The Duke of Windsor meets black Ivy League meets the Rat Pack meets Mean Streets

Fashionist asked this guy Chris about his fashion inspirations:

I’m really interested right now in the Duke of Windsor, just because he was so rebellious even though he was confined to this conservative background. I like the black ivy league thing that was going on with Miles Davis in the late 50s, early 60s. Also the Rat Pack, and the movie Mean Streets by Martin Scorsese.

Read on for more pics and expert analysis.

21 Responses to “The Duke of Windsor meets black Ivy League meets the Rat Pack meets Mean Streets”

  1. scum says:

    Dress shoes with no socks in the hip, wanna be euro trash look that is taking over The Mission. Smelly feet and shoes are real cool.

  2. Brillo says:

    If the Duke of Windsor wore a jacket with the sleeves 3″ too short, he would at least show off a decent wristwatch.

  3. dsds says:

    I, for one, am in full support of that hairdo

  4. Olu says:

    Forget the outliers, I see we’ve hit the tipping point, if you blink, you may miss seeing what the dog saw.

  5. Mr. Blackwell says:

    If by “rebellious” you mean “a Nazi” then yes, you’re right.

    • LibertyHiller says:

      I’m not sure which aspect of the Nazis he found more attractive: their politics or their tailoring.

  6. manymachines says:

    The last time I spent any real time without socks on was when I was five. I had grey sneakers with glow-in-the-dark Darth Vaders on the side. It was a hot look for the summer of 1982.

    Unfortunately, after a month or two of running around in them sockless, they smelled like hell. My mother initially wanted to throw them away, but after I protested she declared instead that they needed to be “quarantined” — tied up in a garbage bag and thrown in the attic for a couple months “until the smell goes away”. I outgrew them before that happened, or course.

    This is probably the origin of my borderline-pathological need to wear socks.

  7. Katie C says:

    This is so fantastic.

  8. En-Chu Lao says:

    Despite his ill-fitting jacket and Fro-fail, I’m going to come to this guy’s defense. If some of you shopped at places other than Ross, you would know that he’s wearing Italian-made no-show loafer socks; they’re about $20 a pair.

  9. En-Chu Lao says:

    Maybe it isn’t a fro, just curly big hair.

  10. Chalkman says:

    He has anice jawline