Why Fashion Rules Are Finally Going Out Of Style

My mother is an adventurous dresser — but she hasn’t always been. When she moved to the heartland of America in the late ‘80s from China, her otherness was only highlighted by the blonde, bronzed women around her. She got rid of her prim dresses and the quirky accessories she used to collect in the underground flea markets she frequented back in Jinan, and adopted the classic American uniform of baggy T-shirts and mom jeans. Mission: Be American, blend in, and hope no one notices you're still sort of doing it wrong. It's only over the past 10 years that she has rekindled her love for fashion. Weekly trips to the mall have not only supplied her with a bursting wardrobe, but a new confidence as well — she maintains that she’s responsible for making backless dresses a thing in Eden Prairie, MN, (and everyone knows it). And while she might be the oldest woman in her department at work, she’s also the company fashion plate, and far from invisible.

Last year, while on a cruise with some of her friends, she called me, clearly upset: “Some woman said to me today that I was dressed inappropriate,” she said quietly. “She said women my age should not wear short dresses, and the other women on the boat said they could see my butt.” She paused, and I got ready to pitch a fit. I was ready to fly to whatever island in Alaska she was docked at to rain hellfire down on whatever jellyfish of a woman had elicited a tone from my mother that I hadn't heard in decades — did it really take one rude comment to unravel 30 years of cultivating a backbone? And knowing my mother, it wasn’t like her to back down. She continued, “I told her, ‘Okay, but I am wearing shorts under my dress, and you could never see my butt — so you’re a liar. Also, you don’t have to like my clothes. I don’t like your clothes, either!'”

There she was!
Designed by Isabel Castillo; Photo: Richard FRIEMAN-PHELPS/ Getty Images; Photo: Richard FRIEMAN-PHELPS/ Getty Images; Photo: Laszlo Willinger/ John Kobal Foundation/ Getty Images; Photo: by Sasha/ Getty Images.
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Not following the fashion rules has given my mother a bigger, fuller, more honest voice than when she was drinking the Kool-Aid. But it's following fashion rules that largely defines this time of year. Traditionally, now is the time when the fashion industry churns out massive September issues and the fall fashion package — thick, heavy rulebooks filled with road maps to achieving “the look” — giving select trends, designers, shapes, and vibes the thumbs-up or thumbs-down. Follow along, and you’re in. Can’t keep up? Better luck next season. These issues are fashion publications' biggest moment of the year, coupled with the upcoming Fashion Week, where industry insiders jockey with each other for better seating, better access, and better treatment than their peers. But it’s important to acknowledge that you don't have to play by their rules to appreciate fashion.

As an immigrant woman in her mid-50s living in a homogenous neighborhood, my mother believes that having a unique personal style is intimately related to her sense of self. But the concept of personal style is relatively new. Back in the days when clothing was either handmade or rarely bought, having a distinct "thing," or look, was reserved for the very, very rich. Having a thing meant that you had many things, and sartorial renegades were mostly limited to choosing the only other option available (cross-dressing), or embracing extreme opulence (à la Marie Antoinette).

But with the advent of mass production came the birth of personal style. For the first time, people had the ability to change their clothes as frequently as they wanted to. From those daring pants-wearing women who risked arrest in Paris in the early 1900s in the pursuit of freedom, to London punks who rejected propriety in favor of thrift-store excess, it's breaking the rules rather than following them that's arguably been the more propelling force pushing the fashion world forward.
Designed by Isabel Castillo; Photo: Michael Putland/ Getty Images; Photo: SGranitz/ WireImage/ Getty Images.
These days, clothing is more accessible than ever before, and even those in the most remote locales can place an online order for a garment that costs less than lunch and can be delivered in a flash. People are spending less money on clothes than their grandparents did, but buying more of them: A study conducted by The Bureau of Labor Statistics concluded that Americans spent 4% of their salary on clothing in 2003, compared with 12% in the 1950s, and a Cambridge University study found that the average woman owns four times as much clothing as her 1980s counterpart. With the average woman having access to a wider variety of clothes at lower price points (I'm looking at you, Mom), it’s easy to understand how dressing can be a recreation instead of just a mere necessity.

If clothes are what you wear, style is how you put it together, and the arrival of affordable, accessible fashion gives people a language to express themselves. But what, exactly, are they saying? For one, they’re tired of looking like everyone else. Ever since the recession that hit in 2007, there's been a sustained backlash to the cult of uniform exclusivity of the early 2000s. Consumers rejected the mean-girl clones of Abercrombie + Fitch in such droves that the company was forced to amend its brand strategy. The demise of American Apparel's brand of hipster “cool” is a result of the world's refusal to look like solid-colored, jersey-clad look-alikes.

People are also tired of being told they can’t wear something, as Mama Wang knows. There are stories every week about young women standing up to arbitrary, sexist dress codes, including a troupe of middle schoolers who staged a protest over their right to wear crop tops (their very valid argument: there has been too much onus put on girls to police their bodies, and not enough on boys to police their own attention). There’s also 87-year-old Instagram sensation Baddie Winkle, who is famous because she doesn’t dress her age — choosing to outfit herself in a marijuana-emblazoned, rainbow-colored, midriff-exposing wardrobe over muumuus and cardigans. (Winkle says about her haters, "I tell them, 'You dress the way you want to. I’ll dress the way I want to. We have different opinions, and isn't that nice?'")

