Dan Levy: The Good, The Bad & The Trendy

Confidence is key to Dan Levy's personal style

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Photo by Justin Broadbent

There was a time in my life when people called me “Denim Dan.” I didn’t like it. And fortunately for my self-esteem, it didn’t stick for very long. I was 12 and I was given the name by my classmates after I showed up to the first day of school in—wait for it—triple denim. It was an aesthetically challenged outfit consisting of what I can only now imagine to be viciously unflattering front-pleated jeans, an equally uncompromising blue chambray button-down shirt and a denim jacket. It was the height of Gap’s big denim craze and crazed I was.

On the upside, Denim Dan scared me into never following a trend from head to toe ever again.

A close friend of mine who works in fashion once told me that when it comes to life, love and the way you dress, “wear it like a loose garment.” The implication being that you should always try to be comfortable, casual and cool in every decision you make.

Ironically, fashion trends, be it denim or polka dots, have a tendency to perpetuate the contrary. Following a trend too closely is a risky thing. If not properly executed, you could easily end up looking uncomfortable, over-styled and downright foolish. Trust Denim Dan on this one.

It’s an amusing thought, this idea that it’s been ingrained in us to be leaders and not followers, to avoid being that person who would follow someone off a proverbial cliff, and yet we’re so quick to squeeze into skinny jeans and get lost in pattern all because someone told us that’s what we should be wearing.

I, for one, remember when wide-leg parachute pants were trendy. I remember loving them; they couldn’t come baggy enough. And yet, when I think back, was I ever comfortable wearing pants that I could have easily lent to a birthday clown? No. Did I get a thrill from pulling them up every two minutes from around my knees? Probably not. And most importantly, did I look good? Negative. But at the time I didn’t know myself, let alone my personal style, and it was easier to be safe than sorry, even though my sartorial insecurity probably made me stand out even more.

And therein lies the key to being a trendsetter in life and in fashion: confidence. If you were to look at the major players of the past hundred years—anyone from Robert Redford to Michael Jackson, Katharine Hepburn to Lady Gaga—they all embody a certain confidence: The assurance of knowing what works for you despite what everyone else is doing. The strength to light your own path and walk it with conviction. The credence that beauty and sex appeal come from within despite how easily we may be led astray.

When I see young girls spilling out of night clubs teetering around in sky-high heels and undersized tube dresses, I just wish they realized that straying from the flock and dressing in clothes that flattered their bodies would provide them with a confidence that far outweighs the presumed sexiness of an exposed ass cheek.

In fact, I wish I could have given myself that advice when I was growing up and more concerned with fitting in than embracing my differences. It would have spared me about a decade of unflattering photos and a closet full of clothes that would have you wondering how, where and why?

All things considered, who would have thought that the one trend that doesn’t go out of style isn’t an article of clothing but rather a state of mind? It’s not something that can be bought, but rather something that’s discovered. A little confidence can make the simplest of T-shirts look like a million bucks. It took Denim Dan a long time to figure that one out, but he’s glad he did. It has saved him some money.