MIXING TOOLS
Sometimes used as a measurement for syrupy ingredients—e.g. “one bar spoon of pomegranate syrup”—its main purpose is to stir drinks; around 12.5 inches is the standard length for your standard-sized mixing glass. Too short and your sleeve cuffs will be taking alcohol baths. Too long and you'll look like Pee-wee Herman mixing a cocktail.
Buy the Boston type, in which you hold together two parts that look like metal pint glasses. You can make all shaken drinks in these. Skip the cobbler-type with the built-in strainer and cap. It can't do anything better than the Boston shaker, except look a little cooler.
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The Hawthorne is your go-to tool for separating cocktails from extraneous ice and ingredient remnants as you pour from a mixing glass or shaker. It fits against the rim of both like a lid.
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Japanese jiggers weren't originally Japanese, but when Western bartenders rediscovered their Japanese counterparts using them in the 2000s, they fell back in love with the two-sided measuring tools. They have different capacities on each end, so you can buy half as many as you'd otherwise need. First get a 1-ounce x 2-ounce jigger.
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There's also the option to get all the tools you'll need—and a few that you won't—in one haul. This cocktail set comes with a stand, which is a nice flourish, though the individual tools aren't quite as well-made as those piecemeal options above.