YOU SAID:
Steve walks wearily down the street with the brim pulled way down low.
INTO JAPANESE
スティーブはつばを低く引っ張って通りをうんざりして歩く。
BACK INTO ENGLISH
Steve pulls his collar low and walks fed up on the street.
INTO JAPANESE
スティーブは首輪を低く引っ張り、通りでうんざりした。
BACK INTO ENGLISH
Steve pulled his collar low and got sick of it on the street.
INTO JAPANESE
スティーブは首輪を低く引っ張って、路上でうんざりした。
BACK INTO ENGLISH
Steve pulled his collar low and got sick of it on the street.
That didn't even make that much sense in English.