40 Halloween Costume Ideas Perfect for Teachers or Family

Want some easy, funny, creative and affordable costume ideas?

I’m thrilled to welcome my friend Jess Samuels to divulge how she was able to pump out dozens of costume changes over the years — while spending very little money. Jess will intersperse her Halloween knowledge with tidbits about what it’s like to work at an EdTech company.

Teaching Traveling: Welcome, Jess! Tell us a bit about your background.

Jess: Hello! I have a long career in Student Affairs, having started working and living in a Residential Community as an RA back in undergrad. Eventually I found myself as a Director of Residence Life (teaching Introduction to University classes to first years). 

For the last 2.5 years, I transitioned over into the EdTech space at an education technology company called 2U. I was working in student support for a Coding and Data bootcamp, then as a Program Manager, and now Product Evangelist (jobs change quickly in EdTech).

While I don’t get to travel much, especially during the events of 2020-21, I do get to work with people all over the world. 2U has 11 offices, including in London, and Cape Town. While I have yet to even visit the headquarters in Lanham, MD, maybe one day I will get to meet one of my many co-workers across the world!

TT: How does an EdTech company that has offices and employees all over the world keep people connected?

J: I think that 2U does a great job at seeing the value in human interaction, especially when everyone is online.  Regardless of whether someone works in one of the 2U offices, they might have meetings with team members across time zones, or connect with someone from another state/country in one of the many social or professional development opportunities offered weekly.

I am a part of a Business Resource Network (BRN) – which is basically like an Affinity Organization from college, but for adults.  2U has several BRNs, BNet (Black Network), W.A.N. (Womxn Action Network), 2Q (LGBTQIA+ Network), TuGente (Latinx Network), APIN (Asian Pacific Islander Network), and ARN (Ability Resource Network), all of which are responsible for ongoing programming that allows us to connect with other 2Utes. 

As the Global Chair, I am ecstatic to have two members of my executive board working out of Cape Town.  While it doesn’t make scheduling meetings easy, it means that we have folks on our board offering an entirely different, non-U.S. centric perspective on every event we run, or article we post.

TT: Are there any special events that 2U is known for?

J: Internally, all 2U employees know that Halloween is a REALLY BIG DEAL. Our CEO Chip Paucek is a huge fan, and has always hosted Halloween parties at the company offices. 

Since I have always been remote, I was delighted when all of the Halloween activities were brought online — and we had an entire week of 2UBoo to celebrate — with activities planned such as trivia hours, escape rooms, video contests, pumpkin carving contests, and my favorite, the costume contest.

TT: How did you celebrate 2UBoo?

In my first year of the online 2UBoo, I decided, on a whim, to show up in costume for the first meeting of the day that week. It was just a simple Where’s Waldo Costume we had hanging around the house. 

My co-workers got a kick out of it, and I had another meeting with most them later in the day and thought it would be funny to show up in a different costume. I quickly dug a plaid shirt out of the closet and paired it with a Cowboy hat. 

Next thing I know, I started making plans for changing my costume once every meeting for the week. That first year I ended up doing 19 costume changes (see the photos here), including the much celebrated doppelganger of my Boss (who’d been there for only 1 month!). I took home one of the “Most Creative” costume contest prizes for my version of Ruth Vader Ginsberg (no, that is not a typo).

For 2021 I knew I had to step up my game.  I took some time the weekend before to plot out all of the costume changes on a spreadsheet, assigning a theme to every day. I knew that the costume was really only 30% of the show, and having the right background was key. 

I spent hours each night downloading backgrounds and laying out my costumes so I could manage 5 min (or less) costume changes between meetings. In 2021, I took home the top prize for Most Funny costume, and 2nd prize overall by imitating our CEO Chip Paucek.

I was also inspired by the Bus Brothers, and decided to pick up my oldest from the bus in a new costume every day. It was a lot of fun to surprise my kiddo (and his bus mates) as I showed up in everything from a Chewbacca to a Maleficent costume.

TT: Wow! Did you purchase your own costumes?  How do you make this affordable?

J: 99% of my costumes were acquired for free.  In many cases (Finn, Iron Man, Spiderman), they are actually just kids costumes binder-clipped to my shirt, and with smaller masks I hide my chin with a balaclava.  Online video calls allow you to get away with a lot you couldn’t if you were walking into an in person office.

I started my costume collection when we ran a kid’s clothing swap group back in Boston gathering 100-150 people per swap, every month for almost 4 years. Post Halloween, Costumes would be dumped off in mass, and we started holding them until the following Halloween. Also, occasionally my Buy Nothing neighbors would be getting rid of costumes and I would always jump on the chance to gather more (see below).  

Since I moved to a new town north of Philly, I put a call out to neighbors, and I ended up borrowing eight of my costumes this year.  It’s pretty easy to do things cheaply when you use your extended network.  People love to help and they love to see the final results.

TT: What advice do you have for educators who are working in an online space?

Have fun with it.  Have costume days, change your background, dye your hair, have ice breaker questions in staff meetings (I do this every week!). The monotony of being on your computer day in and day out is tough, and so anything you can do to bring joy for yourself and your students is worthwhile.  Competitions and team games always get people in a different frame of mind and may shake things up.  

Connect with others as much as possible. Yes, you may be tired of being online by the time the school day is over. But online connections with people doing the same lesson planning as you, or people who you just enjoy (online book clubs are big) can be a life saver for staying connected to other human beings.

TT: Thanks so much for these Halloween costume ideas, Jess! Readers, what questions or comments do you have?