How to Develop Your Personal Style and Fashion Philosophy

These days it can be a challenge to find your personal style when you are bombarded with so much noise online. Someone is always trying to sell you something whether its via the incessant marketing from the fashion industry or the abundance of influencers trying to dictate what is it isn’t cool. The trend cycles move so fast now that it is too easy to get swept up in them. I know I have. It has taken me some practice, and a lot of bad spending choices, to build a discerning eye when it comes to fashion. I am still on my personal style journey, but I am better now at knowing if an item fits with my style or if I’m just drawn of the flashy-ness of the marketing tactics. 

For someone who has always been into fashion, I surprise myself with some of the bad choices that I’ve made over the years when it comes to spending money on clothes that don’t actually fit my personal style. But what is my personal style? I have been spending more time to discover it, and to create a vision for my wardrobe. I like shiny new things and get easily distracted by trends. I’ve blown a lot of my money on cluttering my closet that items that aren’t super cohesive. My goal is to make better shopping decisions that are more in line with my personal style, and build my dream wardrobe. I have been overhauling my closet for the past few years.

Fran Fine Outfit Inspiration with a Fabulous 90s Franco Moschino Blazer

Feeling proud of my “The Nanny” inspired outfit with a vintage Moschino blazer from an early 90’s Franco Moschino collection

Lessons from The Nanny

Recently I have been obsessed with Fran Fine’s style on The Nanny and the costume designer on the show, Brenda Cooper. As I rewatched the show I noticed that a lot of Fran’s signature style items were the same things that I love - bright colors, bold patterns, statement blazers and blouses, and metallics. I took a lot of notes on how to style statement items by observing Fran Fine’s style. I identified key items in her closet and made a whole series about “How to Dress Like Fran Fine”. While I was doing research, I came across Brenda Cooper’s book - The Silhouette Solution. Reading this book has reaffirmed a lot of my observations of Fran Fine’s style, and taught me even more!

If you don’t want to overspend on clothes and still feel like you have nothing to wear (like I did for so many years), or be overly distracted by the relentless trend cycle, then it makes sense to devise a system (vision), or follow one. I only started doing this myself recently. I started identifying the things that were important to me - investing in good quality basics and well constructed items, and learning more about fabrics. I’ve done a closet audit, and sold and donated a lot of the pieces that didn't fit me right or that I simply was not wearing. I realized that I had spent so much money on items that I didn’t wear. It made me feel like I needed a different approach to fashion. 

A fun Fashion Philosophy

What I love about The Nanny and designers like Franco Moschino is what they represent when it comes to fashion, that it should be fun, and you should wear what you like, regardless of the trends. I love to have fun with fashion. But without some sort of system, I feel like I just overspend and over-consume to try and fill a void. This is bad for my wallet and bad for the planet. Following a system when it comes to fashion can actually be fun. It makes it so that everyday when you get dressed, you are enjoying the process, and feeling good about it. For me this is a great feeling and very different to what I felt before. Before, my fashion rush came from buying things online. Online shopping would provide me with a hit of dopamine that would fade pretty quickly. Getting dressed was never fun because I couldn’t make heads or tails of my closet. 


I don't follow a strict system, but it is nice to have some sort of method to the madness. I like a lot of Brenda Cooper’s tips and have some of my own too, which I want to share because they might help you on your fashion journey. If you think following a system sounds boring, look at Fran Fine. She is a fabulous diva who always looks good, has fun with fashion, yet sticks to certain staple elements.

Tip #1 - Develop a Healthy Skepticism of Marketing and Trends

As I mentioned above, the trend cycle moves fast. It’s hard to keep up with, and easy to overspend. This is by design. Marketers want you to spend your money and make impulse purchases. It is important to be very discerning about marketing. Influencer marketing can be so sneaky and tempting. These influencers are constantly showing up on your feed selling you things that you don’t need. Most of them are selling you flashy trendy items for that quick impulse purchase, instead of the high quality wardrobe basics that will last you for a long time and prevent you from constantly needing to buy new things to feel something. A lot of influencers on Tik Tok are also telling you what is and isn’t trendy, and it is important to consume that content with many grains of salt. I do consume this content too. I used to internalize it a lot more than I do now. For example, one influencer said that only light wash jeans look good, and then I didn’t buy or wear any dark wash jeans for a while! I realized that this is just one person’s opinion and not fact. By developing my own style I can more easily discern an opinion or trend and not feel like I have to incorporate it into my style philosophy.

