This student is always wearing clothes that are wrinkled and the fabric around his neck looks stretched.
ご質問ありがとうございます。
・「This student is always wearing clothes that are wrinkled and the fabric around his neck looks stretched.」
（意味)ある学生はシワのよった服を着ていて首の周りの布が伸びています。
<例文>This student is always wearing clothes that are wrinkled and the fabric around his neck looks stretched. I think he needs new clothes.
<訳>ある学生はシワのよった服を着ていて首の周りの布が伸びています。 新しい服を買わないといけないと思います。
参考になれば幸いです。
His clothes aren't stylishly disheveled; they're just sloppy and worn out.
His clothes aren't stylishly disheveled; they're just sloppy and worn out.
It's not an effortless look; his clothes are just wrinkled and stretched out.
・stylishly disheveled
disheveled は「（髪や服が）乱れた」という意味ですが、前に stylishly をつけることで、計算された「おしゃれな着崩し」を表現できます。最近では effortless（努力を感じさせない＝さりげなくおしゃれ）という言葉もよく使われます。
アメリカ合衆国 
