My super skinny 6 year old has used a spibelt with some success, a little more with an actual messenger bag modeled after dad's get ready for work routine. I so feel you on boys carrying meds.

My 6yo son has had great success self carrying in kindergarten. We use the XS onespot allergy belt and he carries one epi (that's all his tiny frame will allow). The belts have begun to wear through on the areas where the ends of the pen are. I used to rotate belts, but we're now down to only one, so not sure how long it will last. I love these belts b/c they are tiny and very discrete. Unless you know he's got it on (which his teacher and classmates do), don't even notice it.

Any suggestions for something similar? How I wish boys carried adorable little purses too