It was a mid-winter evening in 1992, my senior year in high school. I remember this moment so vividly because I owned this buffalo plaid boyfriend coat that I loved and because it was the first evening since getting my driver’s license that my parents allowed me to drive at night. Back then, restrictions on the licenses for new teen drivers, like driving after dark, didn’t exist because that would have been like closing the barn doors after the horses got out. Gen X kids already survived asphalt playgrounds, our parents’ second-hand smoke, our photos not making it onto milk cartons, and being latchkey kids. Clearly, we were invincible. But my parents were cautious and didn’t immediately let me take the car out without supervision after the sun went down. But on this night, they finally did.

So on that crisp winter evening in 1992, I was given the keys to one of the family cars. I put on that buffalo plaid coat and for the first time drove to a nearby party that was less than 10 blocks away. But it didn’t matter, I felt independent and as if at that moment my world became much more expansive. The car had a tape deck where the tape sitting in the deck would automatically play upon ignition of the car, and a popular release the year before, Red Hot + Blue, a Tribute to Cole Porter, was in the tape deck ready to go. The tape, which played on heavy rotation in my mom’s car, is named after Cole Porter’s musical, Red, Hot + Blue, and is a compilation release to benefit AIDS research and relief— an epidemic which was raging in ’92— from the Red Hot + Blue series featuring contemporary pop performers reinterpreting several of Cole Porter’s songs. To this day, I still love that album. In what couldn’t have been a more perfect moment, the song from the album that played as I took my first moonlit drive on that cold winter night was track number 8, Don’t Fence Me In, performed by David Byrne. I grinned widely as I drove alone at night for the first time in my life.


That moment wasn’t just perfect because the song so aptly captured me claiming a moment of freedom as a teen, it also captured who I am and have always been as a person. I don’t like rules, I don’t like feeling limited and I don’t like boundaries. I’m not commitment-phobic, but in all things I commit to, I need to know there is always an escape route. I thrive when I feel free and open as if my world is like a wide, vast open plane where the horizon line can be seen in the distance without obstructions cluttering the view. I am also extremely averse to being told what to do, so much so that even if I have an inclination towards doing something, the second someone has a response to my desire along the lines of, “yes, you really should be doing that,” I don’t want to do it any longer. Limitation gives me a physical sensation in my body that feels like suffocation. I need sprawl, I need to run, I need to expand, I need a fenceless life, and I need to know that the horizon line in the distance will always be there. For me, this isn’t just my safety, this is also from where the essence of my creativity originates. I read recently about something called Control Aversion which, not surprisingly, many entrepreneurs have. No surprise that I wound up running my own business.

It’s not as if I got bad marks for not playing well with others or not being a good team player. I am not some sort of anarchist who fights with police officers or argues with the rule of law. Sure, if I have an issue with a rule, my patience will be fleeting and I might quit and walk away, but I am a law-abiding citizen without so much as a traffic violation and who has a very collaborative spirit. All I need, basically, is sprawl, freedom, and to not feel like I am being suffocated by someone else’s version of who I am supposed to be or what I am supposed to do. Otherwise, I’ll leave you alone if you leave me alone. It’s quite simple.


So why am I sharing this disclosure of my inner psyche that clearly needs more time on a therapist’s couch? Well, as you can probably imagine, fashion rules drive me absolutely crazy. It’s not so much the rules that bug me, it’s the rigidness in which some women adhere to them that does. The way I see it, instead of being liberated by these rules, some women will willingly choose to be fenced in, dictated to, and will give up control of their wardrobes for the sake of being told what to wear and buy, and I know this isn’t what women want. In fact, women seek out fashion rules to be empowered, liberated, and so they can expand their wardrobes, not limit them. Therefore, my beef isn’t so much with the fashion rules themselves, it’s the nature of how they often get applied. Fashion rules can be helpful tools. I wrote a whole book that contained hundreds of pages of rules. I would be a hypocrite and a terrible opportunist if I said they weren’t helpful.

