There are two kinds of people in this world (or three kinds, including people who try to defend Star Wars Episodes 1 through 3). But among drinkers, there’s the kind who’ve had an Old Fashioned, and those who haven’t.

Within those categories are further subdivisions: those who’ve not only had an Old Fashioned cocktail, but have a particular, ardent preference (bourbon or rye), and inevitably a particular, like Boy Band crazy, brand preference. And then there are those who’ve ordered an Old Fashioned because the mixologist wore suspenders and stared at them with a mixture of hope and sexy impatience. “Old Fashioned, please! Ahem. I love jazz. Anyway. But yeah, an Old Fashioned…” Sounds cool, drinks well, earns speakeasy street cred.

And with good reason. The Old Fashioned is a “cocktail” in the truest, most original sense of the term—basically a sugar cube, a splash of water, a couple of dashes of bitters, and 2 ounces of whiskey, it’s still rich and silky and complex like Jared Leto, despite being so apparently Spartan.

Since the Old Fashioned is basically booze, sugar, Angostura bitters, and ice, the whiskey matters. A lot. Not to overwhelm—since whiskey can do that—the main factors we’re looking for are either a bourbon that isn’t too sweet, a rye that isn’t too spicy, and a whiskey that’s sufficiently high proof and dry to withstand both the sugar cube and ice dilution. Bear in mind, since an Old Fashioned is a mixed drink, you don’t wanna break the bank on either bourbon or rye. Buy decent, but don’t buy extravagant—save that for thoughtful sipping.

And then, yes, find a classy fedora to wear while drinking it, doing your best Don Draper/Peggy impersonation. Peggy wore fedoras, right?

Bulleit Straight Bourbon Frontier Whiskey

Bulleit Bourbon is a great whiskey to use in an Old Fashioned

With a higher rye content, you’ll get a better balance between sugar and whiskey, with drying, fruity rye keeping the smooth, sweet corn (the Bourbon factor) in check and giving the Angostura plenty of room to swim around.

W.L. Weller Special Reserve

W.L. Weller is a great whiskey to use in an Old Fashioned
This will tend you toward a slightly smoother, sweeter Old Fashioned—but why judge yourself? You like it sweet and smooth, so go there. With generous honeyed notes of a rich, barrel-aged bourbon, you’ll wish you were on a riverboat.

Buffalo Trace Bourbon – BEST OVERALL

Buffalo Trace is a great whiskey to use in an Old Fashioned

A balance of corn and rye, with more corn (sweetness, caramel, vanilla notes) after aging. You’ll get a smooth Old Fashioned with some subtle hints of spice. An added bonus: this is often the bourbon craft cocktail bars use for their traditional Old Fashioned.

Four Roses Small Batch Kentucky Straight Bourbon Whiskey

Four Roses is a great whiskey to use in an Old Fashioned

“Small batch” may not be a legal term, but what you’ll find in the Four Roses bottle will taste spot-on. Caramel, butterscotch, undercut by spice and a prickle of red berries.

Eagle Rare Kentucky Straight Bourbon Whiskey

Eagle Rare is a great whiskey to use in an Old Fashioned

Don’t confuse this with Eagle Rare Single Barrel—that’s likely better to sip on its own (since it’s not a blended bourbon, just the “one time only,” idiosyncratic expression of a barrel). But Eagle Rare 10 Year will give you one of the more luxurious experiences of a bourbon Old Fashioned, with a subtle depth of flavor that wouldn’t (shouldn’t) be expected for the price.

Jim Beam White Label Bourbon Whiskey – BEST BUDGET OVERALL

Jim Beam is a great whiskey to use in an Old Fashioned

Considering it’s been made with the same formula since the late 18th Century, it must be pretty good. Not as deep as other bourbons, but consistent, smooth, spicy—maybe the ideal affordable bourbon to mix with.

Rittenhouse Rye

Rittenhouse Rye is a great whiskey to use in an Old Fashioned

Here’s some truly affordable rye character. A bit more pluck than a classic bourbon, with distinct notes of pepper and subtle fruit to round it out. Oak notes, with caramel and spice, edge out a dryer finish. A bracing spirit, capable of holding its own against sugar cubes, water, or just a long day.

Old Overholt – BEST BUDGET RYE

Old Overholt is a great whiskey to use in an Old Fashioned

Old Overholt is certainly the stuff Don Draper drinks (at least once), but it’s also just a great entry-level rye, affordable (should be under $20) but not weirdly “cheap,” with balanced and a bit less prickly, rye notes swirling around a smoother body.

Sazerac Straight Rye Whiskey

Sazerac Rye is a great whiskey to use in an Old Fashioned

Rich, lustrous, exotic, spicy—you can kind of keep complimenting this rye for a while and it won’t get embarrassing. Sip before you mix, and drink the Old Fashioned you make with it slowly.

Old Potrero Single Malt “18th Century Style” Rye Whiskey – BEST RYE SPLURGE

Old Potrero is a great whiskey to use in an Old Fashioned

A single malt rye (meaning the rye has been partially germinated) made in the 18th century style—a lighter char, almost a mild toasting, on the barrel—meaning you’ll get a lot more delicate (but 100% rye) notes. Spice and light fruit and tawny wood. Also good to sip, but absolutely spot on for a rye fiend’s Old Fashioned. (Cuz why not?)