37 Extraordinary Gifts for a Boss Who Has Everything

December 20, 2023 by Melissa Bajda

Finding the perfect gift for a boss who has everything can feel like trying to solve a complex puzzle. It is a delicate balance of professionalism and personal touch, where the usual corporate gifts just won't cut it. Instead, the focus should be on uncovering something unique, something that speaks to their personality or interests, even if they seem to have it all.

We've selected a few gifts that strike this balance perfectly, catering to a wide range of interests and personalities. Each suggestion is crafted to ensure it stands out from the typical fare, providing a thoughtful nod to your boss's unique preferences.

1. Boss Engraved Pint Glass

ThisBoss Engraved Pint Glass is a thoughtful and budget-friendly gift for your boss who has everything. 

This stylish glass is engraved using the sand carving technique, creating a unique and personalized design. With a height of 5.75" and a capacity to hold 16 oz, it's the perfect vessel for your boss's favorite beer or beverage. 

Not only is this pint glass a practical gift, but it also adds a touch of elegance to any drinkware collection. And the best part? It's one of the best gifts under $25!

2. Scotch-Infused Toothpicks Gift Set

Elevate your boss's snacking experience with theScotch-Infused Toothpicks Gift Set

These toothpicks are infused with the flavors of fine single-malt scotch, adding a sophisticated twist to their post-meal routine. Each set includes four different flavors, allowing them to sample a variety of scotch profiles. 

Whether they are a whiskey connoisseur or simply enjoy the finer things in life, these toothpicks are sure to impress. It's a unique and thoughtful gift that will make their tastebuds sing.

3. Funny Super Boss Portrait

Turn your boss into a superhero with aFunny Super Boss Portrait. This personalized and comical artwork will have your boss laughing out loud. 

Choose a photo of your boss and the portrait will be transformed into a humorous superhero illustration, complete with a cape and mask. It is a unique and lighthearted way to show your boss how much they mean to the team. 

Hang it up in their office or give it as a keepsake gift, and watch their face light up with joy.

4. 19th Hole Custom Decanter

This19th Hole Custom Decanter holds 750mL of their favorite spirit and is the perfect addition to any home bar. The glasses are high-quality, heavy, and handcrafted in Wisconsin, USA, ensuring a luxurious drinking experience. 

But what sets this decanter apart is the real Titleist golf ball embedded into the side, adding a unique and personal touch. Your boss will love showcasing this custom decanter and it will surely become a conversation starter at their next gathering.

5. Engraved Carbon Fiber Knife

If you're looking for a gift that will earn you major brownie points with your boss who seemingly has everything? Look no further than theEngraved Carbon Fiber Knife

This sleek and stylish knife measures 8 inches in length and is equipped with a seat belt cutter and window breaker, making it not only a useful tool but also a potentially life-saving one. 

What sets this knife apart is the personalized touch of having your boss's name engraved on the wooden handle, adding a touch of sophistication and thoughtfulness to this exceptional gift.

6. Tears of My Staff Tumbler

Finding a great gift for any boss can be challenging, but theTears of My Staff Stainless Steel Tumbler will impress. 

This sleek and stylish tumbler is not only practical, but it also sends a heartfelt message. With its high-quality stainless steel construction and double-wall insulation, it will keep their favorite beverages at the perfect temperature. 

And the best part? The humorous "Tears of My Staff" engraving on the front will bring a smile to their face every time they use it. Show your appreciation and make your boss's day with this thoughtful gift.

7. Funny Wine Label for Your Boss' Bottle

Add a humorous touch to your boss's favorite bottle of wine or champagne with aFunny Wine Label. 

The "We Might Be the Reason You Drink" label is the perfect way to lighten the mood and show your boss that their hard work is appreciated. With its engaging tone and witty message, this label is sure to bring a smile to their face. 

Simply peel and stick the label onto the bottle for an instant laugh-inducing gift. Cheers to a boss who can handle it all, with a little help from their team!

8. Bullet Proof Whiskey Glass

ThisBullet Proof Whiskey Glass not only holds 10 ounces of their favorite spirit, but it also features a faux 50 caliber bullet embedded in the side, adding a touch of badassery to their drinking experience. 

