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5 Tips for Dressing Better: Know the Rules

February 25, 2013 / by / 3 Comments

In today’s world of Crocs and fedoras, it’s not difficult to rise above the pack. Oftentimes, those who dress well stand out. But dressing well does not mean to stand out.

While there are countless aspects of sartorial style, this week we’ll discuss five suggestions that, in my opinion, are great places to start. Today’s tip:

#5: Know the rules (and when and how to break them).

“Any fool can make a rule, and any fool will mind it.” -Henry David Thoreau

Rules can be tricky. On one hand, they can be incredibly useful in preventing one from looking unkempt and unpresentable. However, rules can also be confining, antiquated codifications of past preferences. It is wise to understand guidelines and heed their warnings. It is equally wise to unceasingly question, and sometimes defy, rules –do not sell yourself into sartorial servitude.

In general, I believe that there are two basic categories of style taboo. The first category includes warnings such as:

  • -The bottom button of a suit jacket should always be left unbuttoned.
  • -A new jacket’s sleeve tags should be removed and its pockets and vents should be opened.

This category deals with how to wear clothes properly (in accordance with their intended use, that is). Bottom buttons are not designed to be buttoned, for example. Breaking these rules makes a serious statement.

The second category of rules include:

  • -Black belts go with black shoes; brown belts go with brown shoes.
  • -Button-down collars should never be worn with jackets or blazers.
  • -Tie knots should have a dimple and just reach your belt.
  • -Socks should match the color of your pants.
  • -Never wear socks with sandals.

These are much more flexible. While there may be good reasons not to deviate from many of these guidelines (e.g. black and brown usually look bad together), there are also plenty of times when breaking some of these rules can be appropriate. Matching belts with shoes and socks with pants is less important in more casual settings, for example. (We’ll discuss context later this week.)

The task for the well-dressed man is to understand the rules and the wisdom behind them. From here, he can bend them to fit the contours of his own personal style.

Breaking the rules does not mean putting on a blindfold and taking the wheel; it means coming to a red light in the dark, looking both ways, and driving on.

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C. Withorn

Chase Withorn writes "Studied Nonchalance," a segment on men's style. You can probably find him googling pictures of boots.