I see the rigidness of how women apply fashion rules all the time. I once worked with a client who took my guideline for the size of earrings to be no larger than an eye socket when not wanting them to be distracting so seriously that from that point on, she placed every single pair of earrings at a store against her eye socket when determining if she should buy them. If they weren’t perfect she left them at the store. I have met women who after learning which colors work best for them, wouldn’t stray beyond their color wheel even if someone was threatening their lives if they didn’t try on a sweater in an unflattering color. There are petite women who will never wear cropped pants, women with large chests who haven’t worn crew necks in decades, and women who follow every single fashion rule like it was handed down by God himself. As a control-averse person, it, admittedly, drives me insane.


Fashion rules can be huge eye-openers. They can provide answers to burning fashion questions that plague women and their closets. In a time when most women feel overwhelmed, where stores are over-saturated, and fashion advice can regularly come at women like speeding cars on the freeway, fashion rules can provide helpful guidance to sort through it all. What I also realize is that the average woman navigating the endless amount of merchandise has no formative fashion training and, for the most part, is winging it. For her, these fashion rules can be like buoys to cling to. Therefore, for me, who does have 30 years of industry experience, coming in with what seems like judgment towards women for relying on these rules definitely seems thoughtless, insensitive, arrogant, and smug. So trust me when I say, I am not asking you to throw the fashion rules you have to come to rely on out the window, nor am I judging you for using them. I am, however, suggesting a different approach to following so you can build a more empowered and less rigid relationship to using them


As I said in my book, fashion rules should be seen as guidance or guideposts that allow you to make informed choices. There is a great quote by Charlie Parker that I love, “Master your instrument, Master the music. And then forget all that bullshit and just play.” This is what I mean by making informed choices. Fashion guidelines are meant to be empowering, not limiting, they’re meant to give you that same feeling of wide open sprawl I was describing on that winter night I got the keys to my parent’s car. They’re meant to make you feel in control, not oppressed, restricted, or controlled. They’re not meant to fence you in. Why would you then want to shackle yourself to fashion rules once you’ve finally been liberated by them?

The difference between making informed choices through knowing fashion rules and rigidly following fashion rules is that informed choices give you the power to decide for yourself based on the information you possess, just as Charlie Parker took all his knowledge and musical training, got on stage, and played. Without the rules, training, and knowledge of the fundamentals of music and his instrument, Parker wouldn’t have been in control, he would have just produced untrained noise. Yet, had Charlie Parker followed all his training rigidly, to the letter, never allowing himself to knowledgeably explore, he wouldn’t have been in control, the rules would have controlled him, and he likely never would have become one of the greatest musical innovators of the 20th century. The same is true for you and fashion rules. Without knowing the fashion rules, you’re just winging it or making noise. If you rigidly follow the fashion rules you’re just doing the same as playing the music on a sheet — the rules are controlling all of your decisions; it’s fine, but not exactly liberating. However by using a mastery of fashion rules, the same as Charlie Parker did, you’re not winging it, you’re using the rules you’ve acquired to be in control.

To help you better understand this, I will give you two different scenarios.


Woman A

Woman A gets dressed and likes her outfit today but has no idea what about it is working but wishes she did because she’d love to have more successful days putting good outfits together. The next day Woman A gets dressed again and feels like something about her outfit is wrong. She has no idea what the problem is so she can’t avoid this mistake in the future.

Essentially, Woman A is throwing spaghetti against the wall with the hopes that something will stick. Woman A is not in control.

To get control of her wardrobe, Woman A reads and acquires fashion knowledge wherever she can get it. She reads books and blogs despite the fact that the information out there is confusing, sometimes contradictory, and maybe even questionable. Woman A is a good student following every rule closely. She keeps going because, clearly, this will give her control over her wardrobe. More rules, more control, is what Woman A assuredly thinks. Yet, the more Woman A reads, the narrower Woman A’s options get in terms of what she can wear, the colors she can select from, and the pant shapes she can buy because Woman A has analyzed every square inch of her body has kept reading, has kept amassing knowledge, thinking and playing by the rules. The more rules, the smaller the scope of options. Woman A reads that skinny jeans are out, she starts to worry she needs to get rid of all her pants.

Woman A is still not in control.

Woman B

Woman B gets dressed and is in the same predicament as Woman A. She’s also throwing spaghetti against the wall and decides to do something about it.

