Zero chance this kid knows how to tie a tie but I guess you gotta start somewhere.

Time to reload the Miltons machine. Send all sob stories to pimpmylook@barstoolsports.com or pimpmydate@barstoolsports.com and help us help you. And you need to send pictures! If you sent an email without a picture resend with one to be considered.

Today’s Contestant


Reader Email

El Pres,
I’ve never been a huge fan of this website (no offense), but my friends and I are reaching out to you because our buddy needs your help. He’s a cool guy, but due to the way he dresses its sometimes frustrating to go in public with him (especially when chasing tail). He wears clothes that he thinks people will find funny, as opposed to wearing clothes in order to look appealing. Everything said and done, we need him to stop dressing like a moron.

Best,

His unfortunate friends