13 Style "Rules" You Should Never Follow

Some may call it anarchy, but there are very few rules we recommend when it comes to style. We find the freedom to try whatever trends, styles, and silhouettes we want to be a much better learning experience in what we do and don’t like. But we also won’t deny that there are plenty of so-called rules historically enforced in media, so consider this a bit of encouragement for you to toss the lamest ones aside.

Below we thought of some of the worst style advice we’ve ever gotten (your shoes and bag should match! less is always more!) to present a few alternatives to these tropes. Of course, feel free to take or leave what feels best—the point is simply not to be encumbered. Getting dressed is much more exciting that way—we promise.

Unless you’re someone who lives for a matchy-matchy moment, try thinking about your outfit holistically and don’t get too tied up in what specific items match or don’t.

Underwear is intended for wearing whenever and however you very well please.

We always considered this such a silly faux pas. Black and brown are both neutral colors, how could they not complement each other?

Thanks to the reigning athleisure trend, sneakers may never be looked at as strictly a functional wardrobe item ever again. And if you’re only wearing them with leggings or workout shorts, you might be missing out on all their other possibilities.

If there’s one thing we know about what’s flattering it’s that no singular definition can sum it up. In case you’re not quite sure what it means to you (showing off your legs, a color that makes you happy, wearing a dress that clings to your frame, or wearing one that doesn’t touch it at all), you might as well explore your options until you find what feels right.

We appreciate Coco Chanel’s minimalist approach, but have you ever tried adding one more piece before heading out the door? It might feel even better.

Shoes deemed “ugly” for their awkward silhouettes, clunky soles, and an obvious preference of comfort above dainty heels or pointy toes are far from a passing fad. On the contrary, some might even call it a lifestyle.

Not every mixed-print look needs to be as bold as clashing animal patterns. Even small pattern clashes (polka dots and dainty florals) or texture mashups (velvet and lace) can yield some of the most interesting outfit results.

Simply put: Don’t let any label trip you up.

Personal budgets aside, we happen to pride ourselves on finding pieces that look so much more expensive than they actually cost.

If you’re looking to cut back on your consumption, look for rare vintage additions to your wardrobe. Or don’t shop at all.

Not a dress-wearing kind of person? Never a problem.

This past year, when the red carpets of award season were filled with political-statement-making ensembles, it was a reminder of how powerful our clothing choices can be. “Who are you wearing?” might be the most typical fashion question, but it’s also a valid one that can open a deeper conversation about not only what we wear but why it matters. For example, the designers below are also advocates for issues including women’s rights and environmental sustainability.

Up next, take a look at the fashion trends Who What Wear readers refuse to wear.