4 Classic Gentlemen's Cocktails

You walk into a bar on a Saturday night to meet your friends. It's a nicer place and you fit right in. You've got on a killer outfit, you've taken the time to groom yourself to a tee, and you're feeling great. You approach the bar and hear the question you knew was coming, yet still were somehow unprepared for. "What would you like to drink?" You stare back blankly and choose the first drink that comes to mind: "I'll have a rum and coke." 

"I didn't really want that," you say to yourself. Don't you wish you'd have thought about this beforehand so you could order a drink to match your attire? Today we're going to teach you about the 4 classiest gentlemen's cocktails, how to order them, and how to make them for yourself.


The manhattan is one of the classiest cocktails out there. Invented in the 1870s, this drink has it all. It’s simple, it lets you enjoy the flavor of the spirit and it looks cool when you’re drinking it. This is a cocktail that you could order anywhere and it will never be out of place. Walking around a crowded city bar in shorts and a polo shirt? This drink just made you look even cooler. Wearing a suit at a cocktail party? This drink fits the part. It’s a great way to enjoy a fine liquor without hiding its flavor behind sugary mixers.

How to Order a Manhattan

When you order a manhattan you’ll need to know what kind of liquor you want. It pairs well with either a bourbon or a rye. Approach the bartender knowing which you’d prefer and you can either choose a brand you like or have the bartender choose one if you like to trust their judgement.

Recommended Spirits

  • Bulleit Rye: This is actually my go-to Rye on its own, and it happens to go very well in a manhattan as well.
  • Maker’s Mark: This is a nice strong bourbon with a great finish that makes for an excellent Manhattan.

How to Make a Manhattan

  • 2 oz rye or bourbon
  • ½ oz sweet vermouth
  • 1-2 dashes bitters
  • Maraschino cherry or lemon twist to garnish


The martini is the drink of choice of James Bond. If that doesn’t make it cool by itself, it also comes in a unique bird bath-shaped glass that’s sure to stand out in a crowd. A man that drinks a martini is a man with an appreciation for the finer things in life.

The martini was originally invented as a Gin cocktail, but has since expanded to e a vodka cocktail as well. If you order a martini, chances are it will come with gin unless you specify otherwise.

How to Order a Martini

Martinis have a bit of lingo associated with them that may throw you for a curve if you don’t know what you’re asking for. Don’t worry, we’ve got it all laid out for you.

Begin your order by specifying whether you want vodka or gin. Choose your brand if you have a preference.

Here’s where the lingo comes in.

Wet, Dry, or Extra Dry?

A wet martini means it has a lot of Vermouth in it. Dry means it’s a medium amount of Vermouth, and extra dry means it’s a very faint trace of vermouth in the drink. If you order extra dry the bartender may just wet the glass with vermouth and pour it out before adding the gin to the glass.

Would You Like it Dirty?

A dirty martini comes mixed with some olive juice or olive brine. This will cloud the look of your drink and add a potent complexity to the taste.

On the Rocks, Neat or Straight Up?

This terminology applies to more than just a martini but it applies to the martini nonetheless. Rocks means it will come served over ice. It will stay chilled longer, but will dilute as the ice melts. Neat is basically just poured out of the bottle into the glass. No chilling whatsoever. Straight up will come poured out a shaker filled with ice so the drink is chilled but the ice remains in the shaker.

It’s a bit complex overall, but your martini order should be designful and simple. Here’s an example of a simple martini order.

“I’d like a dry Hendrick’s (gin) Martini straight up, extra dirty.” You’ve just ordered a gin martini with Hendrick’s Gin, shaken over ice with vermouth and extra olive brine.

Recommended Spirits

  • Tanqueray Gin: This is a London dry gin, and happens to be family’s drink of choice for martinis and Gin and Tonics! It makes for an amazing cocktail with a it of that extra Juniper taste.
  • Ketel One Vodka: Ketel one is a great vodka for a martini. It’s smooth and simple with a great flavor for pairing with that splash of dirty if you like it.

How to Make a Martini

  • 2-½ oz gin or vodka
  • ½ oz dry vermouth
  • Olives for garnish
  • Optional: splash of olive brine

Old Fashioned

The old fashioned is a very early bourbon cocktail that originated in the 19th century. It expertly mixes the smooth taste of bourbon, some bitters, and citrus with just a hint of sweetness for a versatile cocktail that you can have in many different ways. It’s even believed that this drink originated as a breakfast drink, though we don’t condone starting your day with a strong liquor.

How to Order an Old Fashioned

Old Fashioneds come in all shapes and forms so you’ll need to know exactly what you want to make sure it comes out the way you like it. First choose between bourbon or rye, and specify a brand if you prefer one. The garnish is where it can vary widely. Some people want a slight hint of citrus from orange bitters, other want the actual citrus. If you want a stronger citrus flavor you’ll want the fruit to be muddle in the glass prior to mixing. You can have cherries or oranges muddled in the drink, or simply garnish it with a lemon twist.

Recommended Spirits

  • Rittenhouse Rye
  • Bulleit Bourbon

How to Make an Old Fashioned

  • 2 oz bourbon or rye
  • 3-4 dashes bitters
  • 1 tsp simple syrup (1 part water, 1 part sugar shaken vigorously until it becomes a solution)
  • Splash of soda
  • Optional: Cherry or orange slice for muddling, or lemon twist for garnish

Mint Julep

A Mint Julep is quite possibly my favorite summer drink. I used to think bourbon was meant only for the colder months, but this cocktail is the absolute perfect summer cocktail. This is one of the oldest recipes on our list, originating sometime in the 18th century in the southern United States, and it’s now the official drink of the Kentucky Derby as of 1939.

How to Order a Mint Julep

The mint julep is very straight forward. Simply order it and select a bourbon. It’s typically recommended you stick with a kentucky bourbon to stay with mint julep tradition. You may choose to specify how strong you want the mint flavor or how sweet you want it, but the house usually makes it well.

Recommended Spirits

  • Knob Creek Kentucky Bourbon
  • Buffalo Trace Kentucky Straight Bourbon

How to Make a Mint Julep

  • 10 mint leaves, plus a sprig for garnish
  • 1 1/2 teaspoons superfine sugar
  • Seltzer water
  • Crushed ice
  • 2 1/2 ounces Kentucky bourbon whiskey

Learn these 4 drinks and you’ll have a great repertoire of classic gentlemen’s cocktails to aid you whenever you’re hoping to look classy at the bars or just have a classy night in. By the way, while we call these gentleman’s cocktails, that does not mean they are exclusively reserved for men. Women can and do enjoy these cocktails frequently. These are just the ones that we think are associated with the classic gentlemen of the times of old.

Have any questions, comments or concerns? Join the discussion below in the comments or reach out on Facebook, Instagram, and Twitter! You can always reach out via email as well at hello@thegentlemenslounge.co.

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