermouth combined together. I jokingly shared this find with one of our longtime employees, Matt Smith, and he just thought it was hilarious. So we played around with it and ended up making that drink that we’ve made, which came out pretty good.

We describe this drink as a dry Old Fashioned. What does it mean to be a “dry Old Fashioned”? Well, it’s dry, because the way it sits on your pallet is going to be much lighter and not linger on the velum part of your mouth as much (a.k.a. the “soft pallet”). The Old Fashioned is a cocktail made by muddling sugar with bitters and water, adding whiskey, and garnishing with an orange slice or zest and a cocktail cherry. This cocktail also has that same balance of bourbon and citrus.


  • 2 Oz. Bourbon
  • ¼ Oz Dry Vermouth
  • 4 dashes of Regans orange bitters
  • 1 Lemon Twist


Start with a mixing glass. Measure out and pour two ounces of bourbon — we’re using Four Roses. Then add the dry vermouth — a quarter of an ounce. Then add the quarter ounce of simple syrup, which is just a mixture of one part water and one part sugar. And then we’re going to use Regan’s orange bitters number six — four dashes of that. Then we’re going to add ice and stir. Using an ice strainer for the mixing glass, pour the mixture over a nice chunk of ice in your favorite rocks glass, and garnish with a lemon twist.

Bartenders Notes

When stirring or shaking a drink, we’re looking for a mixture of both chilling and dilution, getting your drink to just the right place of both temperature and taste. Another good rule of thumb for cocktails is that if the drink has citrus, it should be shaken, and if it does not the drink should be stirred.

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