Valuable Life Lessons From Legendary Photographer Bill Cunningham

Photo: Getty

Photographer Bill Cunningham, who shot on the streets of New York and Paris for decades — 40 years for the New York Times alone — died from complications of a stroke. He was 87. And as much as his photography has influenced an entire industry for generations, Cunningham’s unwavering focus on his craft and his rather zen-like approach to life (some might have called it eccentric) can influence any of us, whether we call ourselves sartorialists or not.

While Cunningham might be gone, it’s clear from the deservedly adulatory coverage of his life that he was a legendary artist who will continue to inspire us for years to come. Here are the most impactful Cunningham-approved ways to inspire and influence you in your passions and pursuits.

Don’t Let Your Career Path Be Too Straight and Narrow

While Cunningham always had a penchant for fashion, he didn’t start out wanting to be a world-renowned photographer. He began his career making hats. He was no slouch in that department — among his clients were both the rich and the famous. Which makes the idea of his switching to photography all the more illuminating, yet it’s where his passion led him and mostly by circumstance. He’d been making hats and writing about fashion for more than 15 years before a camera gifted to him pushed him into taking the pursuit seriously in the mid-1960s.

Find Your Perspective, and Stick With It

Fashion photography, just like any other creative passion or professional field, is a crowded world. Cunningham’s solution to standing out and making a name for himself came not just by thinking up a new approach, but by putting in the hard work on the streets to validate that vision, feed it with new material, and constantly learn. “You’ve got to stay out there and see what it is … You’ve got to stay on the streets and let the street tell you what it is,” Cunningham said. This goes for us all: Get out there where the work is, and get dirty to find your path.

Seek Opportunities in the Midst of Calamity

As he detailed in the 2011 documentary Bill Cunningham New York, he loved shooting street fashion in the middle of rainy days. “The minute it starts raining, it’s a whole different scene … When there’s a blizzard is the best time,” he declared in the film. When most would duck and cover or seek shelter, Cunningham knew he could find people at their most natural, unposed, and “without airs.” Before you’re ready to call it quits because of unwelcome conditions, think of the opportunities you might have missed otherwise.

Minimize Unnecessary Decisions

Cunningham’s lifestyle was notoriously sparse. Ironically enough, he wore practically the same clothes day after day. He was easily recognized by his bright blue utility jacket, a pair of nondescript slacks, and plain black sneakers. He also ate the same breakfast every morning at the Stage Star Deli on West 55th Street in midtown Manhattan. Just like Cunningham, some of the most powerful people in the world — Obamas and Zuckerbergs, for example — constantly seek ways to eliminate decision fatigue by setting up as many routines as they possibly can. Do the same and you may find your mind opening up to creative opportunities.

Live Simply

Cunningham was also well known for having a rather minimal home. He spent years in a studio in the Carnegie Hall building, his bed propped up on books and his only other furnishings rows and rows of file cabinets. The place didn’t have a bathroom, kitchen, or closet. No one says you need to live a monk’s life to be successful or focused, but based on the sheer amount of work — and pleasure he derived from the work — Cunningham’s spartan lifestyle should be a reminder that it’s always worth examining exactly what kind of material distractions you’re letting into your life. Are you piling too much on?

Do You Choose Money or Freedom?

Our relationship with money can have a much deeper effect than how deep your pockets feel. Cunningham’s own view was that doing things for money alone compromised too much for him. One of his mantras: “If you don’t take money, they can’t tell you what to do, kid.” Of course, we all need to earn a living, but it’s also important to recognize what we’re doing for love, what we’re doing for money, and what we’re giving up for either one. For Cunningham, freedom was the most precious thing, and he was not willing to sacrifice his for a check. What will you never compromise on?

Be Kind and Fair

There is no industry that bears a greater reputation for backstabbing and tearing people down than the fashion industry. That’s why it’s so refreshing to hear that such an icon in that world was a kind, honest man. One of his biggest falling-outs, with Women’s Wear Daily, was when a fashion spread he created was edited to make fun of the everyday women featured in his images. He wouldn’t stand for it, and it haunted him for years. That sense of fairness and openness spilled over into Cunningham’s street photography as well. He was as fascinated by street wear as he was by haute couture — by black, brown, and gay people as he was by straight, rich, and white.

Don’t Try to Be Something You’re Not

Most remarkably, Cunningham never claimed to be a great photographer. What he did claim to be was a witness to people, the clothes they wear, and the way they live. He never attempted to bill that pursuit as anything more than it was. “The problem is I’m not a good photographer. To be perfectly honest, I’m too shy. Not aggressive enough. Well, I’m not aggressive at all. I just loved to see wonderfully dressed women, and I still do. That’s all there is to it.” Above all, it seems, knowing yourself and being true to yourself pay off.

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