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12 Creative Boss’s Day Gift Ideas

October 16 marks Boss’s Day. What should you buy for the person who signs your paycheck? A perfect gift strikes a balance between personal — yet not invasive — and unique without being confusing or weird. Gifts are a way to show your appreciation for your boss’s support and guidance. In addition, if you plan to host a celebratory happy hour or luncheon for your boss, there are plenty of unique venues on Peerspace to consider. That said, take a look at 12 unique ideas to inspire your Boss’s Day gift-giving. Choose one of the following as a stand-alone gift or handpick several to package together.

1. Fancy nut brittles

Annette’s Chocolates by Brent in Napa Valley, California, creates delicious nut brittles with a twist. Choose from beer brittle and chardonnay brittle to bourbon brittle and tequila brittle. However, don’t be alarmed: the infusions of alcohol are careful and add character rather than an overpowering flavor. The shop’s seasonal items, barks, toffees, and truffles are all contained in classic, tasteful packaging and ready to share.

2. Frozen treats from Penn State Berkey Creamery

This the largest university-run creamery in the country, and it’s a world-famous stop on anyone’s Penn State tour. Fun fact: even Ben & Jerry are graduates of Penn State’s Ice Cream Short Course. So, it’s certainly good enough for your boss. Half gallons, pints, and minis are available to be shipped across the country, and they’re packaged in a cooler bag with the precise amount of dry ice for freshness. We recommend flavors like Death by Chocolate or Apple Cobbler Crunch!

3. A nifty bento box

Does your boss have the bad habit of eating at their desk every day? Give them a bento box. They’re efficient to pack, safe to carry without making a mess, and made of environmentally friendly materials. Choose stainless steel, bamboo, or BPA-free plastic varieties.

4. A tempered glass travel cup by KeepCup

Disposable cups are slowly fading from the consumer spotlight, as plastic cups have a hard time keeping the integrity of coffee’s flavor. Not only does glass keep drinks hot — or cold, as the case may be — but it also doesn’t absorb the color or flavor of the beverage. These are great-looking travel mugs that come in custom colors and sizes. Even better, individual components of the cup can be easily replaced.

5. Stemless wine glasses

They come in a variety of shapes, sizes, and designs. What’s your favorite? We love the looks of the Cornet Barcelona Sagrada stemless glass. The Riedel Swirl glass is the perfect gift if your boss prefers red wine. Of course, there’s also the trend of Bodega wine glasses: a small, unpretentious glass meant for casual, friendly gatherings.

6. Wine to help transition from summer to winter

Semillon fits the bill for white wine: it’s full-bodied like a chardonnay but can have flavors such as peach or citrus, like a sauvignon blanc. Beaujolais is a perfect bridge from the pinot noirs and merlots of summer to the bigger cabernets of winter. Alternatively, you can select a syrah or bordeaux blend rosé. Don’t let the fact that it’s pink scare you.

7. BeatsX wireless headphones

Whether used for phone calls or listening to Hamilton during the work day, these Bluetooth headphones are lightweight and comfortable to wear.

8. Amazon Fire HD 8

Your boss probably has a tablet for work, but perhaps not one specifically for personal downtime. With this tablet, your boss can have books, movies, music, and their personal Amazon account all in one place! It’s compact and durable, as well as perfect for storage in a carry-on or handbag for travel.

9. Cozy products, such as a foot warmer or Toasty Toes

Even the friendliest of workplaces have occasional thermostat wars. When feet are cold, everything feels cold! Luckily, foot warmers are easy to use. Place the foot-warming pad at the user’s feet and plug in to a standard outlet. It’s comfortable for most footwear, as well as in socks or stockings.

10. Moleskine notebook and pen

Sometimes typing brainstorms into a notebook app won’t do. Many successful people always have a pen and paper at the ready. Moleskine notebooks are easily recognizable by other great thinkers, in no small part because of the tactile feel of the cover. They come in sizes that will fit in a pocket, handbag, or carry-on, so your boss will never have to be without theirs.

11. Zippo lighter

Consider that Zippos are sharp, reliable, and indestructible. Custom design and colors are available. If the classic windproof design isn’t your jam, there is a more elegant candle variety. A genuine Zippo will last forever.

12. The gift of relaxation

Try a scalp massager tool, Orbits eye stones, or a Gaiam hot/cold foot roller. Is it deeply personal? In a way. But most importantly: would this kind of gift have universal appeal? Absolutely! Ask an accountant at tax time, a surgeon on their feet for hours on end, a software engineer who stares at screens all day long: how would you like a scalp massage/cool eye relaxation/foot rub on demand? The answer would be a resounding affirmative!

When selecting a gift for your boss, think about the environment of your workplace and general vibe of your field. An accounting firm may have different expectations than a hotel sales office. People in tech or engineering won’t necessarily react the same to certain gifts as would people in healthcare. Also, don’t fall into the budget trap: the price point of the gift does not equate value.

In summary


  • Know your audience! Be aware of food sensitivities, personal habits, or political leanings.
  • Be tasteful.
  • Consider their personal style — if you’re giving accessories.
  • Give gifts for the feeling of making another person happy, not to achieve brownie points. It isn’t a contest.


  • Go overboard. It’s Boss’s Day, not Christmas. The gift is meant to be a token gesture. There are very few instances in which expensive jewelry or a pricey bottle of champagne are necessary.
  • Be passive-aggressive — if you hate your boss, either choose a small, inexpensive token or don’t buy a gift at all.

In all, add your personal spin, a simple card, and attractive gift-wrapping. Most importantly, don’t expect anything more from your Boss’s Day gift than a heartfelt “thank you.”

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