“Being in the box” – have we made the “box” into a coffin? Is “the derech” too narrow?

What’s the definition of being on the “derech” and “in-the-box”?
How have those definitions changed over time?
Is the “derech” too narrow and the “box” too confining?
Does being “out-of-the box” violate Halacha or just societal expectations and norms?
Are there halachic requirements to: wear white shirts and black pants, always wear a hat, go into certain occupations, not play sports and music?