To paraphrase makeup artist and YouTuber Robert Welsh there are no “rules” to getting dressed…but there is a theory. And, as with any form of creative expression, it is important to learn that theory in order to properly subvert it; that is, to know the mold before you break the mold.
Things like proportions, fabrics, and fit are all important to pay attention to when you’re building a look, but, beyond that, most of the fashion rules that we’ve been taught have been passed down through generations of women who weren’t always encouraged or able to express themselves. These days, though, self-expression is not only allowed, it’s downright necessary. I’m gonna tell you why some well-known fashion rules exist, and exactly how you can break them.
1. The Little Black Dress
Coming to prominence in the late 1920s and through the Great Depression, the LBD became a favorite of women of all classes and backgrounds due to its affordability and simple elegance. A 1926 Vogue editorial featuring Coco Chanel’s short, understated version—referred to as a “uniform for women of taste,”—is largely considered one of the first to successfully position black—the color—as the chic choice for women of means and style, rather than simply what you wore after your husband died of dysentery.
The popularity of the little black dress was bolstered by Technicolor films and their starlets, as other colors would scramble the coloring process, but it wouldn’t become truly ubiquitous until Audrey Hepburn wore her now iconic Givenchy gown in Breakfast at Tiffany’s.
These days, in my opinion, there’s simply too much choice (and too many other people out there following the rules) to limit your freakum and formal dresses to just black. That’s not to say I think black is bland (quite the opposite) but, think about it: when has anyone ever been the only one wearing black at a party?
In episode one of the True Style podcast, I said:
Most of the time, the formal events in our lives are something we’d love to look back on. This is why I stress making sure you’re dressing like yourself, and injecting your own style into your fancy clothes.
To me, every time you leave the house is a chance to express who you are, so, if you’re in the market for a new go-to, here’s some slightly unconventional but still versatile options:
That said, if you enjoy wearing black, enjoy the simplicity and ease, and already own a perfectly good LBD: wear it! The point of this article—and everything I do—is not to tell you what to do, but to show you what you can do.
2. “Basics Every Woman Should Have!”
Speaking of garments every woman is encouraged—no, expected—to have and wear in her daily life, the little black dress is often just one of an arbitrary list of 10-20 items in articles like the ones below that seem to be a great way to meet a deadline and fill up pages in a magazine but serve absolutely no other purpose when it comes to finding your personal style.
In Capsule Wardrobes: Do They Work?, I warned:
…you should be cautious of any super-generalized fashion advice that lacks nuance relevant to your life.
…And these articles are exactly what I’m talking about. They’re a good place to look for ideas if you’re building a wardrobe from scratch, but no one can tell you what you absolutely 100% need and “can’t function without” without knowing, you know, how you function. That means your lifestyle, your environment, your workplace, your preferences and, of course, your tastes.
Rather than using these write-ups as a checklist for your wardrobe, create your own checklist by looking at what you’re inspired by, what you already have, and what you need to bring it all together.
3. The Myth of “Flattering”
If you never learn another fact about me and the way I approach clothing, let it be this: I hate body typing. All of it, from fruit-based ones to the Kibbe system to whichever new one comes along in a few years to tell us what kind of jeans we need to buy.
Rather than trying to force ourselves into categories based on what someone else thinks should work for us, I always stress the importance of figuring out what you like. Instead of body types: body goals.
Most advice based on your physical form alone will encourage you to shrink and hide your “flaws,” such as your wide hips, your large chest, your soft tummy. Focusing instead on what you want your body to look like and what you want to emphasize will guarantee that you not only honor your style but also yourself, and, of course, free your mind from the manufactured discontent that the fashion industry utilizes in order to turn us into mindless consumers.
And, for the record, it’s okay to be positively neutral or even occasionally self-conscious about your body or parts of it. None of us are exempt from the pressures of society. I hate my arms, I don’t show off my leg scars if I can help it: but in what you choose to conceal, remember there’s so much more of you that’s worth showing off however you want to do so. Even if that means investing in things like shapewear.
In “It’s Not You, It’s The Clothes: Size and Fit,” I said:
In a world where most of us can’t afford to get clothes made to our exact size and shape, shape wear isn’t about changing your body or even really “slimming you out”. It’s meant to redistribute your curves and make your garment more comfortable and body skimming rather than restrictive and smothering.