Another example is all of this talk on fashion Tik Tok about the “old money aesthetic”. Conveniently picking up momentum at around the same time as Chanel (an “old money” brand) raised their prices. This “it” aesthetic is very expensive and therefore unattainable to most. If you like any of the “it” aesthetics that have come and gone, that is great if its part of knowing what you genuinely like. I personally haven’t liked many of the recent ones. The “old money” look isn’t my thing, I like bold colors and patterns. Why would I follow a trend that is unaffordable, unattainable, and also not in line with what I like? If what you like isn’t trendy or in style at the moment, who cares? You gotta wear what makes you feel good.

Brenda Cooper puts it in a great way “The fashion industry programs us to think that if we wear the latest trends that we will automatically look fashionable and attractive, but that is not the case...Keeping up with the latest fashions is a no-win situation that can cause women to ride a roller coaster of insecurity when their bodies or clothing don’t align with the current moment. Today’s fast fashion is actually designed to make you feel out of fashion before you’ve had a chance to hang your new clothes in the closet!” She goes on to say that you can take back control of your emotions and closet without getting sucked into the never ending tornado of trends. As you become more discerning you will make better decisions about your clothing purchases and get to know your own style, instead of being influenced by what is fed to you by the fashion industry. 

Tip #2 - Do a closet audit

Sometimes we buy things just to feel something (I know I do). It is too easy to end up with a closet full of clothes that you don’t feel satisfied with. 

I am sure that you go through your closet ever so often and pull out things to give away. I encourage you to tackle a closet audit with a different mindset. It isn’t necessarily about getting rid of anything, initially, although that is a helpful step too because decluttering is important. But this is more of an observation exercise. Brenda Cooper advises you to take a radically honest look at at your wardrobe and identify the clothing items that fall into three categories: 

Camouflagers - clothes we use to hide our perceived imperfections

Trends - items the fashion industry has told us we should wear to be stylish

Approvals - clothes we wear to fit in or impress others

The point is to bring unconscious influences to your conscious awareness to better understand your relationship with clothes and fashion. 

When going through your closet and categorizing the different items, ask yourself: Do I love this? Do I feel confident when I wear it? Do I feel like myself when I wear it? Observe the thoughts and feelings that come up

Doing this type of exercise has helped me develop my personal fashion philosophy, and has helped me make better shopping decisions. For example, pulling out trendy fast fashion clothes that I never wore, or only wore once, that were cluttering up my wardrobe made me realize that I wasted a lot of money. I no longer shop at fast fashion brands like Zara, Aritzia, and H & M because those clothes did not make me feel good about myself. The cut and construction didn't make me feel elegant or sexy. They fit me weird and the low quality fabrics were uncomfortable. I would rather invest in pieces that make me feel good. These days places like Zara and Aritzia are actually pretty expensive considering the quality. You can spend a similar amount on second hand designer clothes on sites likes Poshmark or The RealReal. 

Tip #3 - Invest in the basics and build a solid closet foundation

This is something that I am still working on, as I do like flash and sparkle! But when I struggle to get dressed for day to day activities, I realize that I need to think more about the good quality basics that are easy to throw on, comfortable, and flattering. For example tailored black shorts, and a black miniskirt. I literally just bought these items and I can’t believe that I didn’t already own them. Overspending on impulse purchases took away money and attention from buying the pieces that tie a whole closet together.

I want to feel good no matter what activity I am doing and I want to feel good in my skin. This has been hard for me over the past year. I had a massive fibroid in my uterus, it was 11cm x 11 cm and made me look like I was 5 months pregnant. I knew something was off with my body, but it took months to finally figure out it was a fibroid. I felt uncomfortably bloated for months. I felt like I had to dress to hide my belly. My surgery was 3 months ago and I feel a lot better, but my midsection doesn’t feel back to normal. I still get bloated easily and I feel like my hormones are all over the place. Feeling comfortable has become a priority for me. I still want to look good though, and I don’t want to hide. Wanting to wear flattering clothes isn’t always about the male gaze. When I had a slimmer midsection I felt like I could throw on anything and look good and be comfortable. That isn’t the case for me right now, which makes getting dressed a little harder. Good basics are playing a bigger role for me now than they did before.

