I once owned a really, really ugly pair of white leather boots.

"I once owned a really, really ugly pair of white leather boots. They were so bad. It was back in the '80s! It was just a really tacky fashion choice when I was in middle school, and I thought it was cool. I'm really embarrassed." These words, spoken by Jordana Brewster, reflect the universal experience of youthful exuberance, self-expression, and the inevitable embarrassment that accompanies certain choices in hindsight. Brewster’s recollection of the white leather boots symbolizes how we, at times, embrace trends and fashion choices based on what feels right in the moment, only to look back years later and realize how misguided those choices might have seemed. Yet, within this moment of embarrassment, there is a deeper understanding—one of growth, self-awareness, and the process of maturing into a more refined version of ourselves.

In the ancient world, the pursuit of style and fashion was no less significant than it is today. The Romans, for example, were known for their elaborate togas, intricate jewelry, and distinctive footwear, which not only reflected their wealth and status but also their identity within society. However, just as Jordana Brewster reflects on the tacky fashion choices of her youth, the ancients also had their own moments of self-reflection and regret over past decisions. The philosopher Socrates, who emphasized self-examination, would likely have viewed these moments of embarrassment as opportunities for personal growth and wisdom. In his dialogues, he often asked people to reflect on their past actions, to learn from them, and to strive to become better versions of themselves. This understanding of self-awareness is integral to Brewster’s quote—what may have seemed cool in the past is a stepping stone toward greater wisdom.

The story of Emperor Nero provides an example of someone who, like Brewster, might have indulged in temporary pleasures or choices that, in hindsight, did not serve his greater legacy. Nero, known for his extravagance, fashion choices, and lavish lifestyle, pursued trends that were intended to impress but ultimately left him remembered for his excesses rather than his wisdom or leadership. His story serves as a cautionary tale of how fame, style, and fashion—when driven by the desire to impress others or to conform to fleeting trends—can overshadow more important qualities, such as integrity, humility, and genuine leadership. Brewster’s moment of embarrassment with her boots serves as a contrast to this idea—while Nero may have been driven by an obsession with his outward image, Brewster is able to reflect on her past choices with a sense of humility, learning from them rather than being trapped by them.

Consider also the story of Alexander the Great, who, despite his immense power and conquests, was known to wear the simple robes of a philosopher. Alexander, unlike Nero, chose to present himself in a way that was not obsessed with the external, but rather focused on internal greatness—on courage, wisdom, and strategy. His decision to embrace simplicity in his dress was a powerful statement against the excesses of others. This insight can serve as a lesson from history: while outward appearance and fashion choices may offer momentary pleasure or status, true greatness lies in one's character and the choices that serve to cultivate self-growth and wisdom. Brewster, in her reflection on the ugly boots, illustrates the process of growth—acknowledging past mistakes, embracing the lessons they offer, and ultimately maturing into a more authentic version of oneself.

Brewster’s quote also speaks to the nature of time and how, as we mature, our perception of what is cool or valuable changes. In the same way that Plato spoke of the immaterial nature of wisdom—which only grows through experience—Brewster’s reflection offers a parallel. As time passes, we are able to look back on choices that once seemed right, only to see them with a more critical eye. This ability to recognize growth and self-improvement over time is a key element of the human experience. The process of learning and evolving involves looking at the past with compassion and humility, understanding that our earlier choices—though they may seem misguided or embarrassing now—were an essential part of the path toward greater self-awareness and wisdom.

The lesson in Brewster’s moment of embarrassment is not one of regret but of acceptance and self-compassion. Just as the ancients revered the pursuit of self-knowledge, we too must learn to look back on our own past actions with understanding rather than judgment. The ugly boots that Brewster once wore are but a symbol of the moments in all our lives when we took steps in the wrong direction, not out of malice, but out of the desire to fit in or express ourselves in the best way we knew at the time. These moments are not failures but milestones on the journey toward greater authenticity and wisdom.

In our own lives, we should not fear the embarrassment of past choices, but instead embrace them as part of our unique journey. The ugly boots, the questionable fashion choices, and the regrets are all part of the process that shapes us into who we are meant to be. Rather than hiding from these moments, we should celebrate them, knowing they reflect our growth and transformation. As we move forward, let us remember that true style comes not from the clothes we wear or the trends we follow, but from the confidence with which we embrace our evolving selves and the wisdom that comes with embracing our past as part of our journey toward becoming our best selves.