With its sturdy construction and sleek design, this whiskey glass is sure to become their new favorite. Just remember, it's hand washed only to ensure the longevity of this extraordinary gift. Cheers to raising the bar on gift-giving!

9. Bourbon Barrel Bar Shelf

Transform your boss's home bar with theBourbon Barrel Bar Shelf. Crafted from real bourbon barrels, this shelf adds a touch of authenticity and character to any space. The oak shelf provides ample storage for bottles, while the barrel stave veneer adds a rustic and unique touch. 

The bottom shelf is specifically designed to hold 4 Glencairn glasses, allowing your boss to display their favorite whiskey collection in style.

10. Rustic Wooden American Flag

TheRustic Wooden American Flag is one of the best gifts for your boss who has it all. This hand-made personalized sign comes in three sizes, allowing you to choose the perfect fit for their space.

Whether they prefer an unfinished, gloss finish, or stain (indoor or outdoor), there's an option to suit their style. Plus, the flag can be personalized with your boss's name, adding an extra special touch to this already unique gift. 

With its rustic charm and patriotic design, the Rustic Wooden American Flag will become a treasured piece for their home or office wall.

11. American Flag Wine Rack Holder

Complete your boss's patriotic home decor with theAmerican Flag Wine Rack Holder. This stunning wine rack is made from solid mahogany wood and features a beautiful American flag design. 

It can hold up to 4 wine bottles and comes with 2 matching wine glasses. The rack easily mounts on the wall, allowing your boss to proudly display their wine collection while adding a touch of patriotism to their space. 

With its high-quality craftsmanship and unique design, the American Flag Wine Rack Holder is a gift that will truly impress your boss.

12. Funny Boss Last Nerve Candle

If you're looking for a gift that will lighten the mood and make your boss laugh, theFunny Boss Last Nerve Candle is the perfect choice. This handcrafted candle is made with 7 ounces of soy wax and infused with premium essential oils for a calming lavender fragrance. 

But what sets this candle apart is the hilarious label that reads, "Boss's Last Nerve, Look It's On Fire!" It is the best gift to bring a smile to your boss's face and help them unwind after a long day at the office.

13. Whiskey Crate Gift Set

TheWhiskey Crate Gift Set is one of the best gifts for your boss who has everything this holiday season.

This personalized gift set includes a decanter that can hold up to 25.36 ounces of their favorite whiskey, along with two whiskey glasses that can hold 10 ounces each. The set also includes a set of 9 whiskey stones for a chilled drink, as well as a set of 2 slate coasters to protect surfaces. 

All of these items come beautifully packaged in a cedar crate, adding an extra touch of elegance to this already exceptional gift.

14. Ways to Tell Employees They're Stupid Book

TheWays to Tell Employees They're Stupid Book is the funny gift for a boss with a sense of humor. 

This tongue-in-cheek book is filled with witty phrases and blank lined notebook pages for your boss to jot down their thoughts. It is a lighthearted way to add some laughter to the office and is HR-approved, so there's no need to worry about crossing any boundaries. 

Whether your boss actually uses it or just displays it on their desk, this book is sure to be a conversation starter and a fun addition to their collection of office essentials.

15. Table Top Mini Bowling Game Set

If you want to add a bit of fun and entertainment to your boss's office? TheTable Top Mini Bowling Game Set is the perfect gift for just that! 

This compact and portable bowling game can be placed on any desk or table, allowing your boss to take a break and have some fun whenever they need it. The set includes a mini bowling alley, 10 miniature bowling pins, and a small bowling ball. 

It is one of the best gifts for any type of boss to de-stress and add a touch of excitement to their workspace. Who knew a desk chair could also double as a bowling lane?

16. Good Luck Whiskey Glass

Impress your boss with theGood Luck Finding Better Coworkers Than Us Whiskey Glass. This stylish and elegant glass is the perfect gift for a boss who appreciates a good drink. 

With its 12 oz capacity, they can enjoy their favorite whiskey or cocktail in style. The humorous inscription "Good Luck Finding Better Co Workers Than Us" adds a touch of lightheartedness and will remind them of the great team they have. 

Cheers to a boss who knows they have the best coworkers around!

