Shopping for the boss is tricky. It’s important to demonstrate a certain level of esteem for the person who signs your paychecks and approves your last-minute vacation day requests, but you don’t want to be overly familiar, either.

Spending is similarly fraught. Skimping seems unprofessional, yet overspending could give the impression that you don’t need that raise you plan to solicit at your review next month.

With these concerns in mind, we’ve created a list of gifts perfect for your supervisor, from big-ticket items to understated objets that work hard for the money.

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You’re New at the Company and Want to Keep it Casual

bottle opener

Your boss may already own a bottle opener, but we guarantee it’s not as cool as this smart midcentury number made from acacia wood. It’s the perfect way to demonstrate your excellent judgment without going overboard.

Your Boss is Friendly but Not Exactly a Friend

decanterA chic decanter plus an accessible bottle of wine is thoughtful but not overly intimate. Not sure what the boss likes to drink? Don’t overthink it. Get a Pinot Noir. It’s crowd-pleasing and pairs with most holiday menus.

Your Boss Was at Your Wedding

Champagne bucketThis copper Champagne bucket is the sort of thing everyone wants but no one has. If your boss is a Champs fiend, gift it with a nice bottle of bubbly. Alternatively, fill it with potted greenery or bulbous chrysanthemums. (The interior is stainless steel, so you can go full Pinterest with impunity.)

Your Company Does One of Those Terrible ‘White Elephant’ Things

socksBasic usually wins. Depending on spending limit, go with either a gift card or these clever socks, a one-size-fits-all solution to most problems.

You Work for Someone Who Self-Identifies as a Millennial

flaskA well-designed, gender-neutral flask. Depending on the level of millennialism we’re talking about, you could opt for a unicorn flask.

You Work for Don Draper or a Don Draper Type

whiskey decanterA classic whiskey decanter never goes out of style. If your boss regularly shouts “I need ice!”, you should probably seek employment elsewhere because that’s rude and you deserve better. If it’s somehow charming and you’re O.K. with it, these soapstone whiskey spheres look pretty rad in a rocks glass.

You Work for Olivia Pope

coasterShe’s already got the Burgundy wine glasses. Consider these sophisticated wine bottle coasters, which fit snugly around most Burgundy, Bordeaux, and Champagne bottles, and prevent red-wine stains on light or white fabrics.

Your Boss Shops at the MoMA Design Store

pitcherEarnest Studio & Emile Pallard created a sleek, multi-purpose design objet that hasn’t already been gifted by every Monocle subscriber a million times. A combination pitcher and watering can, it comes in a surprisingly neutral shade of mint.

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