The Ugliest Style Icons Of All Time

I don’t know about you guys, but here at Four Pins, we love us some ugly. Ugly style icons are the true measure of the power of a good wardrobe and magnetic personality. I mean, if you can look like Quasimodo and still make the magic happen then, truly, there are no limits to what we can accomplish as men. And before you get all sanctimonious and start complaining about how this is a superficial sophomoric exercise in the self-serving interest of our own insecurity, just realize we are well aware of this. Four Pins ain't some handsome boy modeling school, son. We do this shit for everyone—swans and ugly ducklings alike. If these dudes can become inspiration board material, we all might just stand a chance after all—if not based solely on our stellar personalities and bench-made shoes.


  • Jerms

    Iggy Pop looks like an extra from The Walking Dead.

  • Matthew Pike

    Yuck! Wes ain’t that bad though is he?

  • KCKing

    Fucking thank you. That HBO thought they could sell us on Steve Buscemi not paying for sex is outright absurd. SAUSAGE McMuffins!

  • Vinny Tang
  • Mturman3

    George does got some mad steez. Ain’t no doubt about that.

  • Dave s

    Things that make you say hmmmmm…..

  • Jordan Tunnicliff

    Cary Grant*** Who the flip is Gary Grant?

  • Aaron

    First off Mr. Moy, I love your articles. That being said, please for the love of god stop saying “steez”.

  • Deaunte Shugart

    Rick Owens looks llike the hunch back of norte dame


  • Ho Malone

    rick owens looks like little nicky

  • Was there

    The Sex Pistols never wore “Dr. Martens and jeans”. Those would be skin-heads. Get it right.