The Tuxedo No. 2 is nearly as old as the tuxedo itself: Both are said to draw their names from Tuxedo Park, an upstate community for the New York City elite established in 1886. The first Tuxedo cocktail, which likely originated at the Waldorf-Astoria hotel in New York City, comprises a mix of gin, sherry, and orange bitters. The Tuxedo No. 2, however, omits the sherry and adds a touch of maraschino liqueur and an absinthe rinse. In fact, despite its name, the second Tuxedo bears more similarities to the Turf Club, another turn-of-the-century Martini variation with maraschino liqueur, absinthe, and orange bitters. Alongside this variation, the first written recipe for the Tuxedo No. 2 appeared in Harry Johnson’s Bartender’s Manual in 1900.
Fast-forward to more than a century later, and the Tuxedo No. 2 had been largely forgotten. That changed a few years ago, when bars like the Douglas Room in San Francisco and the now-shuttered Flora Bar in New York City resurrected the drink.
This particular version comes from the latter. Old Tom gin is the backbone of the classic, but slightly drier Plymouth gin makes for a more modern version. Although it isn’t quite as soft as Old Tom, it strikes a good balance between that and a London Dry. Even those who prefer their Martinis bone-dry will appreciate this drink’s simple deliciousness. Opt for a high-quality maraschino liqueur, a crucial ingredient in many beloved classics like the Hemingway Daiquiri, the Aviation, and the Last Word. It lends the drink its characteristic sweetness and notes of cherries and almonds. An absinthe rinse offers a distinct herbaceous anise note, and reaching for a blanc vermouth rather than dry is essential. Should you use dry, your results will lean closer to the Turf Club, which employs dry vermouth and a more juniper-forward gin. The Tuxedo No. 2 is also similar in flavor to the Martinez, which swaps blanc vermouth for sweet and orange bitters for Angostura.

Référence: https://www.liquor.com/tuxedo-number-2-cocktail-recipe-5217855