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Boss’s Day Gift Ideas for Every Personality
On Boss's Day, honor your supervisors by giving them a thoughtful token of your appreciation.
Oct 06, 2025
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. (Or was it simply a way for young Patricia to get out of getting her dear ol' dad a birthday present?)
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 10 Boss's Day gift ideas that are a perfect fit for any type of boss (even if he is your dad...).
Fun Gifts for the Laid-Back Boss
Pour them something good.
Fun Gifts for the Laid-Back Boss
Pour them something good.
Shop : Harry & David™ White and Red Wine Duo from Harry & David
Coffee And Bacon Ammo Can from 1-800-Flowers.com
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.
Boss's Day gift for her: A bottle of red and white wine
Boss's Day gift for him: A box filled with bacon and coffee
Shop : Harry & David™ White and Red Wine Duo from Harry & David
Coffee And Bacon Ammo Can from 1-800-Flowers.com
For the Ritzy Boss
Let's be sophisticated.
For the Ritzy Boss
Let's be sophisticated.
Shop : Deluxe Cheese Crate with Wine from Harry & David
Money Tree from Harry & David
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 corner office or complement their luxurious lifestyle.
Boss's Day gift for her: Gourmet Cheese Gift with Wine
Boss's Day gift for him: Money Tree Plant
Shop : Deluxe Cheese Crate with Wine from Harry & David
Money Tree from Harry & David
For the hardworking boss
Revitalize them.
For the hardworking boss
Revitalize them.
Shop : Spa Gift Set - Men's Self Care Kit for any occasion from 1-800-Flowers.com
Appreciation Gift Basket - 100% Natural Citrus Luxury Gift Box from 1-800-Flowers.com
These movers and shakers keep your workplace going, tirelessly working from sunrise to sunset (even weekends!) 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.
Boss's Day gift for her: Appreciation Gift Basket - 100% Natural Citrus Luxury Gift Box
Boss's Day gift for him: Men's Self-Care Gift Set
Shop : Spa Gift Set - Men's Self Care Kit for any occasion from 1-800-Flowers.com
Appreciation Gift Basket - 100% Natural Citrus Luxury Gift Box from 1-800-Flowers.com
For the Innovative Boss
Think inside the box.
For the Innovative Boss
Think inside the box.
Shop : Boarderie™ Ciccetti Cheese & Charcuterie Board from Harry & David
NFL Ventura Portable Reclining Stadium Seat from 1-800-Flowers.com
These guys or gals are always one step ahead of the game; their fresh, new ideas holding the promise of a thriving future. Fuel your boss's creativity by giving them a gift that's as innovative as they are.
Boss's Day gift for her: Boarderie ready-to-eat charcuterie board
Boss's Day gift for him: NFL Ventura Portable Reclining Stadium Seat
Shop : Boarderie™ Ciccetti Cheese & Charcuterie Board from Harry & David
NFL Ventura Portable Reclining Stadium Seat from 1-800-Flowers.com
For the Encouraging Boss
Inspire them.
For the Encouraging Boss
Inspire them.
Shop : Thank You Artisan Belgian Chocolate Covered Strawberries from Shari's Berries
Juniper Bonsai from 1-800-Flowers.com
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 or treat.
Boss's Day gift for her: Thank You Artisan Belgian Chocolate-Covered Strawberries
Boss's Day gift for him: Juniper Bonsai
Shop : Thank You Artisan Belgian Chocolate Covered Strawberries from Shari's Berries
Juniper Bonsai from 1-800-Flowers.com
AUTHOR
Madeline started her writing career as an art and culture reporter for her university newspaper, FSView. She has since contributed to Tallahassee Woman Magazine, CollegeFashion.net, and Mission Magazine. Based in New York City, she enjoys going to art galleries and drinking matcha lattes when away from the keyboard.
