Casual/Hip shirts
I’m just wondering where the more hip style of shirts fit in. The style with the collar that is softer, a couple pockets on the front a few more sewing lines and a design on the back. The bottom of the shirt looks like it’s made be be worn untucked. Are these an immature look, is it ok to wear them as a much younger man? Are they just something you would throw on with jeans? Any input would be appreciated.

You pretty much answered all your questions already, I think: it’s a more casual style, it’s meant to be worn untucked, and it’s largely meant for young men to wear in casual settings. If you’re a young guy going out with friends, it’s fine to throw a shirt like that on with jeans. If you’re going to (or especially applying for) a job, you want something a little dressier.
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