Posted in Teaching Life

The Perfect Itinerant Teacher Bag: So Much Searching

I have had many, many teaching bags over the years. With each purchase there is a hope and a dream that this will be “the one”. I get excited when I think I have found it…the bag that will end all bags, but sadly I keep searching….and spending.

Is it me? Is it the bag? Is it a bag addiction?

Messenger Bag

Almost looks new

This was the first style of bag I started with. I loved it in college, so I bought a new one when I started my itinerant position. I wanted to look put together and not like a student. It was not a good choice. It could not hold enough. Depending on my caseload I might need bigger items and this was definitely the case years ago, so then I was carrying two bags! Who likes that?! I know some itinerants have to and I get the two bag need, but I needed to carry smarter. I had to kill this messenger!


  • Light weight
  • Wipes clean
  • I hoard and carry less
  • Pockets for organization
  • I look professional


  • Not enough room to do my job

Tote Bag

Vera Bradley, thirty-one, Lug

I probably have the most of this style. I was going to take a whole group photo, but I think that might be incredibly embarrassing and make me cry over the dollars spent in pursuit of happiness. I have some really cute ones and I will go back to them to spice up my day to day momsibilities or carry extra stuff when needed, but a couple of these haven’t seen my back seat or a school in years.


  • Depending on size- holds a lot
  • I really like ones with outer pockets
  • Some are machine washable
  • Durable
  • I look like a teacher…not a student


  • Some are and endless pit
  • I load them to heavy
  • Open tops- rain or snow
  • Shoulder pain

Rolling Bag

Amazon special

I know this style of bag is used by so many itinerant teachers. We have a lot of stuff sometimes and carrying the world on your back hurts, so why not roll it behind you. I tried this bag. It has pros and cons for me. I have a nickname for the rollie-The Rolling Bag of Shame. I am very aware that this is not a cute one or high end version, but it has wheels and that was my experiment. After a good, solid try it rolled right down to the basement.


  • I am not carrying the world on my back
  • I can fit a lot in it
  • I can move about quickly


  • Loud-I am so noticeable
  • Gross in the snow
  • Stairs are difficult, so I have to carry
  • Lifting it into the car
  • Zero organization- it is like a pit


Never going to have a sensible black bag

This is my latest bag I am using, even though I told myself I would never get a backpack. I was totally against looking like my students.

As I have worked as itinerant for over a decade I have thankfully made friends. With these connections I have been able to leave things at my different schools. This has made life considerably easier, so my need for a huge bag has decreased.

This past school year I was using a large tote with zero issue until I was off balance on some ice this winter. I prefer to travel and work without crutches, so I decided to cave and get a backpack. I went to Vera Bradley and found a pattern that I thought would be cute all year and hide dirt-it goes on the floor beside me a lot.

So far so good.

Getting older sometimes means doing things for safety and health, so backpack it is!


  • It is a fun pattern
  • Light weight when empty
  • Easy to carry
  • Pockets and organization are plentiful
  • Washable
  • I can maneuver quickly
  • Adjustable over winter coats


  • I get mistaken for a student….from behind
  • I load it heavy at times-ouch

So far this is the winner. Never say NEVER.

Also, I can purchase matching accessories for this particular backpack. I love that…of course!

The search is over….for now. If I end up finding “the one”, yet again, I will update this post or add it to my Buffet page.

If your a professional bag lady like me drop me a line. I would love to know what works for you!!!


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