20 Pieces of Clothing Every Teacher Needs in October

2 min


Getting to dress in crazy, cute, seasonal attire is one of the many perks of being a teacher. Throw on one of the below items and get ready to be complimented all month long by your students!

Just so you know, Bored Teachers may get a small share of the sales made through the affiliate links on this page.

1. A super soft tee that gives a nod to Maleficent

Get it HERE.

Do you teach elementary students? They’ll get a kick out of this shirt, which quotes the ever-popular Disney movie, “The Descendants”. 

2. A peter-pan collared dress

Get it HERE.

This look is very “Wednesday Adams”. Feel free to leave it as is or use it for one of the many costume parties you will be sure to attend. 

3. Luxuriously comfy leggings

Verabella Women's Skull Pumpkin Ankle Length Stretchy Legging Pants

Get it HERE.

Throw a tunic over these Halloween leggings to show off your holiday spirit! 

4. A Hocus Pocus shirt

Get it HERE.

Your students will get a kick out of this shirt featuring the Sanderson sisters in all of their glory. 

5. A sweatshirt you should probably save for the weekend.

Get it HERE.

As a teacher, we’re always here for the “boos”, so this is VERY on brand. 

6. A super simple baseball tee you can wear all month long. 

Get it HERE.

This cozy long-sleeve transitions perfectly from crisp autumn breezes to cooler, stormy nights. 

7. A classy skirt with a variety of Halloween prints to choose from.

Get it HERE.

This skirt screams polished and professional! Plus, there are so many fun designs to choose from. You can even buy a Christmas skirt while you’re at it!

8. A Winnie Sanderson classic. 

Get it HERE.

Instead of repeating yourself, just point to this shirt to make sure your students are understanding the words that are coming out of your mouth. 

9. A cute Disney tee that your littles will love!

Get it HERE.

Don’t want anything too scary for your younger students? This tee is perfect for getting in the Halloween spirit without scaring anyone away.

10. A conservative dress with a pattern to die for!

Get it HERE.

Choose from skeletons, pumpkins, ghosts, bats, and so much more. The design options are endless with this dress!

11. A tee celebrating your love for “Stranger Things”. 

Get it HERE

Teaching sometimes feels like you are “stuck in the Upside Down”, am I right? 

12. A sweatshirt to really bring out your inner cat lady.  

Get it HERE.

This adorable sweatshirt will keep you nice and toasty on casual Fridays.

13. A long cardigan to layer over one of the many cute tees on this list. 

Get it HERE.

The skulls on this cardigan represent teachers’ souls this time of year – absolutely lifeless with the ability to sleep for all of eternity. 

14. A shirt to release your inner witch.

Get it HERE.

For when you feel like flying out of staff meeting and into the abyss of the night. 

15. A “Basic Witch” shirt.

Get it HERE.

Wear this as you sip your venti Cold Brew and bask in your basicness. 

16. A shirt celebrating your love for your students.

Get it HERE.

17. Slimming black leggings. 

Get it HERE.

Loud prints not your thing? These subtle leggings are for you! They show that you are in the holiday spirit without being in your face obnoxious about it. 

18. A loose shirt you can wear beyond October.

Get it HERE.

This shirt is non-form fitting and perfect for when you eat loads of candy. 

19. A shirt that says what all teachers are thinking.

Get it HERE.

Why did we all choose a profession that makes you get up at the crack of dawn?

20. A shirt for all of the pregnant teachers out there.

Get it HERE.

Wear this shirt and be sure to get all the tiny hands on your pregnant belly at once. You’ve been warned!


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Abigail Courter is a fifth year music teacher at a K-8 private school in California.  She has taught general music, band, music technology, and performing arts.

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