As Brenda says “Looking fabulous, feeling confident, and stepping into your best self has little to do with hiding perceived flaws, chasing trends, or seeking approval. It has everything to do with wearing attractive, comfortable, stylish clothes that flatter your body and your personality.” Her Silhouette System is great and focuses first on building the foundation of your wardrobe. If you want more details, I highly recommend reading her book. The gist of it in terms of the basics are four tops, four bottoms, and 8 shoes. These items are a synch to mix and match, and then add your own flare to with “personality” pieces, or what I like to call statement pieces. Watching The Nanny you can really see her system in action.

You don’t have to follow this system exactly to get some great insights and advice that you can incorporate into your own fashion philosophy. 

Tip #4 - Find Your Style ID

There is so much that goes into finding your own personal style. It’s about where you’re at in  your life, what your day to day looks like, what makes you feel good, what makes you feel powerful, and whatever else you have going on. It takes some self-discovery, which is a lifelong journey! But it is helpful to have some guidance when it comes to clothing purchases. My personal style is always changing and evolving based on where I’m at in my life. I usually like to make a statement with my fashion. Unless I am feeling insecure, then I want to hide. But overall, I like to be bold. 

Finding a fashion ID isn’t about labeling yourself as one thing and never changing. It’s not a rule book to follow, but some guidelines that can help you make better decisions. Typically you won’t just identify with one style ID, but even identifying with 2 or 3 gives you a little more direction. 

Brenda has a great little quiz in her book to find which of the great 8 style IDs you are. It is a good place to start if you have no idea how to define or verbalize your own style or what you like. I’m sure there are tons of other quizzes online too.

I feel like I identify the most with these 3 style IDs - The Bohemian, The Glamorista, and the Elegant Sophisticate

Tip #5 - Ask yourself a few questions before making a purchase

Basically you want to assess, before making a purchase, if the item fits with your vibe (style ID) and if you will actually feel good in it and wear it. You want to make sure that you are buying it for the right reasons and not because it’s a flashy trend being sold to you. There is nothing wrong with pulling inspiration from influencers, and all over the place really, we just want to be more conscious about our shopping choices and spending habits! A fabulous diva is financially responsible too! 

Something that works for me and slows me down when making purchases is to ask myself a few questions before I buy something:

  • Do I already own something similar? If so, does it need to be replaced with something that is better quality, that will fit better and last longer?

  • What is the fabric content of this item? Will it last, or fall apart after a few washes? 

  • Can I find this item second hand? 

  • Can I create at least 3 outfits with this piece with items that I already own? 

  • Does the color(s) of this item fit with the color scheme of my closet? 

  • Is this an impulse purchase, or something I have been eyeing or thinking about for a while? 


What has also helped me is having a wish list of items that I want and giving myself a “cooling off” period. This prevents me from making impulse purchases. Basically I keep a running list of things that I want, for example a color blocked Moschino Jacket, a wool turtleneck, silk shorts, etc. When I see something I want, I refer to my list. If it isn’t on my list I add it, and give myself at least a week before purchasing it. If it is on my list, then I still give myself a few days to mull it over before pulling the trigger. I used to have a big problem with impulse shopping so this helps me a lot.

Take Baby Steps

Creating your own fashion philosophy is about the journey more than the final destination. A lot of it is removing distractions - cluttered closets, the fast paced trend cycle, marketing, influencers, impulse purchases - and getting in touch with yourself.

As Brenda Cooper says “Feeling confident and empowered by your wardrobe is about balancing the proportions and geometry of your body, not about wearing the latest trends”. 

I am still on this journey myself, and I found Brenda’s book to be very helpful. I love the work she did she did on The Nanny, and she won an Emmy for it too! Hopefully her tips and mine can help you on your fashion journey too.

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How to Dress Like Fran Fine Part 2