A Case For Dressing Like The Boys Of The Sandlot

Soft Focus is a monthly column about how clothes make a movie. For each installment, David explores how wardrobe contributes to a film’s impact, mis-en-scene, and culture at large.

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I probably saw 1993’s The Sandlot directed by David Mickey Evans, for the first time somewhere in the middle of the steroid era… Let’s say 2001.

In the 2000s, ESPN told me that baseball players were cheaters and liars, and I’d eat my breakfast patiently waiting for Stuart Scott to get through dissections of The Mitchell Report and highlights of congressional testimony so I could see 15-second flashes of an Allen Iverson crossover or a Vince Carter tomahawk.

Baseball felt “serious” and old-timey. It was something my Grandfather, who was a bat boy for the Chicago White Sox and a proud owner of a Babe Ruth-signed baseball, might yammer on about. I wouldn’t understand a single word. I thought, rather naively, that baseball was not as expressive a game as the sports that dominated my interest as a kid– football and basketball.

Upon the first time watching it, The Sandlot lodged itself in my heart immediately, as it did many boys my age. Smalls, the new kid to the neighborhood, joins a gang of merry baseball hooligans, and with him as the ninth, they can field an entire team, even if Smalls is the weak link. At its core, the film is about friendship and family, mischief and monkey business, the American century, and its beloved pastime.

There is a scene between Smalls and Benny Rodriguez (or Benny the Jet as his friends call him admirably) where, after a failed first day on The Sandlot full of excruciating unforced errors, Benny gives Smalls a piece of advice. Smalls is wearing khakis shorts, a short sleeve button-up shirt buttoned to the top, and a long-billed fisherman hat – a total square or L-7 weenie, as the boys would say. It's a simple suggestion that will help him become part of the gang, “bring a tee shirt and jeans tomorrow, okay?”

Throughout the film, we follow this gang of rascals hatch schemes to kiss Wendy Peffercorn, the local lifeguard with a red one-piece and a red lip and bow to match, defeat the arrogant local little league, and most importantly, retrieve Small’s stepfather’s Babe Ruth signed baseball from the ferocious Beast – an english mastiff that lurks behind the outfield fence.

Grania Preston served as the films Costume Designer and went on a hell of a hot streak in the early '90s with The Mighty Ducks, The Sandlot, Cool Runnings, and D2: The Mighty Ducks – all films I would vaguely call “feel-goods-sports-movies-for-kids-under-two-hours-perfect-for babysitting-a-pair-of-siblings-ages-six-and-ten.”

Of those four films, The Sandlot is their most subtle but best work. The clothing choices are essential for establishing the gang as a single team but distinct enough to give each character their personality. They have a uniform — selvage jeans, dusty shirts, and canvas sneakers — but there is variation within that uniform. Squints, the wise-cracking shortstop, sports patterned buttons ups and black-rimmed glasses. Yeah-yeah, the third baseman, rocks cut-off tees and undone baseball jerseys, while the catcher, Ham, wears pleated shorts or jeans with a classic horizontal striped tee.

They each dawn different hats flashing their allegiances: Benny with a clean blue Dodgers hat, Ham and others with iconic black Yankees caps, and pitcher Kenny “The Heater” with an especially fresh Kansas City Monarch cap.

Their individual yet cohesive styles is most visible when they play the local little league team in a grudge match. The opposing teams’ pristine pinstripes and matching socks look stiff, formal, and ultimately to grown up. When the boys pummel them in Chuck Taylors and tee shirts, it makes the opposing team’s uniforms look like costumes – unworthy of the game itself.

In the mix are other hallmarks of mid-century American style – overalls, camp-collared shirts, and terry cloth polos have the boys looking like they are posing for an album cover or a Brendan Babizein-era J. Crew shoot – maybe even sipping some High Lifes and smoking darts at fake-dive-bar Ray’s.

Why do I feel like, whenever I’m scrolling through the plethora of TikTok fashion guys I follow, or when I walk through the Lower East Side or get dinner in Brooklyn, every man is dressing like a boy from The Sandlot? And more importantly, why is it working?

Preston’s mission was simple but delicate. They needed to create a well-worn and battered wardrobe that could convince the audience that these boys have been at The Sandlot all summer – almost frozen in amber, a symbol of American boyhood itself. How do boys dress? Effortlessly. I mean that literally — with little to no effort. They grab what is within reach. Wear whatever shirt or pair of jeans you feel comfortable getting dirty, one your mother won’t mind if you get sweaty or dusty.

There is a desirable nonchalantness in dirty Converse, thrashed baseball jerseys, and raggedy mits dangling from their hand that becomes difficult to exude as you get older and stiffer and become concerned with rent and dental insurance. There is a certain slouchy uncomplicated coolness that comes with boyhood. In The Sandlot, the boys live the perfect moment of unappreciated clarity of youth where they know themselves but not so much as to suppress their individuality.

It makes sense that men, including myself, find themselves flocking back to the garments of their own personal sandlot, black top, or grassy field. There is a pull to return to your earlier sartorial impulses because after learning more about what you like and who you are, you often learn that your first thought was your best thought. You reach for the perfect jeans and beat-to-death tee shirt the same way you reach for an album that you appreciated from your teenage years.

At the climax of the film, when Benny decides to play hero ball and hops over the fence and uses his speed and agility to snatch the Babe Ruth ball right from the mouth of the Beast, he laces up a brand new pair of murdered out PF Flyers and transforms into The Jet. At the end of the movie, we see Benny, a grown up player in the MLB, stealing home with the Dodgers logo on his chest instead of his cap, while Smalls calls the game from the press box in the same dorky fisherman’s cap from earlier.

They have become the men they were destined to become, but still sport totems of their childhood and their perfect summers.