Even though you might think some clothes look cute, they often don't look that good on you.
ーEven though you might think some clothes look cute, they often don't look that good on you.
「洋服を可愛いと思っても、その服が似合わないことがよくある」
to look cute で「可愛く見える」
often で「よく・しばしば」
don't look that good on ... で「…に似合わない」
ご参考まで!
・Things that look cute don’t always suit you when you wear them.
・Things that look cute don’t always suit you when you wear them.
見て可愛いと思ったものでも、着ると似合わないことはよくある。
→ don’t always を使うことで「よくある」というニュアンスを自然に出せます。
・Clothes can look cute, but not look good on you when you try them on.
可愛く見える服でも、着てみると似合わないことがある。
→ try them on を使うと「試着してみる」という意味です。