7 Times Breaking Fashion Rules Led To Something Pretty Magical

When thinking of breaking fashion rules, the majority of us might think of train-wreck moments. But really it can lead to some pretty magical outcomes — it just takes a skilled eye and patience to pull it off. Style isn't just about playing with clothes in front of your mirror, or throwing flippy dresses over your head and pulling on soft-as-buttah leather booties on your feet. At times, it can be downright stressful. Just think of all those times you stood in your underwear in front of your closet and came to the slow and galling realization you have nothing to wear. Or how about those times you did have an outfit in mind, but once you zipped it up it looked like a circus on you? Better on paper... and now you're 15 minutes late. 

Just like with any love affair there are some tough times in our relationship with style. But it can be even harder — and more intimidating — if you're just starting out. What are the rules? How do you piece clothes together? Does this look good or just crazytown? And when you have a heavy rule book hovering over your head in the form of the September issue, it can get even more confusing. Which way is the right way?

But the cool thing is, you're actually the most stylish when you're not stylish at all. Sure the fashion world likes to throw rules our way on what works and what looks good and what doesn't, but I have a sneaking feeling that they do that just so they can have the pleasure of breaking those rules in the next breath. Below are seven trends that prove breaking fashion rules leads to some magic and inspired trends. Why? Because fashion isn't about rules; it's about expression, and people appreciate it most when you run wild with your aesthetic.

1. The Granny Chic Trend

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Cocoon coats that look like you're wearing your grandfather's church coat, chunky sweaters that skim your thighs, midi skirts, ladylike little handbags, pleated pants, and chunky block heels with frilly socks — everything about this trend sounds like it shouldn't work together, but it really, really does. It goes against everything that we learned was correct: It's baggy, kitschy, and reminiscent of your grandmother's curtains, but that's what makes it so darn charming. It's a take on the girly style, but then matures it so it looks like the lot of us are excited to grow old rather than fear it. So put away the wrinkle cream ladies, there's nothing but bright skies ahead of us.

2. The Ugly-Pretty Trend

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You've probably dabbled in this trend even if you haven't realized it, that's how big it was this year. For example, did you buy a pair of clunky sandals this year? Do you have Birkenstocks in your closet or a fanny pack stowed away on your purse shelf? You might have cracked and discreetly bought a pair of mom jeans, or have a grandpa sweater that Macklemore himself would be proud of. These are all things that the fashion community have scoffed at previously, and would have dubbed you as a social pariah if you had tried and worn it out. So what changed? 

Nothing — it's just fun to go against the grain. The majority of these pieces are so ugly that they're amazing when paired with higher quality, more high-fashion pieces. For example, orthopedic-like shoes are paired with feminine, luxe looking dresses; mom jeans are matched with sleek leather jackets and sharp boots; fanny-packs are cinched around tailored pants and classic shirts. Contrasts are fun, and the fashion world tips its hat to those that are able to take something no one wants and make it into something fabulous.

3. The Sweatpants Trend

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Quite possibly the most exciting trend to ever have been created: We now have gotten permission to step outside of our houses with the same sweats we've been watching Bob's Burgers marathons in. What crafty genius snuck that one past Vogue? All a girl has to do is put on heels or pair those sweats with a tailored, classic top and she's golden. And what's so fun about this look is that it's a challenge to make it look classy. You can experiment with dangly earrings, see how it feels when paired with a blazer or your most professor-y bluchers. It's like solving a puzzle and it gets your creative thoughts going. See? Do what you want; there are no rules in this land.

4. The "Pajamas As Formal-Wear" Trend

Even more mind-blowing than the sweatpants trend, this time around fashionistas took it a step further and decided PJs were now totally OK to be worn to fancy dinners and gala fundraisers. All you have to do is put diamonds at your ears, strappy heels at your feet, and maybe add some glitter to your clutch, and your silk jammies are every inch as appropriate as a taffeta ballgown. 

Honestly, this is a pretty fabulous look. You're wearing head to toe silk, the flimsy lines of the "suit" accent the feminine lines of your body, and you get to play with the challenge of keeping it fancy rather than time-to-hit-the-sheets-y. It's an amazing dare, and it encourages people to look at their closets differently. Because if pajamas can pass as formal-wear, what else can you work into a new formula?

5. The Androgynous Trend

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Women have their own clothes, and men have their own clothes. Right? Not quite. While it's fun to put on a twirly dress now and again, there's been a movement that would allow you to nip into your brother's closet and steal his shirts and he into yours to steal your pants. The lines are becoming murky, and that in itself is pretty magic. Why? Because you don't have to worry about having your gender define you. Good clothes that make you happy are good clothes that make you happy. If you want a chance to play with fashion without having to stress your femininity, then you don't have to. These days, it's every inch as stylish to appear in a tuxedo jacket and bluchers as in a swirly skirt and heels. Sometimes even more so.

6. The Normcore Trend

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This trend is like the antichrist of fashion. And that's why everyone went wild over it. Where fashion is made out to be something wonderfully frivolous and full of fun and complex steps, normcore wiped that idea away and created an army of Jerry Seinfelds instead. It took everything we thought good style was and flipped it on its head. And the thing is, a lot of us loved it. Who ever thought there would be a day where we would think looking like our parents in Disney World circa 1994 would be all sorts of stylish? But here we are.

Gap ran with it especially, and their Fall 2014 slogans summarized the intention of the fashion world's tongue-in-cheek introduction of the trend: "Simple clothes. For you to complicate." Meaning, take this piece and do what you want with it. It'll look fabulous because it's you, not because we gave you rules on how to dress it.

7. The '90s Revival Trend

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Arguably the least stylish era in our history books, what does it say that we went out of our way to revive the slip dresses and slouchy beanies of our youth? According to fashion writer Hadley Freeman from The Guardian"You see, the divide isn't between good and bad fashion — it's between fashion and no fashion, and whereas, the '80s definitely had fashion, the '90s had none." 

So why would we want to resuscitate a whole decade that's left its trendsetters uninspired? Because it's a challenge, and the fashion world loves being challenged. Think of how it's being revived 25 years later: We're wrapping plaid shirts over sleek, minimalist dresses; popping slips over unexpected cotton tees; lace-up tops with crisp blazers; juxtaposing beanies with feminine dresses. We've brought back those trends, but we worked them with our unique aesthetic. And that's exactly why it's considered so on-trend now: It's because it's our way. And even though the fashion world throws a heavy law book at you every September with dos and don'ts, it's most proud of you when you nudge it aside and make your clothes yours. 

Images: Eugenio Marongiu/Fotolia

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