On Balancing Simplicity And Rakishness

August 2, 2011


I can’t find the thread right now, but many years ago, Michael Anton proposed on StyleForum that there were three stages to a man’s sartorial development. 

  • The first stage was when he becomes aware of the basic rules and slavishly adheres to them. He also goes out and gets his blue and white shirts, brown shoes, and navy jackets, as he’s been instructed to. 
  • The second stage begins when he tries to master more complex executions. He tries to pair more interesting patterns together; accessorize with pocket squares, boutonnieres, and bracelets; and maybe dandifies himself with colorful socks. The rules aren’t broken per se, but they’re stretched a little bit past the orthodoxy. 
  • The third and final stage is when he tires himself out and goes back to the basics. He’s much more at ease with his clothes and isn’t such a stickler about rules. At the same time, he understand that fit is more important than fanciful executions, so he goes back to his basic color palettes and wears well fitting things. You may see dandyish flashes at times when he wears checkered jacket here or there, but there’s nothing complicated about what he wears. This isn’t to say it’s a reversion to stage one, but rather an end point with subtleties that makes the basic look much more perfected and natural looking.  

It’s obviously a very teleological view of men’s style – a view that sees men as moving through a series of concrete stages, and always ending up at the same Zen-like end. Simple and basic, but perfectly executed. I don’t necessarily think this is the only view to have, but it’s certainly a legitimate view for some. As you move on with this, dressing well can become less novel, and thus you may find yourself going back to the basics, but in a way that’s much better executed.  

Perhaps the most interesting thing about Anton’s view is that he’s kind of a champion of conservative business dress. By conservative, I mean really conservative. He prides himself on being as boring (though still elegant) as possible. However, I don’t think his “back-to-basics” view has to be so snoozy. Tony Tanfani is a perfect example of Anton’s telos, but does it with a bit of Italian panache. Tanfani is the owner of Gisa, a boutique in Ancona, Italy. He’s always perfectly polished and incredibly sophisticated, but relies on little more than your basic solid blue dress shirts, navy blazers, and grey overcoats. In fact, he’s so pared down that he’s rarely even seen wearing a tie. It’s a style that I think can be very inspirational for people who appreciate rakishness, but also simplicity. 

An anonymous reader once asked GW what he should wear to his wedding. GW wisely suggested a navy suit and white button up shirt, to which the reader replied, “that’s too boring and easy!” He then went on to describe some absolutely ridiculous outfit he was planning to wear. I think it was something like a burgundy plaid suit with an ancient madder tie and a tattersall shirt. There was something sophomoric about the reader. He seemed like a man in Anton’s second stage.