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29 Outfits That Break Fashion's Most Annoying "Rules"

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If we published a book that contained every single "fashion rule" we've ever been told to follow, well, it'd likely be the size of an encyclopedia. And once we accounted for color-coordination, styling tips, or "flattering your figure" (sigh), this how-to-dress rulebook would essentially leave us with nothing but black A-line dresses to wear. And where's the fun in that?

No one (and we mean no one) knows how to ditch, disobey, and totally ignore said "rules" like street style stars. They take the pieces so many would refuse to wear, that so many would dub "unflattering," that so many could never even understand why something that crazy would ever even be produced (let alone bought), and turn them on their heads. They prove that even the most wild of items have potential, all you need is a little creativity and a whole lot of confidence. Sure, some may call it peacocking and vying for attention. We call it playing the game by your own rules.

The 29 women ahead are pros at doing just that. Click on to see how good creating your own style looks.

September is typically a time when fashion publications definitively tell you what’s in, and what’s out. Fuck that . We’re dedicating the next couple of weeks to celebrate all the iconoclasts, independent thinkers, and individuals with unique personal styles who’d rather say Fuck The Fashion Rules than follow them.

We've all been told not to "hide our figure," but sometimes, it makes a killer statement to do just that.

Photographed by Victoria Adamson.

Play with boxy silhouettes, because, why not?

Photographed by Victoria Adamson.

Skip the hemming and let your pants graze the ground. Yet another product of the Vetements effect.

Photographed by Victoria Adamson.

If you think a suit has to be paired with a dress shoe, think again — and consider a pair of Converse.

Photographed by Victoria Adamson.

You've probably heard boyfriend jeans aren't "flattering," but with a bright sweater, oversized jacket, and heeled booties, there's nothing wrong with this look.

Photographed by Victoria Adamson.

Horizontal stripes are pretty damn great, no?

Photographed by Victoria Adamson.

Oh no! Not some "excess fabric"!

Photographed by Victoria Adamson.

Don't let anyone tell you that too many layers will make you look bulky (like it's a bad thing).

Photographed by Victoria Adamson.

Instead of hemming your jeans, go for a rule-breaking oversized cuff.

Photographed by Victoria Adamson.

Skinny jeans are never the only option.

Photographed by Victoria Adamson.

A shirt should be tucked nicely into a skirt, and never show at the bottom. Right? Wrong.

Photographed by Victoria Adamson.

Some say not to wear colors that are too close to each other on the color wheel. We say monochromatic looks are all the rage.

Photographed by Victoria Adamson.

Let those sleeves hang low, girl.

Photographed by Victoria Adamson.

High boots + short dress? Not here.

Photographed by Victoria Adamson.

Bring on the volume.

Photographed by Victoria Adamson.

Wearing your clothes the way they're "supposed" to be worn is SO two years ago. Tug that button-up shirt off your shoulder. Hey, put it on backward if you want.

Photographed by Victoria Adamson.

We've already said brown shouldn't be knocked as a non-fashion color. This outfit reinforces that notion.

Photographed by Victoria Adamson.

No bra? No problem.

Photographed by Victoria Adamson.

You can wear tulle without looking like you're en route to dance class.

Photographed by Victoria Adamson.

Match your bag to your shoes? Um, no thanks.

Photographed by Victoria Adamson.

Go on, let that belly button breathe.

Photographed by Victoria Adamson.

Here's some model-off-duty proof that ripped tights don't have to get thrown straight into the trash.

Photographed by Victoria Adamson.

Sequins aren't reserved for nighttime events — with an athletic sneaker and graphic tee, they're fair game for daytime, too.

Photographed by Victoria Adamson.

Though this is actually a jumpsuit, layering a bra top over a shirt is one of our favorite styling tricks.

Photographed by Victoria Adamson.

Forget sending your clothes to the tailor. This look is about ill-fitting, all the way.

Photographed by Victoria Adamson.

Been told not to accentuate your hips? Guess what: Many silhouettes today do just that — and look how good it looks.

Photographed by Victoria Adamson.

In fact, the same goes for shoulder accentuation.

Photographed by Victoria Adamson.

Have you been trained to let just one print do the talking? We dare you to try clashing patterns and see how great it feels.

Photographed by Victoria Adamson.

If you ask us, unique vintage finds are so much cooler than all-designer-everything.

Photographed by Victoria Adamson.

Like what you see? How about some more R29 goodness, right here?

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