How I learned to stop worrying and break every fashion rule my mother taught me

When I was maybe fourteen, my mom handed me this ancient copy of some etiquette manual she’d inherited from her aunt. The thing was literally falling apart, held together with rubber bands and what I’m pretty sure was spite. But there was this whole section on “proper dressing for young ladies” that I became weirdly obsessed with. No white after Labor Day, obviously. Navy and black together was apparently a crime against humanity. Visible bra straps would basically get you excommunicated from polite society. And don’t even think about mixing patterns—that way lay madness and social ruin.

I followed those rules religiously through high school and college. Like, religiously. I had friends who would text me photos of their outfits asking if they were “breaking any Claire rules” because I’d become this walking fashion police officer, enforcing regulations I’d never actually questioned.

Fast forward to last month when I’m at this industry event, standing next to this woman who I immediately clocked as having the most effortless style I’d seen in ages. She was wearing—and I’m not exaggerating—literally every single thing I’d been told was a fashion don’t. White jeans in March (the horror!). A navy sweater over a black top. Three different patterns happening at once. Her bra straps were not just visible, they were like… featured. And she looked absolutely incredible.

That’s when something clicked for me. The most stylish people I know—and I mean the ones who make me stop scrolling on Instagram because their outfits are so good—they’re systematically ignoring every fashion rule ever written. But here’s the thing: they’re not doing it accidentally. They’re doing it on purpose, with this kind of confident intention that makes you realize they know exactly what they’re doing.

I started paying attention differently after that. Started actually asking people whose style I admired what rules they’d decided to ditch. And what I found out was way more interesting than just a list of outdated don’ts.

Take seasonal colors. You know, that whole thing where you’re supposed to wear pastels in spring, brights in summer, earth tones in fall, and basically live in grayscale from November through February? Total nonsense, according to literally every stylist I talked to. This one woman, Sarah, who does wardrobe for some major fashion magazines, basically laughed in my face when I brought it up.

“Those rules exist because of old retail cycles and weird class signaling,” she told me over coffee, while wearing the most gorgeous coral blazer in January. “Like, the whole white after Labor Day thing? That was rich people in the 1920s trying to separate themselves from new money. It has nothing to do with what actually looks good or makes you feel good. I wear bright summer colors in winter specifically because they make me happy when it’s gross outside.”

I looked down at my own outfit—all blacks and grays because it was February and that’s what February clothes look like, right?—and realized I’d been dressing seasonally appropriate without ever questioning why. Who decided January means muted colors? Some fashion magazine editor in 1987? Why was I following that?

The navy and black thing turned out to be equally arbitrary. I met this buyer who works for one of those fancy department stores where everything costs more than my rent, and she was wearing navy pants with a black sweater that looked so expensive I was afraid to stand too close to it.

“Navy and black together is actually incredibly sophisticated when you do it intentionally,” she explained. “It shows you understand subtle color relationships instead of just matching everything exactly. Anyone can wear all black or all navy. It takes actual skill to work with colors that are almost the same but not quite.”

And pattern mixing? Forget everything you’ve ever been told about that. I talked to this designer whose personal style is basically what would happen if a Victorian wallpaper sample book exploded in the best possible way, and he broke down the actual technique behind it.

“The secret isn’t avoiding patterns—it’s understanding scale,” he said, wearing what I counted as at least four different patterns that somehow looked like they belonged together. “Same scale patterns compete with each other. Different scales create visual hierarchy. So like, thick stripes with tiny polka dots works because your eye knows which one is the star of the show.”

I wrote that down word for word because it was one of those explanations that suddenly made all those crazy runway looks make sense. It’s not random chaos—it’s composed, like music where different instruments are playing different parts but they all work together.

But the rule that’s getting the most dramatic makeover has got to be age-appropriate dressing. I met this woman, Janet, who’s in her sixties and showed up wearing cargo pants, platform sneakers, and a vintage band t-shirt under a blazer. She looked cooler than most people half her age, and when I told her that, she just shrugged.

“Age-appropriate dressing is just code for making women disappear as they get older,” she said matter-of-factly. “I’ve been wearing what I want since the seventies, and I’m not stopping now because some magazine thinks I should be in beige cardigans and sensible shoes. The only thing that’s inappropriate is letting other people control what you wear based on when you were born.”

Her Instagram is full of outfits that would make fashion editors half her age weep with envy, and the comments are mostly women thanking her for showing them it’s okay to dress with personality after forty. Which is depressing that we need permission for that, but also inspiring that she’s giving it.

The whole “no visible underwear” rule has been dying a slow death for years, but I think 2024 might be when it finally gets buried. Visible bra straps aren’t accidents anymore—they’re styling choices. I’ve seen slip dresses worn as actual dresses, not hidden underneath other clothes. What used to be a wardrobe malfunction is now just… fashion.

