the plaid shirt is seen in season 6, episode "no more drama" and its the morning after the break in. if you google "entourage no more drama" you can see the shirt under images.i must find this shirt!
here's the shirt!
http://www.google.com/imgres?imgurl=http://i.cdn.hbo.com/assets/images/series/entourage/episodes/6/73/no-more-drama-05-1024.jpg&imgrefurl=http://www.hbo.com/entourage/episodes/6/73-no-more-drama/slideshow.html&usg=__EGWItG7-OFSuHonMJNNytCY9ROw=&h=576&w=1024&sz=220&hl=en&start=20&zoom=0&tbnid=L0CuJfKg9BKG1M:&tbnh=84&tbnw=150&ei=NVZ4TemGH8qdgQfD_vjTBQ&prev=/images%3Fq%3Dentourage%2Bno%2Bmore%2Bdrama%26um%3D1%26hl%3Den%26sa%3DN%26biw%3D1161%26bih%3D763%26tbs%3Disch:10,659&um=1&itbs=1&iact=rc&dur=398&oei=k1V4TY-YIcSBgAf19Oy3BQ&page=2&ndsp=24&ved=1t:429,r:8,s:20&tx=43&ty=49&biw=1161&bih=763
here's the shirt!
http://www.google.com/imgres?imgurl=http://i.cdn.hbo.com/assets/images/series/entourage/episodes/6/73/no-more-drama-05-1024.jpg&imgrefurl=http://www.hbo.com/entourage/episodes/6/73-no-more-drama/slideshow.html&usg=__EGWItG7-OFSuHonMJNNytCY9ROw=&h=576&w=1024&sz=220&hl=en&start=20&zoom=0&tbnid=L0CuJfKg9BKG1M:&tbnh=84&tbnw=150&ei=NVZ4TemGH8qdgQfD_vjTBQ&prev=/images%3Fq%3Dentourage%2Bno%2Bmore%2Bdrama%26um%3D1%26hl%3Den%26sa%3DN%26biw%3D1161%26bih%3D763%26tbs%3Disch:10,659&um=1&itbs=1&iact=rc&dur=398&oei=k1V4TY-YIcSBgAf19Oy3BQ&page=2&ndsp=24&ved=1t:429,r:8,s:20&tx=43&ty=49&biw=1161&bih=763