YOU SAID:

Ian wears his white socks up very high, it looks very silly

INTO JAPANESE

イアンは白い靴下を非常に高く履きます。

BACK INTO ENGLISH

Ian wears white socks very high.

INTO JAPANESE

イアンは非常に高い白い靴下を履いています。

BACK INTO ENGLISH

Ian is wearing very high white socks.

INTO JAPANESE

イアンは非常に高い白い靴下を着ています。

BACK INTO ENGLISH

Ian is wearing very tall white socks.

INTO JAPANESE

イアンは非常に背の高い白い靴下を着ています。

BACK INTO ENGLISH

Ian is wearing very tall white socks.