One thing I find myself perpetually interested in is rules. The following of rules, the breaking of rules. Why rules exist, who made the rules, and what gave them the right. Of all the content I’ve seen on here so far this year, the common thread I see is…rules. Buy this, don’t buy this. Don’t buy at all. Keep buying. Buy 5 items only. One in one out. So I ask myself, how did we get here?
The history of style has always been intertwined with the culture and norms of its time, and for those of us who grew up as millennials, that history is particularly complicated. Fashion wasn’t just about self-expression—it was about rules, expectations, and the silent pressure to conform. Even before we were old enough to consciously consider style, the frameworks for how we should look were being built around us, quietly reinforced by the media we consumed, the celebrities we idolized, and the trends we chased.
These influences weren’t subtle by any means. They shaped our understanding of style as a pursuit of “rightness” rather than individuality. They taught us to see our bodies as problems to solve and our wardrobes as tools to fix them. And while some of these influences offered moments of inspiration and creativity, they often did so at the expense of self-acceptance.
TV in the early 2000s had a particular knack for turning personal style into public critique. Shows like What Not to Wear became cultural phenomena, with hosts Stacy London and Clinton Kelly offering a mix of tough love and fashion advice. The premise of the show was straightforward: participants—whose “flawed” wardrobes had been nominated by their friends or family—were given a makeover, complete with strict guidelines about what they should and shouldn’t wear. The visual spectacle of clothing being tossed into trash cans became a recurring motif, symbolizing not just a rejection of old habits but of the participants’ former selves.
While the advice was occasionally practical (invest in tailoring, build a capsule wardrobe), the show’s underlying philosophy was clear: there was a “right” way to dress, and anything outside of that framework was wrong. Style, it suggested, wasn’t personal—it was a skill to be taught, a problem to be fixed. And for those of us watching, the implicit message was equally clear: if your wardrobe didn’t conform to these rules, you were failing too. When it is all about the clothes and not about the person, what’s the point?
London and Kelly have both since made statements acknowledging how the style world has changed since the show aired, but have also said that “there are no more norms” which I think is a delusional thing to say, but I digress.
This theme wasn’t confined to reality TV either. Magazines like Seventeen and Teen Vogue played an equally significant role in shaping millennial style. For many of us, these glossy pages were our first introduction to the world of fashion. They promised excitement, guidance, and an entry point into a world that often felt aspirational and unattainable. Or if you, like me, grew up in a rural area void of culture, offered the only viewpoint through which to experience style. But they also reinforced a narrow view of what was considered beautiful or fashionable.
These magazines were filled with prescriptive content: how to “dress for your body type*,” how to follow the season’s trends, how to appeal to the male gaze. Their quizzes and “rules” created a framework for style that was, at its core, about conformity. And while they occasionally celebrated individuality, it was always within the confines of what was deemed socially acceptable or trendy. The result? Yet another generation of young women who learned to measure their style by someone else’s standards, often at the expense of their own instincts.
*Not that there’s anything wrong with offering advice for dressing a certain body type, this is something Audrey and I do in our own work with clients. But there are ways of approaching this topic from a practical, architectural perspective vs a “let’s hide this problem area” perspective that was far more common in magazines like this.
Celebrity culture amplified these messages, offering a parade of unattainable ideals. In the early 2000s, stars like Paris Hilton, Lindsay Lohan, and Britney Spears defined the aesthetic of the Y2K era – which is back (hooray). Their low-rise jeans, baby tees, and platform sandals became the blueprint for “cool,” even as they alienated those of us whose bodies or budgets didn’t align with those trends. Shows like E! News and magazines like People dissected red carpet appearances with a binary judgment of “best dressed” or “worst dressed,” reducing style to a competition. Because we all have to get dressed to be “better than” the next. /s
Then came the fast fashion boom. Brands like Forever 21 and H&M made trends more accessible than ever, offering a quick, affordable way to emulate the latest styles. But this accessibility came with a cost, as we now know. Fast fashion encouraged overconsumption, devalued craftsmanship, and prioritized quantity over quality. It made it easy to chase trends, but harder to develop a personal sense of style. I remember shopping at Forever 21 in those early days, and even the quality was slightly better than it is now. When I come across “vintage” F21, it feels different to the touch and is often in decent condition, versus the newer items I find that are already in rags and feel paper thin.
Social media platforms like Tumblr and Lookbook.nu added another layer to this equation. They democratized fashion, allowing anyone to share their style with the world. But they also introduced a new kind of comparison culture, where the pressure to “perform” style became constant. This performance of sorts is still what I find most of the time on Pinterest, it’s hard to get away from these days because it is now and may always be the norm to an extent. It reminds me of the concept of art for art’s sake, something I studied in the curriculum for my art history degree. I often wonder about how this has applied to fashion and style; a topic for another day to be sure (I’ll give you time to prepare yourselves for that forthcoming manifesto). These platforms celebrated creativity, but they also reinforced the idea that there was a “right” way to dress—an aesthetic to strive for, a standard to meet.
And, of course, there were the movies. Who can forget the iconic makeover montages of the late ‘90s and early 2000s? Whether it was Julia Roberts in Pretty Woman or Rachael Leigh Cook in She’s All That, these scenes romanticized transformation as a pathway to self-worth. They were fun, aspirational, and deeply entrenched in the idea that style was about meeting societal expectations rather than expressing personal identity. Don’t think for one second I haven’t seen both of these movies at least a dozen times. They both provide some nostalgic comfort, but I can still acknowledge that much of the messaging within both of them is questionable, at best.
Looking back, it’s easy to see the contradictions in these influences. On one hand, they sparked creativity and offered a window into the world of fashion. On the other, they often reduced style to a set of rules that felt impossible to follow. They taught us to see our bodies as projects, our wardrobes as tools of correction, and our confidence as something to be earned rather than inherent.
But here’s the thing: those rules don’t have to define us anymore. The beauty of revisiting this history is that it allows us to see where these ideas came from, how they shaped us, and—most importantly—how we can unlearn them. Each generation before and after my own has had its own set of style rules and influences, no one has been free from that trap. This is one of the biggest things we talk about with our clients, because they all come to Audrey and myself with these deeply rooted ideas of how they should be dressing. That’s why we talk about the power of personal style so often, because in order to unlearn something or to change the way we think, we have to digest new ideas and information on a regular and repeated basis. It’s how we learn anything and everything.
Style doesn’t have to be about following rules or meeting expectations. It can be about self-expression, creativity, and authenticity. It can be about embracing our bodies as they are, rather than trying to fit them into a prescribed mold. And it can be about finding joy in the process, rather than pressure in the outcome.
I’ll leave you to ponder the following: what shaped your sense of style growing up? What rules did you/do you internalize, and which ones have you let go of? Are you in the process of letting go of rules that don’t work for you now? You’re not alone.