I think I would have to say that my all time favorite supply has been my recollections desktop carousel that sits proudly in the center of our desks! That thing gets used daily, ad it helps stabilize my desk setup.
What’s your favorite can’t live without supply?
We have the same caddy and love it. I did find the twist up crayons and sometimes pens would lean to the side too much and be difficult to get and put more back. My kids like to take all the colors they want to use out at once and then put them back. I found that by putting a few toilet paper holders and cutting them to fit it solved that issue. Now they stay upright even when a bunch are pulled out. It took me 2 yrs of having the thing but I recently moved the kid scissors to where the elastic is. I think yours is a different model. Mine has elastic and hooks and a pocket for a pic on 3 of the sides where yours has the label holders. I had no idea how to use the elastic until just recently. It’s been working great.
My favorite are small dry erase boards with paper lines from the dollar store. They are perfect for practicing writing for my kindergarteners and first grader without creating mountains of paper work. It also has upper and lower case letters across the top and bottom with arrows showing jow they are written. Which was perfect for tracing when they were younger and is a good reminder that they can look to when they forget which way a lower case d or b faces. They also have an empty back that we write on for other things that don’t need lines like math. You can’t beat all that for a dollar!
Mine is my laminator. I’m laminating crazy. But I love your caddy. I really need to get one like that. I just love it!
I Love Love my HUGE roll of butcher paper…you can rip off a piece and use it for art, quick scratch paper, even a last minute happy birthday sign!
A timer! My son loves it. He uses it for speed drills, copywork, and reading time. He is very motivated when he knows exactly how much time he will be doing something.
I love highlighters and pens. I like to highlight to differentiate papers and each subject has it’s own color. School supplies are my kryptonite
I too love my caddy! I found mine at Hobby Lobby and was able to use a 40% coupon. The drawer have magnets at the back to keep them from falling out. Everything fits in the caddy! Even rulers! Love it!
My three hole punch! 
Any my mini dry erase board…which has doodle marks all over it from the past 8 years. Makes me happy.
Small dry erase boards work great for us. When I don’t want to waste a piece of paper or go to the big white board, these are perfect for rewriting a math problem, spelling test for my 8 yr. old, or diagramming a sentence.
I love our Crayola Dry Erase Activity Center boards. I have one for each kid. It makes me feel like I’m not wasting ink and paper because I can just slide printables in them then they can do the work with a dry or wet erase marker and the we wipe it clean when they are done. Then the printables are still in perfect shape and I can store them for next time or use them for another kid.
My old time large office paper cutter! Not a fan of using scissors…
Oh my goodness! I have so many of them! I LOVE getting new pens, pencils, and notebooks! Back to school shopping(for supplies) is one of my favorite times of year! I make lists of everything throughout the day so I love having pretty paper to write them on. (My 9 year old daughter is taking after me with writing lists!) I do have a caddy but it’s the Pampered Chef utensil caddy. I use it for pens, pencils, erasers, markers, scissors, glue sticks,etc. My printer, which I use ALOT, is also a favorite!
We use a laminated world map all the time during bible and prayer time. It takes a beating and then we just roll it up until the next time we get it out.
My all time favorite school supply would be crayons, binders and file folders. Crayons because I also love to color, alone or together with my daughter; binders, to keep every artwork and worksheets organized and together; and file folders for lapbooking. Would love to have a recollections desktop carousel though, so all the crayons, pens, pencils and markers are contained in one neat place. 
I just bought a binding machine. Totally not necessary, but I love it. I’m thinking of all kinds of ways to use it. I just bought this little gem http://store.notconsumed.com/breakfaststation/ and this little gem http://store.notconsumed.com/2014/09/22/lunch-station/. Sure I could have put it in a bulky binder, but space is a premium here so now I have 3 cute little binded packs to make meals a little less crazy. I also love my laminator http://www.amazon.com/Scotch-Thermal-Laminator-Roller-TL901/dp/B0010JEJPC/ref=sr_1_1?ie=UTF8&qid=1424938329&sr=8-1&keywords=laminator. I used it to make a sturdier cover for my breakfast and lunch station binded packs.
rings, I love them because I make lots of flashcards!
I love buying pencils and binders. Actually any school supply.
I would say highlighters. I highlight problems we need to do, words to read, lessons accomplished. I use different colors for different days as well.
We use a lot of copy paper. I use it to print printables from my iPhone, draw story webs, create mini books (fold 4-5 ages in half and staple), drawing, painting, and so much more. We recycle some papers by using the opposite side for math notes, studying spelling and doodling. Today, our 3 year old daughter was ripping up copy paper to make a play ground for a cricket she found and thinks is her pet. 