“The whole concept comes from this idea that women’s bodies need to be hidden and controlled,” explained this lingerie designer I follow on Instagram. “But showing the construction of an outfit—the straps, the layers, how it’s all put together—that’s actually a really thoughtful aesthetic choice. It’s about transparency, not scandal.”

Remember that Coco Chanel quote about taking one accessory off before you leave the house? Yeah, that’s dead too. The coolest women I know are piling it all on—rings on every finger, layered necklaces, multiple earrings, watches with bracelets, sunglasses and hats at the same time. It’s joyful and expressive instead of edited and restrained.

One accessories designer I talked to was wearing so much jewelry I was genuinely concerned about his ability to type, but it all worked together somehow. “That minimalist, less-is-more thing served its purpose,” he said, “but we’re in a different era now. Sometimes more is more, you know? The key isn’t the quantity—it’s making sure everything you put on has intention behind it.”

Maybe the most surprising rule being broken is the one about not overdressing for casual situations. For decades, showing up too dressed up was almost worse than being underdressed. But now I’m seeing people deliberately creating contrast between their outfits and their environment, and it’s actually kind of brilliant.

This music industry person I follow on TikTok regularly posts photos of herself in full evening gowns at dive bars, sequins at coffee shops, feathers at the grocery store. “There’s something powerful about being dramatically overdressed,” she explained in one video. “You’re saying that every moment deserves celebration, that you don’t need anyone’s permission to wear your most beautiful clothes.”

That hit me hard because I have this gorgeous blue silk dress hanging in my closet that I’ve worn exactly once in the past two years. I keep waiting for the “right” occasion to wear it again. But why? Because some internalized rule says fancy clothes need to be rationed? Meanwhile, this woman is out here creating memorable moments out of ordinary Tuesday afternoons.

Even the seasonal shoe rules are getting completely ignored. You know, no white shoes before Memorial Day or after Labor Day? Several people specifically mentioned wearing their whitest shoes in the middle of winter as a deliberate middle finger to that particular bit of nonsense.

“Those rules made sense when we had dirt roads and no modern cleaning products,” one shoe designer told me, while wearing white boots in February. “But now they’re just arbitrary limitations. Winter is actually when I need bright white shoes the most—for the visual contrast against all the gray slush and sad weather. Why would I deny myself that because of some random calendar date?”

The whole “no horizontal stripes if you’re not model-thin” rule seems to be completely dead too, thank god. I talked to this plus-size model whose style is absolutely incredible, and she was wearing the most gorgeous striped sweater that would have made those old-school fashion magazines clutch their pearls.

“The idea that certain patterns are only for certain body types needs to die,” she said bluntly. “Wear the horizontal stripes. Wear the crop tops. Wear whatever they told you would ‘make you look fat’ because guess what? Looking fat isn’t actually a fashion emergency. Living a restricted, joyless life because of body shame? That’s the real tragedy.”

Another interesting shift is happening with outfit repeating, especially on social media. The old rule was never wear the same thing twice where people might see you, but sustainability concerns have flipped that completely. Now the coolest influencers are proudly showing how they rewear and restyle the same pieces.

“Fast fashion trained us to see rewearing as embarrassing,” one slow fashion advocate explained to me. “But actually, wearing something once and never again should be what’s embarrassing. The most stylish people I know have signature pieces they wear constantly, just styled different ways. That shows confidence and creativity, not to mention basic environmental responsibility.”

Even “don’t wear leggings as pants” seems to have finally died. “That was always about policing women’s bodies anyway,” pointed out one activewear designer I talked to. “The real rule should be ‘wear leggings that fit properly and aren’t see-through,’ not whether they count as ‘real pants.’ If men can wear skinny jeans that show everything, why can’t women wear well-made leggings?”

What’s emerging from all this rule-breaking isn’t chaos, though. It’s actually a more thoughtful approach to personal style. The people who are successfully breaking these rules aren’t doing it randomly—they understand why the rules existed in the first place and they’re making informed decisions about which ones still serve a purpose and which ones are just limiting self-expression.

“I know exactly why you’re not supposed to mix silver and gold jewelry,” one stylist told me, while wearing both metals together in a way that looked completely intentional. “I just think it’s an outdated limitation. I’m not breaking the rule because I don’t know it exists—I’m breaking it because I’ve decided it doesn’t work for my aesthetic goals.”

This conscious rule-breaking is showing up in dress codes too. Wedding guest etiquette is getting a major overhaul, with some of those strict color prohibitions being reconsidered. Obviously don’t wear white to someone else’s wedding—that’s just basic respect—but the blanket ban on any white at all? Or black being inappropriate because it’s “funeral attire”? Those are starting to feel pretty outdated.

Office dress codes are evolving too, partly because the pandemic