6 Cocktails Similar to an Old Fashioned

The Old Fashioned is a timeless cocktail—simple and not difficult to make, but impossible to completely replace. There are many different ways to make an Old Fashioned, but most versions start with whiskey, sugar, and bitters.

However, there are many other cocktails that are similarly enduring, and mixed to give you that same sense of class and tradition. Here is a list of “old fashioned” cocktails, the combination of ingredients that create the taste, and some tips on how to best enjoy them.

The Manhattan

It’s pretty much agreed that the Manhattan is the closest relative to an Old Fashioned: both date back to the 1880s and both are strong, simple, and whiskey based.

The Manhattan has replaced the sugar cube with an ounce of sweet vermouth! It will keep its whiskey taste but the “sweetness” will be different.

They’re also served differently: the Old Fashioned should keep its traditional tumbler and large ice cube, while the Manhattan is typically mixed and then poured into a cocktail glass.

Garnishes differ too. The Old Fashioned is finished with orange peel, and the Manhattan a brandied cherry. The Manhattan is a cocktail hour drink, clean and lean, and you can try out a recipe right here.

The Mint Julep

The Mint Julep is a bourbon based cocktail which originated in the American South and is associated in particular with the Kentucky Derby. It’s cold and clean and maintains that classic simplicity which keeps the “old fashioned” cocktails so popular.

The Mint Julep is made with bourbon, mint leaves, sugar syrup, and ice, muddled gently, and served very very cold.

The Julep is served in a highball glass, or even better, a julep tin, to keep it colder for longer, and is garnished with fresh mint.

There are many varieties of the Mint Julep, mostly achieved by adding to the base alcohol. The Ginger Mint Julep, for example, is made by adding a ginger liqueur and is also popular as a summer evening refresher.

The Roosevelt

The Roosevelt swaps rum for the whiskey and a little dry vermouth, which is shaken and stirred through with some orange juice and a simple sugar syrup, and finally garnished with a twist of orange.

This is a balanced and striking cocktail, kind of dry and kind of sweet, depending on who’s making it. Its history seems to date back to its status as a welcome home drink for Roosevelt after a fifteen-month expedition taken in British East Africa.

The Roosevelt is best served in a chilled cocktail glass, and the orange juice should always be fresh. You’ll find it sweet, but not sticky, and that it will add a refreshing lilt to the end of a long day.

The Brandy Old-Fashioned

A lovely and simple old school brandy cocktail! This one features brandy flavored with a sugar cube which has been soaked in bitters and muddled with orange and cherry.

The final drink is fizzled up with a generous splash of lemon/lime soda and chilled with a large ice cube.

Enthusiasts claim that brandy adds “dimension” to an Old Fashioned, and by this, they mean that a cocktail is eventful. This is important: it means there is more to your drink than just flavor.

You can try this one for yourself here—it has the reputation of being one of the best brandy cocktails there is.

The Negroni

The Negroni is a classic Italian old-fashioned cocktail made with gin and vermouth and is popular for its air of style, elegance, and nonchalance—but at the same time, simple!

The Negroni originated in Florence, Italy, in the early 1900s and when made in the traditional way, was built over ice in an old fashioned glass and garnished with a slice of orange or orange peel. Negronis are still made this way.

The recipe also includes Campari, which is an Italian aperitif liqueur, and Negroni fans stress the importance of good quality ingredients that are balanced in proportion.

The true flavors of a Negroni are sweet and citrus, but if made with skill, the bitter notes will also come out to play.

The Young Laddie

Ok, so this one is created with Scotch, and uses two types of bitters to make a cocktail that is definitely eventful. Each recipe will probably recommend the Bruichladdich Scotch with a classic gum syrup and then bitters, one of which will be grapefruit, the other Peychaud's.

The cocktail is garnished with orange and grapefruit twists which are squeezed over the drink before being dropped in.

If you don’t have grapefruit bitters, enthusiasts recommend Angostura as a substitute, and you can also elevate the cocktail to a Young Laddie Sour by adding lemon juice and garnishing with lemon zest.

The original Young Laddie was invented by Joaquin Simo (Bartender of the year, 2012) of Death & Co in Manhattan.

Note the simplicity and strength of its build, which is why it lines up so well with the rest of the Old Fashioned crew.

What do all of these cocktails have in common?

You may be noticing certain features that are common to all of these (and many other) timeless and traditional cocktails:

  • The relatively small number of ingredients needed in each recipe
  • The strong and unique (or “punchy”) flavor profiles of each ingredient
  • Clarity of design and build
  • Nothing murky, nothing slushy, nothing artificial and everything fresh
  • The significance of the server ware: glasses are old fashioned and chunky or sleek and traditional and always served chilled
  • They all satisfy the need for the classic: less complex, less busy, less convoluted, and less risky
  • “Sweetness” is subtle, and never becomes saccharine
  • They all respond well to quality ingredients

Finding a single cocktail you really appreciate and always want brings the risk that one day, you won’t be able to get one or the bartender won’t be able to make it.

However, if it’s the Old Fashioned that you like and want to investigate further, these are some of my favorite cocktails that embody the old-style, the timeless, and the classic.