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As far as I know an adjective can be before noun(for ex. 美しい花) or before other adjective, but with て(for ex. 寂しくて眠れない夜). But in the following sentence「指定席みたいなコジンマリとした少年 」- this part is a bit of odd. Of course maybe I'm just don't know something, so can you please explain this part to me?

格好いいよりも可愛い路線で売っていきたいアイドル集団の末席が指定席みたいなコジンマリとした少年のような笑顔を向けてみた。

Thank you very much for help!

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I think you got the parsing wrong, sir! I think the sentence divides into the following:

((格好いいよりも可愛い路線で売っていきたい)(アイドル集団の末席が指定席みたいな)(コジンマリとした)少年)のような笑顔を向けてみた。

I don't feel anything wrong with 骨董品みたいなコジンマリとしたお皿, so using multiple adjectives by itself is not a problem. I think your "something is wrong" feeling is because "looks like a reserved seat" doesn't make sense as an adjective for a boy.

(I have to say the sentence is poorly written, though. Adding ',' appropriately makes the sentence a whole lot more readable!)

格好いいよりも可愛い路線で売っていきたい、アイドル集団の末席が指定席みたいなコジンマリとした少年のような笑顔を向けてみた。
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I think 格好いいよりも可愛い路線で売っていきたい modifies (アイドル集団の)末席.

(格好いいよりも可愛い路線で売っていきたい)アイドル集団の末席
the lease popular member of an idol group (who's trying to catch on by being cute rather than hot)

And I think 格好いいよりも可愛い路線で売っていきたいアイドル集団の末席が指定席みたいな and コジンマリした modify the 少年.

(("格好いいよりも可愛い路線で売っていきたい)アイドル集団の末席"が指定席みたいな)(コジンマリとした)少年...
... a quiet boy (who looks as if he's stuck in the least popular position in an idol group (who's ~~~))

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