16 Thoughtful Gifts That'll Make Your Boss's Holiday

Finish Q4 strong with these creative gift picks.

gifts for boss best 2018

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Bosses can be notoriously tough to shop for. But we did the work for you, so you can cross the toughest person off your list. Here are 15 thoughtful gift ideas to help kick off their holiday break.

1 Echo Dot (3rd Gen) Smart Speaker
amazon.com $49.99

Help streamline your boss's busy life by gifting the newest generation of the Echo Dot. This redesigned tech accessory comes in light, medium, and dark gray, and is bordered by a cloth-covered speaker that'll receive his commands loud and clear. 

Equipped with Alexa's seemingly endless skill set, he can use it to make phone calls, listen to the news, dress for the weather, play games, and so much more.

More: The Best Tech Gifts on the Market Right Now

2 American Bench Craft Premium Leather Cartridge Card Case
kaufmann-mercantile.com $35.00

A coat pocket is no place to stash their business cards or ID when they're on the road. This leather card case makes a thoughtful gift for bosses, since they can use it as either a pared-down wallet or as a card case, and the classic, monogrammable design makes it perfect for virtually any recipient.

3 #1 Boss T-Shirt
amazon.com $24.99

While we can't guarantee that this t-shirt will get you a raise, we can guarantee that your boss will totally love it (and you!) for your flattery and generosity.

4 Heirloom Popcorn Gift Set
shopterrain.com $28.00

Gift them this foodie-friendly gift set so they can bring the corn for popping to their upcoming holiday gatherings! It includes a bag of non-GMO heirloom kernels and a canister of salt, packaged up in a wooden crate to make for one impressive unboxing.

5 Birch Lane Arrow Cheese Markers (Set of Six)
birchlane.com $18.99

They may be well-versed in the art of cheese-board-building, but do they have the right tools for the job? This set of six arrows are each labeled with a cheesy signifier, allowing them to differentiate their sharp cheddar from the more mild selections.

6 Wit & Delight Assorted File Folders (Set of 12)
Wit & Delight



Gift your boss something simple to make her desk a brighter and more organized place. These multicolored file folders from Wit & Delight are a perfect example. They're fun but not too silly, and the manager with an overloaded workspace is sure to put them to good use!

7 Aesop Jet Set Kit
saksfifthavenue.com $37.00

The boss who's traveling home for the holidays (or to some distant, exciting locale) is probably more than ready for a well-deserved winter break. No matter how she's getting there, this unisex toiletry kit from Aesop will give her the first class treatment. It comes with TSA-friendly sizes of shampoo, conditioner, body wash, and lotion, which all smell irresistibly fresh and clean.

8 Zojirushi 25-Ounce Food Jar
amazon.com $29.00

This 25-ounce stainless steel vessel may look simple, but it's packed with food storage potential. Gift it to your boss to ensure his coffee, oatmeal, soup, or other home-brought food arrives safely to work without the risk of spillage. The insulated, leakproof jar is designed with a vent built into the lid to allow users to release the pressure of the contents inside for safer opening in transit.

9 Bushwick Kitchen Threes Knees Spicy Trio
amazon.com $39.99

For the known hot-sauce-loving boss, this trio of spicy condiments makes for one dynamite gift. Bushwick Kitchen's bundle of honey, maple syrup, and sriracha sauce are all spiked with just enough heat to nicely spice up desk-bound breakfasts and lunches.

10 Poketo 2019 Mini Art Calendar
poketo.com $12.00

Here's a holiday gift that'll actually get your boss excited about Q1. This mini calendar is comprised of vibrant, Memphis-design-inspired photos taken by Argentinian artist Eloise Iturbe. It's also just 6 by 4 inches, so it won't take up too much real estate on your boss's wall or bulletin board!

11 Blue Bottle Coffee Gift Subscription
bluebottlecoffee.com $24.00

Give your coffee-obsessed boss a caffeinated gift she won't soon forget! Blue Bottle offers a variety of coffee subscription boxes that start at a reasonable $24. Choose from a variety of sizes and types of coffee, including single origin, espresso beans, blend assortments, and even decaf (what is that?).

12 HTML Beer Glasses (Set of Two)
uncommongoods.com $25.00

If you work in web design, software, or systems engineering, these HTML glasses will definitely get a laugh out of your boss. Pair them with a nice six-pack of his favorite specialty beer (if you happen to know what it is), or choose a neutral option that you know he'll enjoy.

13 College Dish Towel
uncommongoods.com $20.00

If your boss still has a strong sense of school spirit, gift her a handmade dish towel styled in the theme of her alma mater. There are 37 major U.S. universities currently available. If you're not sure what school she went to, check her LinkedIn profile!

14 The Brilliant Ideas Launch Pad
amazon.com $14.95

This notebook isn't just your average college-ruled pad of lined paper. It's full of cleverly designed pages to help your boss bring his big ideas to life using formats like diagrams and workflow charts to get his creative juices flowing. Plus, it doesn't hurt to engage in a little not-so-subtle ego-stroking!

15 Jot & Mark Recipe Card Box
amazon.com $26.99

This recipe tin is a beautiful gift idea for the boss who loves to cook or bake, and it's far more original than getting them a cookbook! It comes with 50 blank recipe cards and 14 dividers. Plus, you can choose from a few different pattern options for the box.

16 Jacobsen Salt Co. Set of Six Vials with Holder
williams-sonoma.com $31.96

Jacobsen Salt Co. makes the most delicious, hand-harvested salts we've ever had and we can't recommend them highly enough as a gift (especially for the boss who loves to cook). This salty six-pack includes sweet onion, habanero, garlic, basil, black pepper, and a flaky finishing salt.

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