It's often used to describe someone who is enjoying a privileged or effortless lifestyle.
Here are some examples of how it might be used:
* "Ever since she inherited that money, she's been living made in the shade."
* "He landed that dream job with no experience? Must be made in the shade."
* "I'd love to be made in the shade like you, just chilling out all day."
The origin of the phrase likely comes from the idea that people in the shade are protected from the sun and heat, making them more comfortable than those exposed to the elements.