Gift Ideas for Supporting Players: An Etiquette Expert Weighs In

Classic holiday quandary: You want to express your gratitude to all the wonderful people in your life, but you’re not sure how big of a gesture to make. (Plus, your gifting budget isn’t exactly bottomless.) To your rescue: etiquette expert Annie Dean, who has tips on navigating this tricky social terrain. From the dry cleaner who can fix the most harrowing stains to the cool coworker who keeps you sane in your cubicle, Dean has tips for giving to everyone in your outermost circle.

The Co-worker

She’s the friendly cube-mate who's always willing to cover for you (and unwind over a cocktail after work). You want to show her that you’re grateful for all of the Excel shortcuts she’s taught you, but you don’t want her to think you expect a gift in return. Dean recommends a thoughtful yet affordable item, like Jouer’s Sparkle & Shine Holiday Cracker, which pops open to reveal a mini lip gloss and other treats. For a guy, we like Areaware’s cool-looking Fort Standard Corkscrew. Don’t be fooled by the elemental design—there’s some serious functionality built in.

The Boss

Opt for a gift that shows you have great taste but that isn’t too expensive or too personal, says Dean. For a female boss, TOCCA’s Exclusive Cleopatra Body Set is luxurious without being over-the-top. Report to a man? Try würkin stiffs’ magnetized Power Stays. They’ll make him feel thoroughly appreciated (not to mention dapper).

The Superintendent

Word to the wise: Butter up your super with a seasonal tip, and we guarantee you’ll get a quicker response the next time you have a jammed doorknob or leaky faucet. (Also, it’s the right thing to do.) If your super is regularly coming to your apartment to help out with repairs, Dean suggests tipping between $50 and $100. Sweeten the deal with homemade cookies or, if you’re low on time, store-bought chocolates—we’ve tried Ghirardelli’s new Toffee Crunch or Mint Cookie bars and they’re mighty tasty.

The Landlord

Your landlord isn't expecting a tip—after all, aren't you the one paying the overpriced rent? However, if you feel like making a neighborly gesture of goodwill, drop off a bottle of wine with a card saying how happy you are in your home, says Dean.

The Dog Walker, Babysitter, and Favorite Dry Cleaner

For the part-time but regular service people in your life, the tip amount comes down to percentages, says Dean. Tip your dog walker the equivalent of one week's pay, your babysitter the equivalent of one night’s pay, and for your ingenious stain-conquering dry cleaner, an extra $20 should suffice, For a more personal feel, spruce up your gift with small but thoughtful extras like a set of organic lip balms from S.W. Basics.

The Teacher

A small, simple gift is key where grades are involved, be they your own or those of your children. For a low-cost treat that will look and taste decadent, spring for Ahmad Tea’s Brittania Collection or Fatty Sundays’ Chocolate Pretzels.

The Sibling S.O.

When your brother or sister takes the leap of bringing someone home for the holidays, you want to be welcoming without seeming overbearing. Hit the right note with something small and sweet, says Dean. We love JONATHAN ADLER’S Boot Socks for a guy. And any lady will welcome the chance to escape and hit the tub with one of Mox Botanicals’ Bath Soaks.

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