It’s time to celebrate the head honcho with some Boss’s Day gift ideas!

Boss’s Day, which is observed every year on Oct. 16, is a day for employees to acknowledge their managers for all the hard work they do throughout the year. The idea came about when an insurance company employee named Patricia Bays Haroski registered the day as a holiday back in 1958 in honor of her boss — who also happened to be her father. She chose Oct. 16 because it was her father’s birthday, and she wanted it to be remembered as the day that strengthens the bond between employers and their workers.

Nowadays, we still honor our supervisors by giving them a thoughtful token of our appreciation. But how do you pick the right present for the captain of the ship? The first step is to think about their personality and management style.

Here are some helpful Boss’s Day gift ideas that are a perfect fit for any type of boss.

Revitalizing gifts for the hardworking boss

These movers and shakers keep your workplace going, tirelessly toiling from sunrise to sunset to ensure that both you and the company are successful. Give your overachieving boss a gift that will help them relax and re-energize after putting in all those hours.

Fun gifts for the laid-back boss

Business in the front, party in the back! This boss knows how to run a successful operation — and have a good time doing it. For the free spirit with a great sense of humor, give them something unique that will make them smile.

Out-of-the-box gifts for the innovative boss

These guys are always one step ahead of the game. Their fresh new ideas hold the promise of a thriving future. Fuel your boss’s creativity by giving them a gift that’s as ingenious as they are.

Sophisticated gifts for the ritzy boss

Always dressed to the nines and spotted at the swankiest hangouts, this boss lives the high life. Give them something tasteful that will look nice in their big office or complement their luxurious lifestyle.

Inspirational gifts for the encouraging boss

The ultimate team player, this boss has faith in their staff and can stir up your enthusiasm with a motivational speech on the fly. This Boss’s Day, return the favor by presenting them with a spirit-raising keepsake.

Simple gifts for the no-nonsense boss

No frills, no thrills — just show them results. That’s the kind of boss you have, and that philosophy is reflected in their possessions. Get your superior a gift that gets the job done, plain and simple, and doesn’t require a lot of fuss.

Sentimental gifts for the sensitive boss

As someone who leads with compassion and understanding, your boss is in tune with not just his own feelings but those of his staff as well. A gift that hits him in the feels will be much appreciated.


Madeline started her writing career as an art & culture reporter for her university newspaper, FSView. She has since contributed to Tallahassee Woman Magazine,, and Mission Magazine. Based in New York City, she enjoys going to art galleries and drinking matcha latte's when away from the keyboard.

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