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Breaking Fashion Rules

Most men need hard-and-fast facts to keep their style selections in check. Pleated pants? Nope. A chambray shirt with jeans? Try again. The truth is, though, rules were meant to be bent. So consider this list your (almost) unbridled permission to be perverse. Here’s how to break the fashion rules.

RULE: Never wear shorts with a sportcoat or bucks
You can actually wear shorts with a sportcoat and bucks. The key is to make sure that both the shorts and sportcoat are impeccably tailored. Think more Bermuda inhabitant than overgrown schoolboy. But please, skip the knee highs — no socks necessary here.

RULE: Make sure your pants cover your ankles
A hem that hits above the heel sounds about right if you’re headed to a boardroom or a Bar Mitzvah. For the other 90% of your life, feel free to relax and roll up your khakis and jeans. An inch to an inch-and-a-half should do the trick. Ankles can be bare, but showing a smidgen of sock — preferably with a pop of color — is a nice touch, too. If you look like you’re ready for a 40-year flood or a circus, you’ve likely gone too far.

RULE: Avoid clashing black with navy or brown
Old-timers will tell you that navy suits should never be paired with black belts and shoes. There’s an even harder style stance when it comes to wearing black and brown. But as the saying goes, black really does go with almost anything. Here’s how to break the fashion rules for navy or brown with black. Make sure your brown bluchers are polished to perfection to match the inherent sleekness of their darker background. Another tip here is to use different skins and fabrics. For example, a pair of black leather driving gloves will work well with a brown wool overcoat.

RULE: Always match your shoes and belt
This fashion rule probably came from a long line of color-blind gents who couldn’t discern the difference between black and brown. But if you’re blessed with the color-recognition capability of a kindergartner, focus your efforts on color coordination rather than cloning. Brown shoes, for example, should certainly partner with a belt of a similar tone (one that’s too light or of the cordovan camp would be needlessly distracting). By the same token, if you’re daring enough to sport drivers in, say, a rich, red suede, let the shoes do their job and let a more neutral belt take the backseat.

RULE: Steer clear of pleats
Indeed, even we’re guilty of helping etch this dress dictum in stone. The real problem, however, isn’t with the pleats. It’s with the pants themselves. The mass appeal of ’90s-era pantaloons (thanks in no small part to MC Hammer and an Italian designer that shall remain nameless), with their wide legs and shapeless silhouette, gave pleats a bad name. Our take: As long as there isn’t an army of them and the legs are properly sized, you’re on the path to pleated perfection.

RULE: Stay away from denim on denim
Doubling down in the denim department is a dangerous road to travel. A slight turn in the wrong direction could land you with an agricultural aesthetic you weren’t exactly going for. Can you break the fashion rules by wearing jeans on jeans? Yes. Sync tonalities and patinas — dark with dark and washed with washed — but never match them exactly. In the end, you may just pull this one off.

RULE: Limit your pick of patterns
After spending countless Sunday nights circa 2000 watching a solid-on-solid-on-solid obsessed Regis on Who Wants To Be A Millionaire?, it’s safe to say we were all ready for a plaid or a pindot. Over a decade later, though, there’s still some lingering trepidation. Matching and mixing patterns is really just a simple game of color and scale. The strategy for winning results: Coordinate the former and contrast the latter. A blue gingham shirt with a blue and orange rep-stripe tie under the subtlety of a navy windowpane jacket, for example, should pay off handsomely.

The law of the land always rules supreme, and fashion is no exception. But remember: It’s through interpretation, not total violation, that a personal sense of style is born.