20 Gift Ideas For Your Boss That Are Both Practical And Thoughtful

Shopping for your boss during the holidays can be a bit tricky. Of course, everyone’s relationship with their higher ups is different — from BFFs to terrifying supervisor — so it's good to have a wide range of gift ideas for your boss to choose from. Just make sure you’re comfortable with them opening it at the holiday party!

I’ve been lucky enough to have a lot of really great bosses over the years. Bosses who have been mentors, friends, and inspirations, and I always want to show my appreciation around the holidays. But again, your gift should reflect your specific relationship with your supervisor. If you’re close, you probably know exactly what they would like, and what they’re into. But if they’re just the person who signs your checks who you occasionally see in the break room, you might want to just get them something easy and generic. Nothing is more awkward than getting your boss a cool, customized booze bottle or a round of golf at the local range, and realizing they don’t even like those things.

When it comes to your boss, try and keep things simple — you have plenty of other people to buy for! And really, since not everyone buys individual gifts for their boss, I’m sure yours will just appreciate that you were thinking of them.

1. Desk Signs

Personality Desk Signs , $31, Amazon

Both of these signs are pretty sassy, but you can choose whichever one fits your boss' personality best. Though, they're both equally awesome.

2. Queen Bee Print

Queen Bee Poster Print , $18, E tsy

Your boss might be rocking your office environment, but they — and everyone one else — could always use a trendy reminder of their queen bee status.

3. Optimist/Pessimist Glasses

Optimist/Pessimist Glasses, $10, Amazon

I don't think the half empty versus half full personality test is better demonstrated than with these glasses. Even on a hard day, your boss can still be an optimist.

4. Starbucks Christmas Blend

Starbucks® Christmas Blend, Whole Bean, $30, Amazon

If you're not comfortable giving your boss booze for the holidays, you could always get them coffee. If you know their favorite brand or blend — perfect! And if not, grab one of Starbucks' Christmas blends for a fully festive gift.

5. Desk Storage

Office and Desk Storage Tray , $25, Etsy

This felt organizer can be used for desk storage or at your boss' home to make sure they never have to worry about where their phone or keys are, given all the regular work problems they deal with every day.

6. Planner

2017 Kate Spade New York Black Stripe Planner, $35, Amazon

A good planner is hard to come by, but this one really has it all. It's trendy, it's organized, and it's a great size to slip into a laptop bag or purse. Plus, it's hard to beat Kate Spade anything.

7. Zen Garden

Mini Zen Garden, $27, Amazon

Work can be stressful for everyone — but even more so if you're in charge. Get your boss something to help get their chill back.

8. "Thank You" Cards

Watercolor Laurel 4 Bar Thank You Notes- Set of 10 , $11, Paper Source

"Thank You" cards can go a long way — especially in business — so make sure your boss has a set of chic ones.

9. Amazing Boss Print

Typographic Art Print , $4, Etsy

Let's hope the holiday season makes us appreciate our good fortune in having good bosses. Plus, your boss' office will look chic as hell with this print in it.

10. Password Book

Open Sesame! Password Reminder Book, $11, Amazon

If your supervisor has a lot of passwords to remember, this little password reminder book will be a big help. Though I recommend making sure they keep this under lock and key, just in case.

11. Gift Basket

Snack Gift Basket- Premium , $85, Gourmet Gift Baskets

When in doubt, get your boss a gift basket. You can fill it with lots of yummy snacks and treats to help get them through the work day — they might even share!

12. Monogram Flask

Etched Glass Flask , $20, Etsy

We could all use a drink after a particularly hard day — and your boss could even sneak one with this personalized glass flask.

13. Business Card Case

Business Name Card Holder, $7, Amazon

Any professional knows that having a chic business card holder is almost as important as having a good looking business card. This card holder is leather and stainless steel, and holds up to 25 business cards (and a credit card, too).

14. Paper Clip Earrings

Silver Paper Clip Earrings, $15, Etsy

When did standard office supplies get to be so darn cute? These little paper clip studs are made from sterling silver, and bring a whole new level to your boss' business wardrobe.

15. Paper Weight

Decision Paperweight, $17, Amazon

Bosses have to make decisions all day, right? So get them a paperweight that can help then decide in a pinch.

16. Wall Print

"#BossLady" Office Print , $5, Etsy

If your boss' motto is "work hard, play hard," then this print is for them. The black and white colors and brushstroke font make it a fit for everyone.

17. Post-It Dispenser & Picture Frame

Post-It Note Holder With Frame, $8, Amazon

Post-Its are pretty standard office accessories, but that doesn't mean they have to be boring. If your boss uses a lot of little stickies, get them this awesome holder that has a space for a picture frame. It'll make them happy every time they look at it!

18. Wood Desk Set

Personalized Wood Desktop Pen Set , $16, Etsy

Personalized gifts are always a good bet when it comes to bosses. This desk set includes a monogrammed wooden desk sign and a customized wood pen.

19. Brilliant Ideas Launch Pad

Brilliant Ideas Launch Pad, $11, Amazon

I'm sure your boss has a ton of brilliant ideas just waiting to pour out — and you can help them with this cool notepad. Not only can they jot down their ideas, but the launch pad also helps them refine the ideas and put them on a path to achieving them.

20. #GirlBoss Mug

Girl Boss Mug , $13, Amazon

Your boss might be a grown-ass woman, but she's still a girl boss. I love the design on this awesome mug.