Finding Your Personal Style and Why It Will Free You From Worrying About Seasonal Trends and Others’ Opinion about What You Wear
Wednesday August 3, 2022

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Hats have for as long as I can remember captured my affection and interest. Perhaps it began with Mayim Bialik’s Blossom, a sitcom in the 90s. Yep, I then was inspired to find and eventually did welcome home a similar floppy hat with a large faux blossom on the front. However, I don’t remember ever have the courage to wear it out in public, but I oh, so, wanted to. 🙂

Fast forward into my late twenties, and I garnered up the courage to finally wear hats in public; this time structured wool newsboy caps, and while few, if any, other women were wearing hats, I kept donning them from time to time. Moving ahead into my thirties, and I forgot about my love for hats, as my head typically didn’t fit the average styles for women and my budget didn’t allow for custom hats as I didn’t know where exactly to shop, so it wasn’t until my trip to Provence that I purchased a sun hat, which was a necessity, and gradually found myself being reminded of my love for hats, if only I could find brands that enabled me to wear a hat without getting a headache (i.e., larger sizes, I wear a 59 cm).

Unconsciously, my return to wearing hats more frequently both in public and out in my garden, paralleled with my gradual courage to live the life I had always dreamed of, that didn’t make sense to most, but, as I share in detail in my new book The Road to Le Papillon, had been a yearning from decades.

Fast forward to today, 2022. There is rarely a day during the warmer months that you won’t see me in a large-brimmed straw garden hat when I am pottering about in the dirt amongst my plants, and just recently, I finally found a Panama hat that fits my head comfortable and is a style and color I love (seen in the pic above), so I have been wearing that when I head to the market or even to do errands as my primary accessory that serves a dual function of necessity and style.

All of this is to say, when I became clear about who I was dressing for (to feel my best self and not to impress others or wear a trend) and understood myself (in this case my head size as well as what made me feel good), I also gained the confidence and assurance from myself to wear without seeking approval what I loved wearing. The gazes or long stares, if they happened, while I may notice them, don’t pass my thoughts, whereas before I would conscientious and unconsciously quail a bit, not fully being myself in whatever situation it may be.

And yet, here is another truth I realized upon reflection, when it came to my teaching uniform, I felt hands-down confident, and owned it and enjoyed what I wore. I wouldn’t think about the outfit I had chosen once it was selected and confirmed in the mirror before heading to work because I loved it for my reasons, not the school’s or the people around me. However, in my personal life, this confidence took longer to find, and for all the reasons I write about in my new book, I now know why. But no longer.

“Consciously or subconsciously, there’s a disconnect when women are not dressing for—and by for I mean really for—themselves, like cheerleaders, all rah rah. Joy is just harder to attain.” —Stacy London, stylist and author of The Truth About Style

Perhaps you too knew your personal style in a particular or previous chapter in your life, but for some reason, you can’t put your finger on why what you wear now doesn’t fit you as well as you know clothes, if you loved them, would. Perhaps it has to do less with the clothes and more with where you find yourself in your life. Are you wrestling with finding true contentment? Are you debating about the path you currently find yourself? Do you feel confined in your current roles or responsibilities and expectations? Is there something else you long to express or now have the courage to share, thus embracing your full and true self with the world?

“Style teaches me over and over how to live in my skin. It helps me find courage and confidence and control when I feel I have none . . . I love the world of style n ow because I understand its transformative power.” —Stacy London

Whether we are dressing for others or dressing for a past version of ourselves or as the person other people perceive us to be but we know we are not, if we are not being true to ourselves, we have not found our personal style. When we have the courage to honor our true selves, the door to discovering our personal style opens, and while it will take time to edit and shop for our capsule wardrobe that aligns with our newly embraced personal style, we now have the key to the door and can be confident with the purchase of each piece because we know what makes us feel good, confident and grounded.

“Understanding yourself, developing your image, and updating your style takes the sting out of anyone else’s judgment and puts you in the driver’s seat.”

Today I would like to share with you ideas to consider once you have discovered your true self and have vowed to honor it, embrace it and revel in what you are fully acknowledging. On the topic of finding yourself, or returning to your true self, I recommend reading/listening to this episode/post and/or reading my The Road to Le Papillon: Daily Meditations on True Contentment.