And lastly, women are tired of being told that there’s only one definition of what's Stylish (capital S, intended). Ugly shoes were the most unlikely mass-fashion trend of last year, and magazines nearly had to confess their sins when their own staffers started wearing them. Phoebe Philo’s brand of covered-up asceticism at Céline would have been ridiculed 10 years ago, but she has done more for fashion right now than any other contemporary designer. And after being bullied in school for being “ugly,” Kyemah McEntyre created her own prom dress, which stood out among her peers. McEntyre shared, “Don’t let anyone define you. Beautiful things happen when you take pride in yourself.”
Designed by Isabel Castillo; Photo: D Dipasupil/ Getty Images.
Definitions are changing all around us, and concepts that used to be clear-cut are becoming as multifaceted as the people who embody them. Conversations about what things like love, gender, race, religion, and personhood mean are finally being applied to legislation, allowing broader personal freedoms to be put into practice. For the first time in our recent history, there’s a common understanding that we should have control over our own identities in their most basic forms, and we need to be asking the questions to get us there: Can I be a single woman, a mother, and a CEO? Can I be religious and a feminist? Can I choose to be a man, a woman, or reject gender altogether? Logan Jackson, creative director of new agender fashion publication You Do You, says, "The [genderless fashion] movement means that once there are less boundaries in what we can wear, the way we deal with our identities will potentially become so different in a very interesting way."

Fashion plays a big role in helping us ask those questions. After all, it can be the first step toward actualizing the person that you want to be (you’ll hear many variations of “fake it till you make it” in the stories we’ll feature this week). But it’s also one of the most powerful ways to declare to the world your point of view. Many women in the public eye with brave, unique perspectives have used clothing to tell their stories — from news-making Caitlyn Jenner, who used fashion as part of her public transformation that pressed America to second-guess its own prejudices, to a more simple gesture from Solange Knowles, who asked her wedding guests to celebrate the occasion with her by all wearing white, too. And for every pop culture example, there are millions of smaller, private moments of rule-breaking and rebellion that take place in front of our own closet doors.
Designed by Isabel Castillo; Photo: Kevin Mazur/ WireImage/ Getty Images.
Of course, dress codes still exist in many spaces and for many women — and they aren’t going away any time soon. You still can’t wear a crop top in most corporate settings; “Your clothes shouldn’t speak for you” is a maxim that still applies in many offices. There are going to be traditional brides who consider a wedding guest wearing white as profoundly disrespectful. There are workspaces and places of worship where you have to sacrifice personal liberties, such as how you behave, what you say, and how you dress, if you choose to participate. Etiquette expert Lizzie Post (Emily Post’s great-great-granddaughter) explains, “I see people still dressing up for formal occasions, but I also see many more formal occasions trying to cultivate a more relaxed vibe. There are plenty of options that allow you to have your own personal style without sacrificing formality.”

But it’s when the rules feel arbitrary — like Instagram’s sexist no-nipple policy, a prom that allows men to wear pants but not women, or getting outfit-shamed on some boat because some random woman's idea of appropriateness gives her the gall to hate on your leopard-print tunic dress — that fashion maxims are being questioned, criticized, and then flouted. “There are always going to be naysayers,” says professional piercer J. Colby Smith, who is perhaps singlehandedly responsible for making facial piercings mainstream. “But if you’re making yourself truer to yourself, and doing the things you want to do to the body, who cares. I see accountants coming in and getting their septums pierced, and 50-year-olds coming in and getting things done. It’s just become so much more acceptable.”

That's not to say that there's not a dark side to it all. Stores whip through trends at a breakneck pace to serve more people with more fickle tastes. Media coverage of “inappropriate” clothing may seem to do nothing more than pit the new generation against the old. And to pessimists, the prevalence of selfies, #OOTDs, and personal-style blogs are symptomatic of our obsession with vanity. And yes, using clothing as a tool for self-discovery can be as wasteful as it is powerful. There are hugely urgent issues regarding fast fashion that need to be addressed, and more than valid conversations about propriety, over-sharing, and the outrage machine that warrant careful attention. But the pursuit of self does not have to come at the expense of all these other things.
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Designed by Isabel Castillo; Photo: Larry Busacca/ Getty Images.
And it seems that even The Man (or, rather, The Fashion Editor) has wised up, too. For every dogmatic tagline on one magazine’s cover (W ’s August 2015 issue: “Fashion to Follow”), there is another to counter it (Glamour ’s August 2015 issue: “Break the Fashion Rules”). Marie Claire U.K.’s September issue asks you to “Style it your way,” Elle U.K.’s cover star is described as a “Rule Breaker,” and Vogue’s cover promises to showcase the “Rule-Breakers Defining the Way We Dress Now.” And within those pages, there are echoes of the underdog, do-it-yourself language familiar to personal-style blogs, in the form of honest essays and private-gone-public Instagram-style captions. But of course, all this comes interspersed between columns telling you what to keep and what to toss, the trends from the runway that’ll make your legs look longest, and a myriad of other dos and don’ts.

No publication can divorce itself entirely from having to make calls about what's in and what's out (even when those ins and outs seem totally inconsistent from season to season). Just as it is for individuals, having personal taste is important to a brand and those who relate to it. We’ve been guilty, too, of laying down arbitrary laws without a more compelling reason than “because we say so,” but we're dedicating this week to making the case that it's time to retire that concept. We'll be sharing a range of stories about people who decided that the rules aren't really for them, and why that perspective on fashion is more fulfilling than anything you can find through fitting in and falling in rank.

As for Mama Wang, she's discovering more about herself and her capabilities every day. She recently went on a hiking vacation with her friends to national parks across the Southwest, and while everyone else dressed in cargo pants and cotton tees, she made the trek in brightly colored silk blouses and eclectically printed pants. "The world is so beautiful and colorful," she texted me when I commented on one of the pictures she sent me. "I wanted to match it!"

For more ways to fuck the fashion rules, click here.
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