Style Rules You Should Absolutely Break
We are - in general - not huge fans of style rules.
Rules *can* be a good thing, creating order or a shorthand way to skip to a desired end result. But you have to have context on who invented them and why. Because style is ultimately completely subjective. There is no clear “right” and “wrong” - only what looks and feels good to you.
And so, a rule is only ever useful if you happen to agree with its creator. In other words, you find with critical thinking that a certain rule consistently creates an end result that helps you look and feel better.
But the tricky thing is that these “fashion rules” are so often presented as absolute fact. That if you dare go against them, you’ll be instantly cast out as a style pariah. And this just isn’t the case.
There is also the unavoidable fact that many of these “rules” originated from creators who never even inhabited the 21st century. Why are we insisting that our pocketbook must match our shoes when I’ve never even uttered the word “pocketbook” outside of the context of this outdated “rule”!?
Let’s take a quick tour of some of the fashion rules we think you should break. And do it with pleasure.
5 Style Rules To Break
“Dress to flatter your figure”
Woof. This one frankly deserves an entire article to itself.
In the meantime, let’s just say that style is about so much more than just dressing our bodies towards a certain shape that we've been made to feel is "ideal". I find that prescriptive rules based on your body tend to just perpetuate negative self-judgements and limit creativity.
You might find yourself reacting to this, objecting “But, I just don’t look good in wide leg pants that make my legs look short!” or “I need to have a defined waistline so I don’t look too wide!”. I urge you to examine that feeling more deeply. What has made you feel that your legs need to look long or your waist slim? Why does that look “better” to you?
And, I’m by no means saying that we should completely throw “flattering” to the side and dress only in shapeless sacks for the rest of our lives. But, I think we should all at least be *aware* of what is driving us to dress in a certain way - and therefore, have the ability to selectively choose something different. Instead of being locked into only dressing to make your body look a certain way, to have the freedom to wake up and prioritize an expressive color combination or exaggerated proportion instead.
I’m also not saying that proportions don’t matter at all. They absolutely do. But creating interesting and artful shapes doesn’t necessitate dressing towards a classically “ideal” hourglass. In fact, unlocking yourself from that requirement invites so much more exciting proportion play.
I have personally found it helpful to apply Amy Smilovic’s idea of thinking of dressing your body as creating architecture. Nobody ever said “oh, I just love that building because it just looks so slim”. It’s about lines, curves, and relief. It’s about contrasts between big and small. Thinking like this helps to de-personalize it, and gives space for your eye to adjust to a different shape that you’ve been told your entire life is “unflattering”.
At the end of the day, don’t let anybody tell you what to do with your own body.
“Dress for your age”
It’s simple: good style has no age limit. In fact, it gets better with time!
It’s perfectly okay if some certain styles that just exude youthfulness don’t feel quite right anymore as you get older - but, only because they no longer properly express the maturity and self-assuredness you’ve found with age. Not because they’re simply considered “inappropriate”.
I’ll admit, for example, that pigtails and pleated mini skirts now feel decidedly too “young” for me. I think it’s because they are both things I did actually wear when I was a teen and so I subconsciously relate them to that era, to that “me”. But I’m a very different “me” than I was as a teen, so wearing them no longer feels like a good expression of my inner self.
But does that mean that pigtails and pleated mini skirts are universally wrong for other women in their 30s? No! Definitely not. I’ve seen others wear them in endlessly chic ways that perfectly suit their style.
It can be super helpful to follow style creators that are similar to you in age, just to remind and inspire you to keep breaking this “rule”. There are many great ‘older’ creators out there, but these are just a few of our favorites.
“Follow all the latest trends”
Quite the opposite! In fact, many of the most stylish women are so because they don’t actively follow trends. They develop a signature style and stick to it over time. Sure, they may selectively adopt a few ideas or trends over time - it’s always okay to evolve - but, their style is always recognizably theirs.
Need help developing your own unique personal style? Learn more about the Style Workshop, a free (!) 8-week content series to walk you through step-by-step
“Save your best pieces for special occasions”
I totally understand this impulse because I used to do it myself. When you *finally* find something really special, you want to protect it. To keep it in its original, pristine condition so that you never have to risk parting with it.
But if you’re saving up all your most special, favorite pieces for special occasions…then what are you wearing the rest of the time? Your not-so-favorite, not-special pieces? And yet you question why your day-to-day feels unspecial and unremarkable.
Similar to “you are what you eat”, in many ways you are what you wear. Let’s not spend the bulk of our lives wearing all the stuff that’s just average.
And, this mentality also just, frankly, sucks from a financial optimization point of view. You end up spending the most money on those “special” pieces that you only wear a few times, and then wear a $10 tee from Target until it’s literally falling apart.
Instead, look at your closet as a set of tools that all work together. The goal is to love every single piece (yes, every one!) and for each to serve a purpose in the life you live every day, not just a few special days per year.
This might mean that you actually spend much less on clothing for those special occasions. Instead of buying a $500 dress to wear as a wedding guest, you might rent - or, simply re-wear the same dress you already have. If I’m craving something new for a special occasion like this, I now prefer to invest that same cash in a new bag, piece of jewelry, or pair of shoes, because I’m *much* more likely to be able to re-style and enjoy those items in my day-to-day than a new fancy dress.
Conversely, you might spend more on clothing intended for every day. Instead of the $10 Target tee, would a $80 tee - thick, plushy, and perfectly fitted - bring you more joy? It might sound frivolous at first. But after all, you just saved yourself $500 on a fancy dress that you’ll only wear once or twice, so I think you more than paid for it. See how this works?
And if you’re concerned about “ruining” these nicer clothes by wearing them on the regular, remember that clothes are meant to be worn. They’re meant to take on signs of wear. If all your clothes are always perfectly pristine, it can actually come off a little like a costume. Jake Birkin herself was never fussy about her eponymous Birkin - she beat it up, and that was all part of the je ne sais quois.
“Never wear this with that”
Like: “never wear black and navy together” or “always match your bag, shoes, and belt”. The list here really goes on and on.
But how many times do I need to say it? There are no fashion rules!
Rules like this were created by someone who happened to aesthetically prefer that combination. It was just their preference. And, many people who prefer not to spend too much of their time self-examining their own preferences when it comes to style and just want to be given rules to follow. I get it, it’s simpler! But that’s how these “rules” were passed around to the point of being taken as hard fact.
But for every one of these rules, there are thousands of incredible looks that prove it wrong. See: this super-chic black and navy look over there to the right.
As always, use the rule if it works for you to help create looks you feel good in. But never feel constrained by the rule.
Devon is a co-founder of Indyx and currently leads Growth for the company from San Francisco. She enjoys admiring other people’s gardens and sleeping in with her French Bulldog, Reggie.