But first, I want to begin with what I find to be reassuring when it comes to trends and personal style. As shared in this FT Weekend podcast episode, trends are becoming less relevant in today’s fashion culture and as shared by Lauren Indvik, The Financial Times fashion editor, “We’re now in this post-trend era where it’s a bit uninteresting to dress in what’s new or what designers or magazines or stylists or celebrities are telling you to wear. And it’s all about individual expression.”

With that said, I would argue, individual expression through sartorial choices has for decades been part of generations; however, the access to inspiring others to do the same is more prevalent and readily available to the masses due to social media. So does that mean that ‘individual expression’ is actually the new trend?

The truth remains that we must still have the courage to hold fast to the most genuine expression of our true selves, and only you will know what that is. Indvik defines our individual personal style as well as points out a style truth to ponder “what you wear to feel like the most exact version of yourself. And that’s really challenging too, actually, because you, who you are and how you think about yourself — that’s always evolving”.

As we understand ourselves, we then open up the door to find our personal style, and that has the potential to be a very enjoyable journey. Let’s take a look at a list of ideas to consider when embracing what is most genuinely you and supports how you live and enjoy engaging with the world.


1.Enjoy observing trends, but no longer feel pressured to purchase them

Fashion is an industry. Industries are meant to make money. Fashion makes money by churning out trends that we scramble to keep up with . . . The fashion industry keeps us on a roller coaster of expectation and disappointment. It’s built on, and thrives on, our collective insecurity.” -Stacy London

When we understand the purpose of the fashion industry, we can be more objective and less emotionally shamed into buying the latest season’s trend. No doubt, there will be certain trends that work with your personal style that you love and want to welcome into your capsule wardrobe, but the key is to first know your personal style and understand how the new piece will complement what you already have and why it works for you.

2. Make a list of what you feel most confident wearing . …

. . . Regardless of price, because at this moment you are not going shopping, you are just fine-tuning what you will keep your eyes peeled for when options cross your path, make a list of brands, specific items, styles, hem-length, waist-height, etc. that make you feel your most confident when you wear them. Whether it is because of what aspect of your body it highlights, the feel of a particular fabric on your skin, etc., what makes you feel both beautiful and confident?

On my own list, there are a handful of designers who while I don’t own any pieces as of yet from their collections, know that when I do find a piece I can afford and am confident the style works for my life, I will purchase it, and I will be confident knowing the piece will be with me and worn for many years to come.

3. Visit the designer shops or brands and try on what you think you love regardless of the price

Why? Because what you are trying to do is your homework on sizes, fabric and fit. Once you know which size for a pair of jeans from a favorite designer fits you best, you can then, heed point #4 below. . . .

4. Shop on The Real Real or other high-end or designer consignment shops

Once you know exactly what investment items you are looking for and in what size to fit you best, take some time to peruse on consignment shops. The Real Real is one of my favorite and trusted go-tos. I have found bags as well as clothing items that are high quality and available at a far lower price than what I would have had to pay for if purchasing it brand new. Also, it’s sustainable fashion.

5. Shop year-round, but not with a laser-focus

What I mean is, when we force ourselves to find a particular ‘something’, this is often when shopping becomes a chore. However, once we have an idea of what we are shopping for, we know that there isn’t a time-limit to when we must find it. Why? Because once we know what complements our true selves and the life we love living, the item will always be in style for us (until we evolve again). In other words, you will find yourself gravitating to certain shops, designers, brands, etc. Let yourself do this. You may not be able to buy what you find, but you can bookmark it and watch and see if it goes on sale or save until the price is within your budget. At least you have found what you love and know where to find it when you are able to purchase it, rather than the other way around, not able to find what you know you need.

6. Keep a list of what you love and would like to welcome into your capsule wardrobe

This item goes along with #5 because once you know what you love and what works well for your life, having a list with you (save it in the ‘Notes’ app, or on a page handwritten in your planner, somewhere that is with you when you potentially will be shopping or be around quality clothing) will ground you in certainty that what you have found either is or is not something that aligns with your personal style. Why is this confirmation important? Because of #7 just below . . .

7. Don’t be afraid to invest in items

Because you are no longer at the mercy of seasonal trends, when you purchase an investment item, you will be able, and want, to wear it for many seasons to come. Indvik advises “buying a very few high-quality pieces that you need and that you can also imagine yourself wearing 10 years from now. In the industry, we call these investment pieces and there are things that you’re gonna wanna wear all of the time and are gonna make everything else that you own look good”.

