I still remember the exact moment I realized fashion rules were made to be broken. I was 22, fresh out of college, at my first real fashion week assignment – a show for a designer whose name I was still practicing how to pronounce. Standing outside the venue in a vintage blazer, nervously checking my phone to avoid eye contact with the intimidating crowd, I spotted her: a woman in her 60s with a silver bob, wearing navy blue with black – deliberately, confidently, gloriously.
Navy and black. Together. The ultimate fashion “don’t” that had been drilled into my head since I was old enough to dress myself. My mother would sooner wear pajamas to church than mix those two colors. Yet here was this woman, sailing through the crowd in a navy suit with black leather accessories, looking so chic that people were literally stepping back to let her pass, like Moses parting the Red Sea but with better shoes.
I followed her – partly because she seemed to know where she was going (I did not) and partly because I was mesmerized by her flagrant disregard for what I thought was an unbreakable style commandment. As luck would have it, she was seated in the same row as me, close enough that I could see her navy suit was actually trimmed with black, making the combination even more deliberate.
“Excuse me,” I whispered as we waited for the show to start, my journalistic curiosity overcoming my social anxiety, “your outfit is amazing.”
She turned, assessed me with the kind of quick, knowing glance that told me she’d been in this industry longer than I’d been alive, and said simply: “The secret to style is knowing which rules to break.” Then she turned back to the runway, leaving me with what would become my fashion philosophy for the next decade.
I’ve thought about that woman countless times over the years as I’ve watched the fashion world’s “mistakes” transform into trends, then into classics. Navy and black? Now a no-brainer color combination endorsed by everyone from Phoebe Philo to J.Crew. Socks with sandals? They’re all over the runway. Clashing prints? An art form. Double denim? Chic again (though please, let’s not call it the Canadian tuxedo – our northern neighbors have suffered enough).
What I’ve come to realize is that these so-called mistakes, when made deliberately and with confidence, aren’t mistakes at all – they’re power moves. They signal to the world that you know the rules so well, you’ve earned the right to break them. That you dress for yourself, not for an outdated rulebook. That your confidence extends beyond following instructions someone else created.
Take mixing metals – that old axiom that your gold necklace couldn’t possibly coexist with your silver rings without causing some sort of accessory civil war. For years, women dutifully checked their jewelry before leaving the house to ensure they were mono-metallic. Now? The chicest people I know stack silver, gold, and rose gold with abandon. My friend Emma, a jewelry designer whose taste level I trust implicitly, hasn’t worn a single-metal look in years. “Matching metals is like matching your purse to your shoes,” she told me recently. “Something your grandmother worried about that actually ages you.”
Then there’s the “no white after Labor Day” rule, perhaps the most persistent yet most ridiculous fashion dictate in American culture. Its origins lie in the old-money social calendars of the early 20th century, when summer whites signaled leisure time at resorts before returning to city life in darker colors. Today, winter whites aren’t just acceptable – they’re sophisticated. A winter white coat over cream trousers with an ivory sweater creates a tonal look that’s far more interesting than the sea of black we typically drown in from November through March.
Some of my favorite intentional “mistakes” have become my style signatures. I consistently wear clashing patterns – floral with stripes, plaids with polka dots – using color as the unifying element that makes it look intentional rather than like I got dressed in the dark. I regularly wear sequins before noon, operating on the principle that catching the morning light is actually more flattering than evening dimness. And perhaps most controversially, I refuse to match my bag to my shoes, instead treating my accessories as independent elements rather than conjoined twins who must coordinate their outfits.
These choices weren’t always received positively. Early in my career, an editor pulled me aside after a meeting to inform me that my pattern mixing was “distracting” (code for “we hate it”). A date once asked if I was “on my way to a party” when I showed up to brunch in a subtle silver-threaded sweater. And my mother still purses her lips when I wear navy and black together, a silent protest against my fashion rebellion.
But here’s what’s interesting: the more confidently I embraced these so-called mistakes, the more they became associated with my personal style. The pattern mixing that was once “distracting” is now something I get complimented on regularly. The daytime sparkle has become expected. The mismatched metals look deliberate rather than forgetful. Confidence, it turns out, is the essential ingredient that transforms a fashion faux pas into a power move.
