To obtain the object of my desire I’d have to steal it. There it was in the pro shop of the Los Angeles Tennis Club, a white sweater vest adorned with the classy Fred Perry laurel wreath logo. It was the same piece of clothing Jimmy Connors had worn in 1974 when he’d attained the number one ranking, a perfect fit for my nascent tennis sensibility, wedding British tradition and American swagger.

I was 14 years old and had just lost in the first round of the 1975 Southern California Junior Sectionals. Ticked off by my rapid defeat—I’d reached the third round at this event a year earlier—I was also mad at the tennis establishment. The LA Tennis Club may have billed itself as “The Cradle of Champions,” spawning such stars as Ellsworth Vines, Bobby Riggs and Jack Kramer, but it had a long history of discrimination against Jews like me, its elitist leadership personified by the J. Edgar Hoover-like Perry T. Jones. Though Jones had died five years earlier, his legacy endured.

So in short order I rationalized that my criminal act was justified in the name of democracy. But how to pilfer? In those days, players virtually lived out of their racket covers. The vest would noticeably bulge.

But I had something better. Years before the emergence of bags that could house a body, my mother had bought me one a little bigger than those that contained bowling balls. I slid towards the pro shop counter where the vest sat and pushed the vest into the bag. Take that, Mr. Jones.

Save for tennis apparel, I’d rather visit the dentist than shop for clothes. It was always good over the course of 28 years together that my late wife Joan, a former art director, had a keen color sense and was adept at calling catalogue companies.

But when it comes to tennis, logos and collars and zippers and colors excite me. My current lucky big match shirt is the blue Nike dri-fit with the mildly shiny collar I bought after seeing Roger Federer practice in it six years ago at the ATP Tennis Masters Cincinnati tournament. Red summons exceptional emotion for high-stakes league matches and contemptible opponents. Orange works for sunny days and friendly doubles.

To live in Northern California—where temperatures generally range from 55 to 65 degrees—is a warmup suit lover's paradise. There's the retro blue three-striped adidas suit Joan hunted down that makes me feel like a star from the ‘70s, the white jacket with the Longwood Cricket Club logo I bought during a Davis Cup tie, the black Fila I won in a friendly wager with a former pro who questioned my historical knowledge.

Occasionally, though, my appetite has backfired. Once in the Philippines I bought four Ellese shirts, three pairs of shorts and a sweater for a mere $200. Turned out the price was indeed too good to be true. These proved to be black market versions. Within a month, all disintegrated in the laundry. Another few hundred bucks at a Fred Perry shop in London went down the drain when I learned the hard way that a size medium in Europe is closer to a small in America.

My desire to wear high-quality tennis clothes goes back to when I first began to play tennis in the early ‘70s. The color explosion of the counterculture had spread across America, the term "in living color" personified by NBC's peacock logo. Tennis' boom years coincided with this broadening of the spectrum. Suddenly a sport that was lily-white for decades opened up in all shades of the rainbow.

At the 1974 US Open—where Connors draped his white Fred Perry vest over a devilish red shirt—defending champion John Newcombe conducted his business in a tidy pink shirt adorned with Newcombe’s distinctive logo: a face boasting a mustache and one eye. Cheeky wink or swashbuckling pirate? The Newcombe logo personified everything I wanted to be on the court—regal, self-assured, classy, just a dash irreverent and thoroughly in control. A year later, I at last convinced my mother to buy me the pink shirt.

As ex-pro and psychologist Allen Fox wrote in his 1979 book, If I’m the Better Player, Why Can’t I Win?, “No one genuinely believes that the spirits of Borg and Connors actually inhabit the tennis clothes that bear their names on the labels. But by buying and wearing these clothes many people, believe it or not, practice a certain kind of animism—one that can often be seen in the behavior of young children.”

Fox went on to explain how donning a Superman-like cape as a child helped him feel he had exceptional power.  Bingo. I’d learned the game at public parks and honed my strokes much more through the pages of TENNIS magazine than private lessons. Broadcaster Mary Carillo once described my technique as “cultivated caveman.”

While I won my share of matches at local park events, junior tournaments were a whole other challenge. My first year of junior tennis I lost in the first round of eight straight tournaments. But a year before I stole the Fred Perry vest, I’d at last broken through with those two wins at the Los Angeles Tennis Club.

The great juniors of my Southern California childhood had many approaches to matters of wardrobe. Vince van Patten often showed up with one uncovered racket and a white T-shirt. Ill-prepared idiocy or sheer confidence? Van Patten was the latter. Eliot Teltscher favored a shirt so baggy and wrinkled it look like he’d just plucked it from a yard sale. It hardly mattered, as in rapid order Teltscher would snap, crackle and pop his way to one victory after another. And then there was Walter Redondo, who at the age of 16 conveyed elegance in everything from his walk to the way he carried his rackets to his crisp, collared shirts. Ask anyone who played junior tennis in Southern California during this time and they will emphatically nod “yes” if you compare young Redondo to a teen prototype of Roger Federer.

So my thinking was that my disheveled game needed to be trumped-up, that the classy clothes of the world’s best would confer at least some degree of regal stature and competitive aptitude.

Six months after acquiring the Fred Perry vest, I wore it when I walked on Court One at UCLA to play a high school challenge match that would determine if I would play singles or doubles on our team. This also happened to be the same court Connors often practiced on when he came to UCLA for frequent hitting sessions. Down 3-0 in the decisive set, I rallied to win it in tiebreaker.

Writes Fox, “Being well-turned-out should also be seen as a statement of your commitment to the match. If you are taking the match seriously, then it is logical you prepare for it seriously. That includes taking care with your appearance; it is a show of respect to yourself and your opponent.”

A recent rival named John B saw it quite differently. “You wear a collared shirt like that every time you play?  Real athletes where T-shirts!” Of course I begged to differ, Fox’s words echoing in my head. Perhaps even more odd, I pointed out to John, was that we each had our respective theories, were each keen on asserting our respective Superman-in-the-cape concepts.

The contraband Fred Perry vest still sits in my dresser. Thirty years after my shoplifting moment, a good friend, former pro Trey Waltke, was the manager of the Los Angeles Tennis Club. He too has a fashion sense—once wearing long white pants to compete at Wimbledon. I couldn’t help but confess my crime to him, pointing to the spot in the pro shop where I’d snuck off with the vest. We arranged a barter so I could work off the penalty for my crime. Today I walk the world a free man. And tomorrow feels like a blue shirt day.

Joel Drucker is the author of Jimmy Connors Saved My Life.**