While reading the fashion focused Time Magazine supplement I spotted a men’s Skechers ad featuring the normally sexy man hunk that is Jake Gyllenhaal. Normally Jake can do no wrong!  In this ad, shot in 2006 for Sketchers, Jake appears to be 17 or fresh off the Bubble Boy set! If anything he needs to fire his print agent for not discussing usage rights. Who agrees to 2+ years print campaign?!

Now the ad wouldn’t be half as bad if it didn’t appear to be so poorly Photoshopped. What is with random Concubine who obviously got dressed in the dark in the back?

No matter how tacky and old this ad is, we can agree with it on one level…

Jake Gyllenhaal, we love you long time…

The fall 2008 Boss Orange Collection aims to evoke the spirit of irreverent, individualistic and authentic individuals. The collection intention is to wear from day to evening for a variety of occasions.

In my expert opinion as a consumer, shopper and fashionista the only message in these sloppy ads is “Hot Mess Coming at Ya!”

The sweater… or Poncho… (Maybe Swoncho??) is more reminiscent of my grandma’s 70′s shag carpet!

The pants prove that wrinkles and the creases can coexist in the same space and lead me to believe that the fit is closer to that of Lee Dungarees rather than classic Boss.

The mismatched careless alignment on the striped shirt just screams discount dime store!

This look was more likely inspired by Sesame Street’s Snuffleupagus than Johnny Depp and singer Vanessa Paradis!

Snuffleupagus, could not be reached for comment.