It's no secret that picking out thoughtful gifts for friends and family members is... tricky. Even when we're shopping for the people who are closest to us, it takes a lot of thought to figure out the perfect present. Though, not gonna lie, we're pretty damn good gifters.

But if you think choosing stuff for your nearest and dearest is rough, just wait until you start browsing for your boss. You want to pick something for a superior that is classy and cool, but you don't want to get them something so over-the-top your coworkers will think you're a brownnoser. And if you get something too personal, things could get real weird real quickly.

More: 4 Effective Ways to Give Your Boss Feedback

We've got some ideas for gifts that are classic, affordable and have just enough sentiment to make your boss smile — without freaking them out.

1. Harry & David gift set

Image: Harry & David

I would typically say gift baskets aren't a great idea. But a gift set from Harry & David is classy and delicious.

Gift sets, affordably priced on Amazon

2. Personalized pencils

Image: Etsy

These could go along with the pencil holder or stand alone as a great gift.

Like a Boss pencil set, available on Amazon

 3. A pretty key chain

Image: Anthropologie

A bright, stylish key chain is something everyone can use.

Verloop tiered tassel keychain, $28 at Anthropologie

4. A cozy throw blanket

Image: West Elm

She can keep it in the office or take it home. A soft, colorful throw brightens up any space.

Coziest throw, space-dyed, $39 at West Elm

Up next: More gifts for your female boss

Originally published December 2015. Updated November 2017.

5. A funny coffee mug

Image: Etsy

For the boss with a sense of humor, this cup will hit the right note.

I Survived Another Meeting That Could Have Been an Email mug, $13 at Etsy

 6. Quality oil & vinegar

Image: Williams-Sonoma

Whether or not she likes to cook, these two items always come in handy.

Williams Sonoma House Olive Oil & Olivier 25-Year Barrel-Aged Balsamic Vinegar, $49.95 at Williams-Sonoma

 7. An amazing-smelling candle

Image: Diptyque Paris

Calming and cozy, scented candles are always a welcome gift. This soft rose one will transport her.

Roses candle, $64 at Diptyque Paris

8. Personalized luggage tags

Image: Etsy

For the boss on the go, stylish luggage tags will up her travel game.

Personalized leather luggage tags, $17.09 at Etsy

9. Wine box

Image: Artificer Woodworks

Slip a bottle of wine into this box that makes a statement. It also makes a great office decoration after the last sip.

Like a Boss wine box, $59 at Artificer Woodworks


Image: Tiffany Egbert/SheKnows