17. Novelty Cool Fidget Gel Pens

TheseNovelty Cool Fidget Gel Pens are not just your ordinary writing tool. With their innovative design, 13 small steel tubes can be combined into a pen for writing, or they can be manipulated into various shapes to provide a satisfying fidgeting experience. 

Not only are these pens practical for taking notes, but they also provide a fun and stress-relieving activity for your boss during meetings or downtime. Give them a gift that is both functional and entertaining with these best gifts for bosses.

Related: Pen the perfect gesture with engraved pen gifts, a timeless blend of personal touch and elegant craftsmanship.

18. Whiskey Making Kit

Elevate your boss's whiskey game with theWhiskey Making Kit. This kit is one of the best gifts for the boss who loves to experiment and appreciate the art of whiskey-making. 

This Thank-You gift includes everything they need to create their own unique blends, from wood chips and botanicals to glass bottles with wooden corks. With the included recipe guide, they can unleash their inner master distiller and craft personalized whiskey flavors. 

Complete with stainless steel whiskey cubes for the perfect chilling experience, this kit is sure to impress even the boss who has everything.

19. Work Would Succ Without You Succulent Plant

If your boss has a green thumb, go for this! Show your boss how much you appreciate their hard work with theWork Would Succ Without You Succulent Plant Pot. 

This charming ceramic pot, complete with a bamboo tray, is the perfect addition to their office decor. The succulent plant adds a touch of greenery and life to their workspace, while the punny message shows your gratitude in a lighthearted way. 

It is a gift that will remind them every day of the value they bring to the team. Say thank you with these best gifts for bosses.

20. Best Boss by Par Golf Ball on Tee Stand

Impress your golf-loving boss with theBest Boss by Par Golf Ball on Tee Stand. This unique gift is perfect for the boss who enjoys hitting the greens. 

The golf ball features the humorous inscription "Best Boss by Par" and comes displayed on a stylish tee stand. It's a fun and playful way to show your appreciation for their leadership. 

Whether they display it proudly in their office or take it out for a round of golf, these great gift ideas will make them feel like a champion. Show your boss they're the best by par with these gifts for bosses under $25!

21. Conference Call Bingo Mouse Pad

Tired of those never-ending conference calls? Make them a little more entertaining with theConference Call Bingo Mouse Pad. 

This unique desk accessory is not only functional but also adds a touch of fun to your boss's workday. With its engaging design and built-in bingo game, they can mark off those typical conference call phrases and cliches as they hear them. 

It is a lighthearted way to inject some humor into those seemingly endless meetings. Plus, with its 0.20" thickness, it provides a comfortable and supportive surface for their mouse.

22. Leather Valet Tray Box

You know how organized he is. This Personalized Leather Valet Tray Box is specially made for him. Let these desk accessories welcome him each day as he empties his pockets coming home or that last tray he reaches out to for all the things he would need before he goes out.

And each time he does it he remembers you - that’s the best part of it. Customize it with his initials or his name to make it extra special.

23. The Set That Bonds

This is one set of gifts your boss won’t be able to resist. The Set that Bonds gift set comes with a money clip, cuff links, and a tie bar all contained in a box that can be personalized up to 15 characters.

Each item can also be personalized with his name or initials. He will definitely be impressed with these best gifts for bosses.

24. The Wine Guy

Whether attending a gathering with close friends or simply visiting a friend, this Personalized Wine Carrier allows him to handle his wine in style.

Crafted from leather, this wine carrier can hold his standard wine or champagne bottle. It can also be engraved with his name to make it even more special for your 40-year-old boss!

25. Golf Wine Glass

This Personalized and Monogrammed Wine Glass is a gorgeous gift for the boss who is a golf lover. These best gifts for bosses are designed with a golf ball background and name. It can contain up to 19 ounces of his favorite wine.

The background is carved out to leave the monogram raised and have a 3-dimensional effect. It is one gift he’ll proudly show off while having a drink with his favorite buddies.   

26. The Cigar Smoker

His cigars will be kept fresh every day with this Rustic Cigar Box. These best gifts for bosses come complete with a beautiful swing latch and a bed of straw for that perfect presentation.

