Walmart is as about as cool as Michaels and TJ Max when it comes to retail but the king of the hill is trying desperately to reinvent itself through strategic online acquisitions.
Most notably, Walmart scooped up eCommerce retailer Jet.com that will help them compete with Amazon for quick and easy online purchasing in all categories. In the clothing category they acquired Bonobos who has a killer brand and really expensive chinos.
This doesn't make Walmart cool.
How can they be cool?
Take a page out of Google's playbook. I recommend Walmart create a parent company like Google did with Alphabet. Walmart's version of Alphabet can be the cool parent and have some cool kids and yeah, Walmart can be the fat old kid who is their favorite too. I know Walmart is doing a ton of investment in AI/big data/(anything transformative) but I just don't see how the really cool kids in the valley would want to move to Bentonville, AR to be a dev at Walmart. If there was a parent company focused on development based in the valley or Austin, they might have a shot at being.... cool.