Woman B also amasses knowledge of different fashion rules and uses them to help her situationally make decisions or informed choices. Despite having learned that cropped pants may not be the best choice for her now, Woman B buys and happily wears them anyway, only this time instead of not knowing what cropped pants do to her legs. she wears anyway with full knowledge of the consequences of her choice. Maybe Woman B will use other tips to make her legs look longer when wearing these pants, maybe she won’t. Woman B has the power to decide vs. before she amassed the knowledge she has now and didn’t know one way or another. When it’s time to give a lecture or get on Zoom, Woman B will choose to not wear her optic black and white top because she will understand that in these public speaking or interfacing situations, a bold black and white top will pull focus from her face and message. Prior to learning this fact about black and white prints, Woman B often wore these bold prints to speak and wondered why she had to work so hard to be heard. But now she knows, and instead of getting rid of these bold optic tops that she enjoys wearing entirely, Woman B chooses to only wear them when she isn’t publicly speaking or when people don’t need to focus on what she is communicating. In times when she won’t be in situations like this, she will enjoy wearing them. Woman B has taken the fashion rules she has learned and chosen to powerfully apply them in ways that work for her.

Woman B is in control.

Can you see the distinction? Woman A allowed the fashion rules to run her wardrobe while Woman B, equally knowledgeable in the rules, used them to decide for herself. Both women amassed knowledge but chose to apply what they learned differently. In learning the rules, Woman B became empowered and liberated. She mastered her instrument and can now play, just like Charlie Parker. Woman A may know things but she still isn’t calling the shots.


This is not to say we all have to be like Charlier Parker. Are you more like Woman A and it’s working? Well, don’t let me get in the way of that. There are people out there who can be very much more compliant and empowered by clear-cut, decisive rules. If it works, it works. There is no need to throw another rule onto the pile or force yourself to be how you naturally aren’t. Yet, despite where you sit on the spectrum, fashion rules aren’t dictum, they’re guidelines and tools that are meant to answer all those burning whys of fashion that have plagued you. How strongly or flexibly you apply them is for you to decide. Whether you follow these guidelines you have amassed closely and to the letter, use them to make informed choices, or don’t use them at all, this is your call. What does matter is that you feel free and not controlled. Another thing that is critical is that you consider the sources from which these rules originate.


I say this without even a hint of a suggestion that all other fashion blogs other than mine can’t offer you wise, helpful fashion guidance because there is plenty of helpful advice out there from all different sources. But, please, always consider your sources of these rules before you blindly build your wardrobe around them. I love a new fashion theory or interesting approach to styling but few fashion rules are road-tested or come from any experience.

Here’s what I know. Fashion bloggers who share fashion rules need content. Coming up with fresh content ideas is hard. Unless you consider a passion for fashion experience, the average fashion blogger has little to none. Many fashion bloggers also speak from personal experience, which can be fine but limited to their own views, opinions, and personal physical characteristics. Certainly, they mean well, but many fashion bloggers lack the expansive test pool of subjects to float fashion rules and make them universal. In terms of fashion rules not originated by a blogger, many of the fashion rules they share on their blogs are just regurgitated folklore or advice that is too generic, misinterpreted, inaccurate, poorly explained, or plain content filler. In desperation for any guidance, women will take much of this knowledge at face value without questioning the accuracy because, oftentimes, women tend towards not trusting themselves with fashion.

Obviously, this can get confusing because you want answers to your fashion questions, but how are you supposed to distill all these rules floating around and know what is and isn’t true? Who can you trust? You trust yourself. Your instinct will always tell you something isn’t useful. You never needed fashion rules in the first place to tell that you had an issue with an outfit or item in your closet. You already knew the problems existed. They were what sent you on a journey looking for answers in the first place. Fashion rules are simply meant to help you knowledgeably repeat successes and avoid failures by empowering you with the knowledge to make decisions for yourself. Therefore, when you apply a fashion rule and notice it doesn’t help, doesn’t make a difference, or, worse, doesn’t make your wardrobe feel expansive, freed, or liberated, you can let it go. Always apply a fashion rule because it works, not because you feel you have to. Don’t let fashion rules run your wardrobe.

As the late, great Cole Porter wrote in his song, “Don’t Fence Me In”, and as the Amazing Charlie Parker believed, you master your instrument, forget all that bullshit and just play. Fashion rules aren’t meant to control you, they are meant to put you in control.

Now get out there and play.