What year did baggy clothes go out of style? Because on Swagga like us Jay Z says I cant wear skinny Jean's my Nots dont fit, that song came out in the fall of 2008. I wasstarting my freshman year of college and people in my age group for the most part were still wearing baggy Jean's. I didn't even realize how popular skinny Jean's were until one of my friends asked on Facebook" What's up with these high school kids walking around wearing their little ten year old sister's clothes, this was around 2010.