So after a lack of great options given I went searching for a better cooler option. I found two that I’m very happy with. Both on amazon prime; both less than $16.

On the left is an insulated soft cooler by Mier. I can easily fit 6 full size shakers upright in it without cramming. I also was able to fit 5 standard height Rubbermaid Takealongs and two shakers. Both options had room for some ice packs. There large mesh pockets on either side large enough for a 40oz hydro flask, a zippered front pocket, and an internal lid flat pocket. This seems ideal for a quick trip or couples day away. 6 Shaker Cooler

On the Right is a smaller insulated soft cooler by Amersun. It easily holds two full-size shakers upright with room to spare. A third shaker was a bit too much for it, however clearly enough room for a ice pack and small snack. Designed to be kept upright, it does not easily tip when fully loaded and slips nicely into my backpack for walking. It also has a sling strap for carrying 2 shaker cooler