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In the ever-evolving world of fashion, the rules and guidelines that once governed men's clothing are now seen as relics of a bygone era. This shift, a reflection of the spirit of the times, has been observed in various corners of the fashion landscape.

As far back as 2013, Zadie Smith, in her essay collection Imitations, noted a growing strain of hyper individualism among her NYU students. This trend was evident not only in the writing and creativity context but also in the way these young individuals expressed themselves through their personal style.

The television show "Mad Men", which was in its penultimate season in 2013, depicted a time when men's fashion was characterised by chinos, polished brogues, blazers, and folded pocket squares. In London during the same year, it was common to see men dressed in a style reminiscent of "Mad Men" characters. However, the conformity and lack of irony in men's fashion, often referred to as the #menswear era, is now considered an aberration or peak Millennial cringe.

The year 2020 marked a significant turning point in fashion. On one hand, Covid-19 made dress codes redundant for 2 to 3 years, forcing a reevaluation of traditional norms. On the other hand, the ugly trainer trend became prominent, signaling a rejection of conventional aesthetics.

The concept of 'Dad core' emerged as a fashion trend, symbolising a move towards comfortable, casual clothing that was both practical and stylish. This trend, along with the growing acceptance of not following fashion rules, is seen as a gesture of empowerment for the current generation.

In 2025, the spirit of fashion seems to prioritize individuality and self-expression over conformity and traditional fashion norms. Justin Bieber's disregard for fit, color coordination, and overall effort in his clothing is interpreted as liberated and edgy, rather than lazy and not very nice to look at.

Carolyn Bessette-Kennedy, with her timeless, minimalist style, represents the generation under 40 in 2025 when it comes to thinking about clothing. Her style, which continues to inspire and be emulated by young people today, embodies the ethos of personal style over conformity.

The rise of social media platforms like Tumblr and Instagram in 2013 provided a new stage for men to showcase their fashion, further fueling the trend towards individuality and self-expression. In 2025, not following fashion rules or guidelines is considered more acceptable than adhering to them, especially for those under 40.

This shift in men's fashion reflects a broader cultural movement towards personal freedom and self-expression. Smith's observations about individualism extend to how the current generation thinks about their personal style in fashion. The fashion world, much like the writing and creativity sphere, is becoming a platform for self-expression and a means of asserting one's identity.