An example of such a piece would be a Burberry trench – whether you buy it brand new or consignment, or a pair of Roger Vivier flats – even if you wear the soles out, you can have them resoled, and the high quality shoe itself continues to look great because it was well made.

Even if you only allot yourself to purchasing one to three items each season as the fall or spring roll around, if they are investment pieces, you will purchase them confidently knowing your money will be creating outfits for you to wear for many seasons to come.

When you think of your money as something, that it rightfully is, hours of work, you don’t want to spend your hard-earned money on an item that won’t last but a few wears or a single season. Let your money be exchanged for something that will last.

8. Ask yourself, ‘What could I not leave the house wearing?’

On the flip-side of figuring out what you love, ask yourself, what could you not wear because it would not make you feel comfortable? This will help you narrow down what you do feel comfortable in, and then give yourself time to explore the ‘why’ of your answer.

9. Do not hesitate to wear the same thing multiple times a week

You don’t have to wear the same outfit (but you absolutely can), but what you should do, if you know your personal style and have a uniform for work or working out or errands or going about your everyday, you should be wearing pieces or the entire ensemble a couple times each week. It’s what you feel comfortable in and if the items are high quality, they can withstand being worn more often.

10. Buy colors that complement each other – make your wardrobe versatile

I have shared this idea for what we pack when we travel, but I think it is just as valid for our everyday wardrobe as well. Not only does it simplify, but it enables many options of mixing and matching what you have in your closet, because if the items are high-quality, you will be able to mix a blouse purchased in 2015 with a new pair of pants you purchased this past spring if the colors and textures complement each other.

11. Invest in accessories

Indvik’s advice to anyone who has a limited budget is to invest in accessories such as shoes, outerwear, handbags, anything that will elevate mid-price or mid-quality pieces – a pair of jeans and a t-shirt for example. Why? First, these accessories will last a very long-time if they are well-made, and second, they ‘ice the cake’ so to speak. They assuage doubt to the on-looker’s eye that the outfit isn’t intentional or elevated. When you have a designer trench, you can wear sneakers and a hoodie underneath. There’s no doubt that you know how to both look nice, yet be comfortable as the situation requires. And most importantly, accessories go with so many of your outfits, rather than just one or two.

12. Pay attention to the quality, always quality over quantity

While yes, trusted luxury brands dependably make quality items available, not all of their pieces are worth spending the extra money. Meaning, what does the brand do well? Focus on those items from that brand, and then search for other brands for the other pieces that make the other items well. Look at the quality of the fabric, the craftsmanship, certain brands do different things better than others, so don’t feel you are married to one particular brand to purchase all of your clothing, handbags, etc..

And the other reason to always choose quality over quantity when it comes to your personal style, you want it to last and look its best for a long period of time. Why? Your personal style, once you have solidified what it is, is not going to change for a very long time, no matter what the trends are, so make sure the items you invest in will go the distance.

Also, Indvik reminds, remember what you are paying for when you purchase an item – who made it, what are the labor practices in that company, how much are the workers being paid? If you are paying pennies for something, keep in mind, someone had to make it, and if the company cuts cost, they are likely reducing the quality and potentially not paying their workers well. Part of paying for an investment item is ensuring quality in the work practices as well.

Why should I concern myself with creating my personal style?

“Style isn’t something stagnant. Like us, it’s always in flux. It’s a valuable exercise to reassess your style, to see if it reflects where you are in your life and not some old notion of who you were . . . it’s never about the clothes—it’s about what they can do.” —Stacy London

Now you may still not be convinced that tending to and investing in our personal style is worth our time and exchanging our hard-earned money, but as Stacy London shares above, what we choose to wear has power, and since we have to wear clothes to go about our lives as we engage with the world, why not let the clothes underscore the truth of who we are, but in a supportive role.

“By changing your style, you’re forced to change the way you perceive yourself. And if you can see yourself differently, you can start to feel differently.” —Stacy London

Once you feel the internal boost of confidence wearing the right outfit can give you because you know you are wearing it because you love it and seek no one else’s approval, there is a loss of insecurity which lifts a burden that you may not have known you were carrying. When that burden is lifted, much like a bad head cold finally clearing up, you are freed to engage fully because what is really happening is that you are aligning your deep core of clarity about who you are with the person you present to the world.

