New Rule: Rule 49

New Rule: Rule 49


49.  Never, ever, ever wear a black dress shirt with a suit (or a dinner jacket/tuxedo for that matter).  Just because they may be or may have been ‘on trend’ does not mean one will ever look good on you.


PS – I have nightmares about things like Matt Damon’s ensemble above.  You may think I’m joking, but sadly, I’m not.


  1. While agree with you on black on black, you are completely against black shirts and that frankly does not make sense to me.

    • Tony,
      I am against black shirts with a suit or a tuxedo. Although I really don’t like them worn without a jacket, I am not completely against them (although I never wear them).

  2. I disagree. If the shirt has a nice cut as well as the suit it can have a very good neutral effect making the wearer standout as opposed to the clothing. I personally rarely wear black shirts because I fear looking like a hired hand/security person but can see the appeal to some in the sense of uniformity. I stress that the cut of both shirt and suit should be sharp enough that it bridges formal and casual