The Rule of Three

During the halcyon, overserved and overjoyed run that is the wedding years - that spate of time in one's late 20s in which one's social calendar is seemingly filled to the brim, for a handful of years on end, with weddings and the attendant pre-ceremony celebrations (Engagement Parties, Bachelor Parties, Rehearsal Dinners, and the like) - nights on the bottle, and the hazy-at-best memories of them, tend to run together.

This is especially true for those of us who came of age, mercifully, prior to the Digital Age. Without constant public-facing digital documentation of each and every moment, regrettable or otherwise, many occasion/incident-specific clarity was lost to the ether. But for me personally, one night in particular stands out as one in which I, quite ironically, truly learned what it means to drink like a gentleman.

In the early aughts, huddled into a stark, minimally-adorned, nondescript room of no more than 500 square feet, set somehow entirely inconspicuously two floors above Boston's most heavily-trafficked cavalcade of bars and nightclubs (ahhh, "The Alley"...), about a dozen of us and our significant others sat peering inquisitively around what looked like the childhood clubhouse of an Ivy League Brahmin brotherhood (which it actually turned out to be). It was there that the decidedly un-raucous father-in-law-to-be of my best friend and former college roommate was hosting an increasingly raucous celebration of the engagement of his daughter to the aforementioned friend/former roommate.

Given the pedigree of the host - a distinguished, eminently genteel Harvard man, rather famous New York City architect, and truly the epitome of gentlemanly manners in every possible sense - and his own former college roommates, all of whom were cut from a similarly high thread count cloth, we all felt a combination of curiosity (as to what "scene" could possibly unfold in this setting) and unease (as to how we might curtail our own still-rather-rabid appetite for a party, so as to not offend the buttoned up elders among us). Then out came the cocktail shaker. 

Not just any cocktail shaker, mind you. While not quite emanating a blinding light like whatever was housed within the suitcase in Pulp Fiction, this behemoth certainly imbued the surroundings with a palpable presence befitting its heirloom (as we later learned) status.

It was huge. And beautiful. Roughly two feet tall if it was an inch, it was made of quarter inch thick, vertically ribbed glass, with a sterling silver domed top roughly the size of Andre the Giant's yarmulke, engraved with the names of several generations of members of these particular gentlemen's Harvard social club, in whose approximately 120 year old secret clubhouse we (again, later learned) were celebrating. Had to have weighed about 7 lbs empty. In it, were made the Daiquiris.

Now, having been reared in the era of blender-made, slushy sugar-bomb 80s tiki delights of the same name, hearing navy blazer clad Mayflower lockjaws proudly heralding the magic-making Daiquiri-based powers of this particular shaker was at first tough to process. Almost as tough to process as the initial sips of the utter jet-fuel-grade combination of the three - and only three - ingredients: overproof rum, lime juice, and simple syrup. It was truly incongruous.

Of all the cocktails these well-heeled titans of industry could have enjoyed, of all the ingredients at their disposal, of all the various successes and milestones their lives had to celebrate, they chose this simple, humble drink. Three ingredients, some ice and elbow grease. And from it hundreds of years of joyous, gentlemanly (at least at the outset) celebrations.

And therein lied the lesson. For the shaker wasn't there, despite its size, to accept 20 different artisanal, micro-sourced ingredients as the craft cocktail trend would later usher in. Just the three. But like the recipes for the best nights themselves (we would all later learn), the best drink recipes are simple, unadorned, and time-tested. All you need is three.

As the evening wore on, the simplicity of this cocktail, and the quality of its ingredients, really stood out. And with that, the wisdom of a stripped down formula in general. As countless hundreds of bar-goers and club kids and otherwise ambled about aimlessly two stories below us, a scene in which we all would normally have reveled, we were perfectly happy ensconced in a ratty old room, drinking powerful booze with a bunch of powerful old men, from a cocktail shaker that was older than most of our great-grandparents. And we loved it. We learned then and there that even in our mid-20s, we didn't need a $20 door charge and a famous DJ and a "scene" full of strangers to have a blast - all you need is good friends, good booze, and a place to laugh. Just the three.

The same Rule of Three rings true with the sartorial elements of the Preppy uniform: navy blazer, oxford button down, chinos. As with a well made navy blazer, etc., through which the quality of the materials, and the impeccability of the make, and the attention to detail of the designers and tailors take an also-ran garment to exquisite, tasteful heights, simple cocktails, like simple get-togethers with good friends, embody the gentleman's ethos to a T. Take a simple concept, gather the finest component parts, execute it to the most thoughtful, highest level of quality possible, and enjoy for generations. It's what we do every day with our heirloom quality, luxury menswear. And what we do when ordering a round as well.

So when it comes to a gentlemanly tipple, leave the muddled fruit and smoked sea salt and basil foam to the hipsters. Whether the Old Fashioned, the Negroni (or their distinguished middleman The Boulevardier), or the ever-venerable Daiquiri, the most gentlemanly cocktails follow the Rule of Three.

If you are aching for variety, swap out one ingredient for another (mezcal replaces rye in warmer months for me), or change up the ratios if you need more (or less) of a punch. But keep in mind the old adage: Gentlemen keep it simple. Gentlemen do it right.

À santé...


Old Fashioned
1 sugar cube (or teaspoon of simple syrup)
3 dashes bitters (muddled together)
2 oz rye (bourbon if you must)

Add ice, stir in glass, garnish with rolled orange peel (rocks)

1 oz gin (swap out for rye for a Boulevardier)
1 oz sweet vermouth
1 oz Campari (or other bitter liqueur)

Add ice, stir in glass, garnish with rolled orange peel (rocks)

2 oz silver rum (or rhum agricole, if you are feeling adverturous)
1 oz fresh squeezed lime juice
.5 oz simple syrup

Add ice, shake vigorously, strain into coupe (up)