At the end of the day, I can’t tell you how to feel about your body. But you shouldn’t let anyone else tell you how to feel about your body, either. If you want to show off the things that fashion has deemed “flawed,” do it. If you’re working on growing your confidence and want to shield yourself from critical eyes while you do that, that’s absolutely fine, too.
4. and 5. No White After Labor Day/No Black In The Summer
I promise, the sole point of this article is not to promote the many times I’ve been correct on my forgotten podcast. But, just to quote myself one last time:
No white after Labor Day became one of dozens, maybe hundreds of rules meant to separate the initiated from the uninitiated, the elite from the commoners. Everything from the length of sleeve one wore to the opera to daily schedules that demanded different outfits for different times of day were used to spot those who simply weren’t good enough to hobknob with the aristocracy. By the 1930s, dark colors had become the standard for regular city folk. Therefore, white became the look of leisure. White meant you didn’t have to work, lest you risk getting your perfect linen suit dirty. It meant you could afford to summer in the Hamptons away from the urban grime. The rule trickled down to the middle class via the fashion magazines of the 50s, and soon, regular women accepted that white was simply for the summer.
-From “Seasonal Transitions and White After Labor Day”
So, whether you’re “allowed” to wear white after Labor Day (or black in the summer), historically, has nothing to do with the colors themselves and everything to do with an outdated form of elitism.
But, wait, doesn’t white actually reflect heat and black absorb it? Yes, but what it really comes down to is fabrics.
Wearing a white linen dress in the dead of winter simply makes no sense, and neither does wearing black wool pants in 100 degree weather, but, a white wool pant makes perfect sense in the snow, and your linen dress can come in black and still keep you cool. Natural plant-based fibers like cotton, the aforementioned linen and even rayon (created from plant cellulose) allow air to flow through their weaves and keep you cool, whereas any material made from animal hairs or skin, and all synthetic polyester fabrics trap heat. Check those garment tags!
6. No Print Mixing
People who are against mixing prints are boring. There, I said it. Even if you're not into the idea of piling stripes on with plaid and polka dots, you can’t deny that, at the very least, leopard is a neutral.
Of course, I’ve written a guide on how to mix patterns (aka, How to Clash Without Crashing), at beginner, intermediate and advanced levels so you know how I feel on the topic.
7. No Mixing Metals
I’ll admit, it took me a hot minute to get on the mixing metals wave, but now that I’m here, I can’t believe it took me so long. Of course, the trick to pulling it off—like any other “unconventional” styling—is to make it look intentional.
From Accessorizing 101:
The easiest way to mix silver and gold jewelry (or yellow gold + rose gold, or even silver + gunmetal) is to wear one of each metal in the same type. So, for example, at least two bracelets: one silver and one gold, so that any additional piece you put on matches another.
Basically, when in doubt, just keep adding things until it feels right. Which, speaking of piling things on:
8. “Take one thing off before you leave the house!”
Do I even need to explain why I hate this “advice?” Whether you’re a minimalist or maximalist at heart, it’s up to you to decide how much is too much and how much is just enough. Funnily enough, I see this little rule leveraged the most toward older women…
9. ANY Age-Based Advice
As I rapidly approach my thirties, there seems to be a new limitation imposed on me everyday, and that feeling of being boxed in only gets worse for women as we age.
While I have certainly been one to call out grown women for still shopping in the Juniors department (hint: sizes that are odd-numbered are meant for pubescent bodies), so long as we’re all buying clothes that fit, who cares who it’s “for?” Imagine if I were to listen to the mantra that “if you were around for the trend the first time, you’re too old for it now.” I’d never have finally gotten my dream denim patchwork ankle boots. And that would be a crime.
10. “Your Colors”
There’s been more than a few TikTok trends and hundreds, if not thousands of magazine articles meant to help women figure out if they’re a “winter” or a “spring” or, as I like to call it here in LA, an “awards season” or a “pilot season.”
Maybe it’s because I was blessed with melanin so pretty much any color looks good on me (clothing wise…don’t put me in any makeup with yellow undertones, though), but, I say it’s all a bunch of baloney.
The best colors—and in fact, the best garment, the best silhouette, the best jewelry, and anything else— for you are the ones you feel the happiest and most confident in. Period.
The Only “Rule” You Should Follow
Every outfit you’ve ever seen that “works,” does so because of four things:
Fit
Proportion
Texture
Details
With honorable mention going to: Intention.
As long as everything you put on comes together in harmony, nothing else matters.
