What will I wear? It seems like a simple question and, to an extent, it is. However, the clothes we choose and wear out into the world are part of the masks and costumes that represent who we are on the inside, or at least, they should be.

In the world of fashion women are given carte blanche to experiment and embrace trends as they’re presented at the fall and spring fashion shows. Men are encouraged to be prudent in embracing styles, at least adult men are.

As teenagers, boys have their choice of costume to use to declare what they are into. From aligning with bands like Death Cab for Cutie with jean skinny styles or blasting Jay-Z with oversized jeans strapped underneath their buts with belts. Extreme? Sure, but also part of the teenage experience. Outside of being a performer, it becomes more difficult for adult men to carve out their identities in an understated way.

Using the past to influence the present is the best way for men to carve out their sartorial identity in a fashionable way without the calculation inherent in many outfits. There are timeless pieces to include in any mans closet from crisp dress shirts and slacks to jeans. Across time periods, the underlying component to making clothes timeless is their fit. Tailoring and knowing the proportions of your own body is the most important part of finding the right clothing.

Using classic pieces as dogma in outfit construction isn’t the way to go about solidifying a sense of style. Looking at men’s style icons for inspiration can act as a template to discovering your own self. The leather brown boots of actor Steve McQueen, the black turtlenecks of musician Bob Dylan, even the iconic eyeglass frames of film maker Woody Allen identify them.

Trying to keep up with the times is anathema to being truly stylish- attitude coupled with clothing that is so neat as to be almost invisible is what separates men from boys and is incredibly seductive to women.

The fashion upside for men is an insistence on simplicity. Accessories are sparse at best from a knotted scarf, to a streamlined men’s sport watch, to a wedding ring. Finding the silhouette that works for your body shape without straining to make your shape work for the clothing is a fashion rule that crossed both genders. Clothes do make the man if they are picked with simplicity and elegance.

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