Specially made of birch plywood, you can have it engraved with his name or initials and you’re all set to hand him a gift he will always remember you by.

27. Cold Brew Coffee Maker & Carafe

Let the boss have his fresh cold brew to go with this Cold Brew Coffee Maker & Carafe in one. Add coarse grounds and a slow, circular pour of cold, filtered water to the top brewing chamber and let it steep for 12 to 18 hours at room temperature.

Then, just press the button and let gravity fill the insulated steel carafe. He may even add ice, his favorite milk, and sweetener. These gifts for bosses under $50 keep coffee cold for up to 24 hours and comes with a leak-proof lid. Pair it with a cool coffee mug!

28. Golf Flask Gift Set

This Golf Flask Gift Set is fun, functional, and comes with a perfect mix of elegance and style. This set includes a round-designed flask that can hold 10 ounces of his favorite beverage. It can even be engraved with a golf ball on a tee and the word “Fore”. 

With two shot glasses and a funnel, he won't lose a drop of his favorite beverage. It's one gift that he'll take on his business trips.

29. Golfer’s Iron Bookend

Organizing stuff and golf are a few of the things he really loves. Give him this Golfer’s Iron Bookend that is crafted from durable iron and features two golfers about to swing propped up on a thick iron base.

It is a functional bookend for his library bookshelf or a cool display on top of coffee tables, a desk, or even end tables. This is one good gift for the boss who loves hitting the greens.  

30. Carraway Monogram Beer Growler

It's a no-no for the boss to endure warm beer. The Carraway Monogram Beer Growler is made of double-walled, vacuum-insulated, 18/8 BPA-free stainless steel that is sure to keep his drinks cold.

He can also use it for other beverages like coffee, which will be kept piping hot for up to 6 hours. This growler can even be personalized with his name, initial, and a custom phrase.

31. Portable Espresso Machine

This Portable Espresso Machine is versatile, compact, and lightweight. It may be used with any variety of hot cup coffee bean/roast, which will give you more flexibility in trying new flavors.

Minipresso GR is your best choice to let him enjoy up to 50 ml of authentic espresso at home, in the office, and on the go.

32. Golfer’s Novelty Desk Gift

He loves golf! This Golfer’s Novelty Desk Gift is a perfect addition to his collection of golf items. It is a quality mini design that includes a pen holder made of soft PU leather and comes with a small zipper storage area that can collect small things like a note, key, eraser, snaps, and many more.

It comes with three different quality aluminum alloy ink pens and a plastic green lawn. The golf cart handle is moveable and can be adjusted to suit any desk. These unique gifts for bosses are something he'll love to see.

Related: If you love the idea of a golf gift for your boss but want more ideas here are some more of our favorites.

33. Portable Leather Humidifier

He travels a lot. But giving him this exquisite Portable Leather Humidifier will make his travel more enjoyable. These best gifts for bosses can hold 5 cigars and comes complete with a humidifier and a hygrometer.

The PU leather outside and the cedar wood inside keep your cigars fresh. It is also packaged in a stylish gift box that your cigar aficionado friend will truly adore.  

34. Golf Cart Cigar Clip

Let him secure his cigar during play with this handy cigar holder. This All-Purpose Cigar Clip will help him manage his cigar while riding or hitting a golf shot.

You can best sure he will never lose his cigar on the green again. The clip-within-a-clip design allows the device to attach to your cart independent of the cigar clip for remarkable stability.

This clip also doubles as a putter stand or golf glove holder for added versatility. Perfect to use during tailgates, BBQ, and any occasion.

35. Desk Dock

Long, tiring days and meeting deadlines are naturally part of his life. He'll appreciate your effort to get his stuff organized the moment he’s home. It includes everything he needs, from phone stand, pen to watch holder.

This Personalized Docking Station is a wooden organizer for his small things like phone, keys, tablet, watch, flash drives, coins, and the like. Have it personalized by having his name or initials engraved on this holder.

36. Collar Concierge

He always exudes looking like a pro and he does it very well. This Tie Gift Set will be perfect as a gift. Arranged in an old-fashioned box, the tie, made up of wool-silk blend, comes complete with cuff links and a tie clip, perfect for 50-year-old boss!

