Rebel Style: Which Style Rules Do You Routinely Break?

September 8, 2016

Rebel Style: Which Style Rules Do You Routinely Break?

“You have to learn the rules before you can break them” is the kind of wisdom imparted by people who don’t really want you to break the rules. The Bruce Boyer piece Derek talked about yesterday is technically a list of commandments, but none of those rules is truly prescriptive, like “Never button the bottom button of a suit,” or “Don’t buy a black suit.” Now some of those rules are too basic to make the cut on a meaningful list from Boyer. The truth is that few rules are absolute and all of them change over time, and dressing well in the long term is a matter of sticking to your principles but being flexible on the details.

Last weekend I taught a couple of classes on men’s style at Maxfuncon east that addressed some basic ground rules that are virtually indisputable. The ultra seriousness of the discussion was not at all undercut by the setting.


Photo credit: Erik Westra

The attendees were universally handsome. We talked about rules, trends, heirlooms, awesome thrift finds, and the perfect wardrobe design for Bill Lumbergh. A recurring theme was rules that are broken, sometimes because we don’t know the rules, sometimes because we don’t care, and sometimes because we know and feel like breaking them anyway.

  • I sometimes wear oxford shoes casually, and derbys with more formal suits. (Even so, I felt like i needed a caveat here to say not, like, with formalwear–just to preserve a shred of credibility.)
  • Several class attendees felt the same, and appreciated the sleekness of a derby even with denim.
  • One of the attendees likes wearing a pair of vintage tux pants, satin stripe and all, casually.
  • I wear OCBDs with suits fairly often. I think they look pretty good.
  • So long as my belt and shoes are in the same general color family—black with black—I don’t really care how close a match they are.
  • In winter I wear pretty formal overcoats with pretty much anything.
  • I own and wear flip flops and other toe-baring sandal-y footwear.
  • Likewise I wear brass belt buckles with a silver-toned watch and ring.

What menswear rules do you happily break?