“At any moment you can evolve to integrate who you are with where you are right now, instead of fighting it and holding on to outdated beliefs about yourself.” —Stacy London

And not only will people begin to understand who the real ‘you’ is, you will begin to strengthen an inner confidence and self-knowing that enables you to feel secure with uncertainty and the unknown that we have and will always dance with in our lives, and when we can become comfortable with not knowing, we are set free to live fully in the present moment, and that is the magic of living well.

“If you change what you see, you begin to perceive yourself differently.” —Stacy London


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11 thoughts on “Finding Your Personal Style and Why It Will Free You From Worrying About Seasonal Trends and Others’ Opinion about What You Wear

  1. I love this post! I will definitely ponder the great deeper aspects of personal style but what caught my attention is the discussion on hats. I love hats and have several types. Boldly wearing them wasn’t my issue…but getting too warm and sweating (to be indelicate) was. I adore huge sunhats, but me and my hair were always a mess after. I’ve had to take my boldness further and now sport a white lace parasol (from Victorian Trading Company, so cute!!) when I do find myself out in the sun for a period of time. I am so fair skinned so this isn’t often but I, as Shannon mentioned, am able to dismiss any strange looks I get. In fact, I most often feel somewhat admired (or, rather, my parasol) and hope I’ve inspired some to “do” sun in their own unique way. Style is so fun and there is so much to choose from, we just have to listen to what truly draws us and go with it!

    1. Melissa,

      Thank you for sharing how you embrace and express your true self through your personal style. I have no doubt you are indeed admired because you are exuding a confidence that is appreciated and they see your calm which would be wonderful calming energy to be around. Thank you for sharing your experience and your encouragement to others. I appreciated your comment and enjoyed reading it. 🙂

  2. Oh my goodness, so much yes! I have spent a lot of time working on my personal style this year, and it feels incredible. I’m on vacation currently, and I love everything in my suitcase for the first time! Even at home I’m excited to put myself together for the day because I feel great. Bravo, again, Shannon!

    1. Marina,

      So happy to hear! What a wonderful, calming feeling to know you know yourself well and feel comfortable in what you have chosen to wear because it truly reflects who you are without apology or hesitancy. Continue to enjoy your vacation in Italy! It sounds like an amazing destination your visit with family and the village. Ciao!

  3. Not so long ago, a family member felt quite comfortable (as the elderly often do, sans filter) that my “style” was quite boring. Her festooned hat, statement necklace, earrings, brooch, and rings were the epitome of style to her, and perhaps her generation. In many ways, classical style with a set or two of pearls is rather boring but I learned my comfort zone years ago. I do have some investment pieces, some at least a decade in age. They still work. I admit to a bit of a shoe and bag problem, but delight in knowing that I don’t have to think about what to wear in public. At home, I am more casual with some items that probably should go to the great disposal bin in the sky, but I see a few more weeks in their life, particularly when gardening or painting, dirty chores. But mostly I try to be “ready-to-go” every day, so once I am dressed, I am done. The evolution of personal style is an important component of knowing oneself. There is an honesty in that, a centering of the soul that drives one to enjoy life and embrace change that helps us grow. We are often challenged by family and friends, or even strangers who question our style choices and our personal direction in life. Being comfortable in our own skin is one of the greatest, and most hard-earned gifts, we can give ourselves! I have a few hats, I have popped them on now and then, but my head is just all wrong for hats, except in winter when I pop on one of my knitted caps to keep from freezing!

  4. Lucy, loved your statement “Being comfortable in our own skin is one of the greatest, and most hard-earned gifts, we can give ourselves!” Thanks for that!

  5. I really enjoyed this post. I have been, and still am, honing my personal style. I notice more lately what I feel my absolute best and most well out together in. That’s not to say I still don’t make the odd rash purchase that I later question. I love the idea of listing items, brands etc that I feel best in for reference.
    Thanks Shannon,

    1. Hi Sarah,

      I am also honing my personal style. I am very slowly building my capsule wardrobe and finally invested in a Ralph Lauren trench coat. It had been on my list for quite some time and when one was included in the recent Nordstrom anniversary sale I quickly added to cart. I am slowly adding natural, luxury fabrics like silk, cashmere, and linen piece to my wardrobe and feel most comfortable in those.

      Thank you for sharing!

  6. I, too, have a larger-than-average head and have struggled for years to find an attractive sun hat to fit my noggin and my style. I found an item earlier this summer at Talbots and have been pleased with it: a visor that looks like a classic boater and is adjustable.

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