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を着よう

shall I wear

→ を
phrase Rare #39,157
shall I wear The volitional form of 着る, used when deciding or wondering what to wear. Depending on context, it can also mean “I’ll wear.”
JA: 今日はどのジャケットを着よう？
EN: Which jacket shall I wear today?

別の服を着よう、別の靴で。

Let's put on different clothes and different shoes.

今夜は何を着ようかしら

I wonder what I should wear tonight.

— ミッション・クレオパトラ (2002)

セーターの上に何を着ようかな？

What should I wear over my sweater?

今日はこの赤いセーターを着ようかと思っている。

I think I’ll wear this red sweater today.