I tested this theory recently at a fashion week dinner, deliberately breaking another sacred rule: wearing horizontal stripes. As someone who’s never been sample-sized, I’d had it hammered into my brain that horizontal stripes would make me look wider and were therefore forbidden. But I’d found a vintage Jean Paul Gaultier striped sweater at a consignment store – one of those holy grail pieces you buy even if you’re not sure when or how you’ll wear it. I paired it with straight-leg jeans and simple black boots, letting the stripes take center stage.
The response was immediate – and universally positive. Three people asked where I’d found the sweater. A photographer asked to take my picture for a street style roundup. The confidence with which I wore the piece transformed it from a potential figure “mistake” into a statement. The stripes weren’t making me look wider; they were making me look like someone who knew exactly what she was doing.
This phenomenon isn’t limited to women’s fashion, either. Some of the most stylish men I know are those who break traditional rules – wearing brown shoes with black pants, mixing patterns and textures in ways etiquette books would frown upon, or ignoring the “seasonal color” guidelines that claim to determine which shades suit which skin tones. My friend Michael, easily the best-dressed man in my social circle, regularly wears pink despite having been told his entire life that redheads “can’t wear pink.” His response? “Watch me.”
What’s particularly interesting about fashion rule-breaking is how quickly the exceptions become the new normal. Things that were once scandalous – white jeans in winter, sneakers with dresses, lingerie as outerwear – are now so commonplace that the younger fashion crowd doesn’t even realize they were once taboo. Fashion, like language, evolves through usage, through the collective decision to try something different and see if it works.
Some of today’s most influential designers built their careers on elegant rule-breaking. Miuccia Prada’s deliberate ugliness, Alessandro Michele’s maximalist pattern clashing at Gucci, Phoebe Philo’s encouragement of comfort without sacrificing style – all of these approaches began as rejections of established norms and evolved into new classics.
So what current fashion “mistakes” might become tomorrow’s power moves? I have my eye on a few: deliberately visible bra straps (not just peeking out, but as an intentional part of the look), mixed athleisure and formal wear (running shorts with blazers is already happening on the cutting edge), and my personal favorite, age-inappropriate dressing – not in the “mutton dressed as lamb” sense, but in the deliberate rejection of dressing “appropriately for your age.”
This last one feels particularly powerful. The idea that certain styles, colors, or silhouettes should be abandoned at specific age milestones is not just restrictive but patently absurd. I recently interviewed a 72-year-old fashion professor who regularly wears platform combat boots, oversized graphic tees, and has pink streaks in her gray hair. “The day I start dressing in beige elastic-waist pants is the day they can put me in the ground,” she told me, adjusting her Comme des Garçons jacket.
For those wanting to experiment with intentional fashion mistakes, here’s my advice: start with one rule-breaking element and wear it like you invented it. Mix navy and black, but keep the silhouette classic. Try horizontal stripes, but in a cut you’re already comfortable with. Wear white in December, but in fabrics appropriate for the season (think winter white wool, not summer linen). The key is to make the “mistake” look deliberate – like you’re breaking the rule because you’ve moved beyond it, not because you don’t know it exists.
Pay attention to proportion and balance – rule-breaking works best when the overall effect is harmonious. My pattern mixing works because I keep the silhouettes simple and ensure the clashing prints share at least one color. The navy and black pairing works because the textures complement each other. There’s method to the madness.
Most importantly, wear it with absolute conviction. Hesitation is what transforms a fashion power move into an actual mistake. If you’re constantly tugging, adjusting, or looking unsure, people will sense your discomfort and interpret your choice as an error rather than a statement. Fashion confidence is a self-fulfilling prophecy – believe it works, and suddenly it does.
I ran into the silver-bobbed navy-and-black pioneer a few years after our first encounter, at a gallery opening in Chelsea. She was wearing red and pink together (another former taboo) and looked just as commanding as she had that first day. I reminded her of our brief conversation and told her how it had shaped my approach to fashion.
She laughed and said, “The most stylish people aren’t those who follow all the rules or those who break all the rules. They’re the ones who know which rules don’t matter anymore.”
I’m still figuring out which rules don’t matter. But in the meantime, I’ll be over here wearing white jeans in January, mixing my metals with abandon, and pairing navy with black like it’s what they were made for. Because sometimes the biggest fashion power move is simply deciding that you make the rules now.