Personalize the gift box with his name and you are all set for giving one amazing gift!

37. Diamond Decanter

This is one gift that will truly impress him. With its amazing diamond shape and elegant look, this Diamond-Shaped Whiskey Decanter will be perfect for him. This decanter can be engraved with your boss' name.

These best gifts for bosses can contain up to 750 ml of his favorite drink like scotch, tequila, rum, vodka, and many more.

Boss Gift Etiquette: Navigating the Dos and Don'ts

When it comes to choosing the best gift for your boss, it's important to consider proper gift etiquette. You want to show your appreciation and thoughtfulness without crossing any boundaries or making your boss feel uncomfortable. 

Here are some dos and don'ts to keep in mind when selecting a gift for your boss who has everything.

Do: Consider Their Interests

Take the time to think about what your boss enjoys outside of work. If they're a wine connoisseur or a golf enthusiast, a gift related to their hobbies would be a thoughtful choice.

Don't: Go Overboard

While it's important to show your appreciation, going overboard with an extravagant gift may make your boss feel uncomfortable. Stick to something thoughtful and within a reasonable budget.

Do: Keep it Professional

Remember that you're buying a gift for your boss, not a close friend. Choose something that is appropriate for the workplace and aligns with their professional image.

Don't: Give Overly Personal Items

Avoid gifts that are too personal or intimate, such as clothing or accessories. Stick to items that can be enjoyed in a professional setting.

Do: Personalize the Gift

Adding a personal touch shows that you've put thought into the gift. Whether it's a handwritten note or a customized item, it demonstrates your thoughtfulness and appreciation.

Don't: Give Generic Gifts

Generic gifts can come across as impersonal and thoughtless. Put in the effort to find something unique or personalized that will stand out and show your boss that you value them.

Do: Consider Their Preferences

Pay attention to your boss's preferences and tastes. If they have a favorite brand or type of beverage, for example, incorporate that into your gift selection.

Don't: Give Generic Gift Cards

While gift cards can be convenient, they can also come across as impersonal. Avoid generic gift cards and instead choose something more specific to your boss's interests or preferences.

Do: Choose a Practical Gift

Practical gifts are always appreciated. Consider items that will be useful in their day-to-day work life, such as a high-quality notebook or a stylish desk organizer.

Frequently Asked Questions

Q1: What gift do you give your boss?

When choosing a gift for your boss, aim for something understated yet thoughtful. A well-made notebook, an elegant desk accessory, or a tastefully selected plant can be perfect. If they enjoy coffee or dining out, a gift card to a quality establishment is a safe bet. The key is to ensure the gift reflects professionalism and respect.

Q2: What to gift a boss on Christmas?

For Christmas, select a gift that’s professional yet festive. Options include an office-appropriate holiday ornament, a premium food basket, or a book by a renowned author in your field. A charitable donation made in their name can also be a thoughtful and meaningful gesture, aligning with the spirit of the season.

Q3: What to buy your boss as a leaving gift?

When your boss is leaving, choose a gift that commemorates your time together. A framed photo of the team, a personalized plaque, or a sophisticated pen set are all excellent choices. These gifts should symbolize your appreciation and the positive aspects of your working relationship.

Q4: What is the best farewell gift for boss?

A farewell gift should be memorable and heartfelt. Custom gifts like a piece of unique artwork, a photo book of team moments, or an item related to their hobbies (like golf accessories or a chef’s knife for a cooking enthusiast) are thoughtful. The aim is to express your gratitude and to leave a lasting, positive impression.


Find the perfect touch for your workspace with Personalized Office Gifts, where uniqueness meets professionalism!

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Curated for the modern achiever: Gifts for the Professional Man, where style meets functionality in the boardroom and beyond.

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Melissa Bajda

About the Author

Melissa Bajda is an gift-giving expert with a decade-long track record of curating gifts that create lasting memories. Her insight into the art of gifting and staying on top of trends by her consistent presence at major gifting trade shows, including her annual participation in NY Now trade show in New York City. With a passion for thoughtful, personalized gifts that truly make an impact, Melissa has built a reputation as a go-to source for unique and meaningful present ideas.

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