You’ve heard these all before: Every woman should own these 10 items. You shouldn’t wear white after Labor Day. You shouldn’t spend so much on your appearance. You should dress for your body, your age, your coloring.
Fashion dos and don’ts are ubiquitous. Everyone from beauty editors to your best friend has a strong opinion on what you should and shouldn’t wear — and they aren’t afraid to share it with you, unsolicited.
We’re offered quizzes that analyze our body types and then dole out judge-y instructions about what we can and can’t do as a result. Some prefer to scare us into conformity, posting embarrassing photos and horrifying tales of what happens when you refuse to heed their warning and dress accordingly. Still others use the inverse tactic, featuring airbrushed photos of genetically perfect beings, with step-by-step instructions for how to carve your image into a near-replica (spoiler alert: it never works).
Instead of obsessively trying to follow these rules, give yourself permission to ignore them and have a little fun while still being work appropriate. Here’s how.
1. Think about why the directive is being offered in the first place.
Many fashion shoulds are relatively arbitrary — they assume each body, office, and personal goal is uniform. This means you need to interrogate the rule before you embrace it. Does its justification align with your lifestyle and personal ethos? Does it fit the expectations in your office? Only you know the circumstances of your life and can accurately determine what is and isn’t applicable.
For instance, in some more conservative offices, women are often told they shouldn’t wear open-toed shoes. That, of course, does not apply to all offices, particularly more creative ones. When in doubt, take your lead from the highest-ranking woman in your office and pay attention to how your clients dress — that is often your winning combination.
2. Be realistic about how and when you can effectively subvert the rule.
There may not be absolute shoulds and should-nots, but there are certainly good and bad times and places for stepping outside the visual boundaries. Everything from wearing a bold pattern or color to exposing some skin demands discretion — not because it’s inherently wrong or right, but because it’s more effective in some contexts than others.
Calculated risk is key for success, as is knowing your audience. And if what you really want to wear will hinder your ability to flourish in a particular context, then it’s up to you to gauge which is more important in that moment and in the long run.
For example, if you’re interviewing for a job at a New York investment bank, a hot pink Hawaiian-print dress might not be the most appropriate option. Could it work and make you stand out in a sea of black pants? Sure — or it might backfire. But that doesn’t mean you have to wear something boring and subdued. Find a happy medium, maybe with a colorful scarf or red shoes.
3. Create your own rules.
Your fashion rules should support your personal goals — and only you know what those are. So when in doubt, rewrite the rules to work toward what you’re trying to achieve. Perhaps you’re on the petite side, so always wearing heels helps to put you eye-level with your counterparts — and that’s more valuable to you than some added comfort. Or maybe you want to simplify your style and your life, so you forgo some variety in favor of consistency and peace of mind. Whatever your personal and professional aspirations, align your image accordingly.
4. Whatever choice you make, own it.
Confidence is more than half the equation when it comes to determining the success or failure or any particular look.
Even if you follow those guidelines, you may occasionally regret bucking the rulebook and decide that, in fact, maybe you shouldn’t wear something — not because “they” say you shouldn’t, but because you don’t feel your best in it. That’s the underlying metric for whether any single should or should-not makes it onto your list: How does it make you feel?
You can also pay attention to how a particular piece was received — but only from certain audiences. A coworker who says, “You should be dyeing your hair. I don’t like a woman with grays” should be promptly ignored, but you should listen if your HR rep says your crop top violates the dress code. No one wants to be formally reprimanded or even receive disapproving glares any more than we want to feel physical discomfort. And when you know you look great, you feel great — and that resonates with everyone around you. Weigh the combination of the physical sensation, your personal self-perception, and the response from those around you to figure out your best looks.
Whatever makes it to your “do not wear” list should be a result of your own thoughtful consideration and reflection on whether it enhances or detracts from the best version of you — not some impersonal list of bossy rules.
Anna Akbari, Ph.D. is a sociologist, entrepreneur, and the "thinking person's stylist." She is the founder of Sociology of Style, which takes an intelligent approach to image and offers holistic image consulting and life coaching services. Find out more and follow her on Twitter.