You would think that by age seventy-six, I would have nailed my personal fashion style. Alas, I am still a work in progress, but who is ever fully confident in everything they wear all the time? Even Angelina Jolie found herself struggling to define her personal style when she recently launched her own clothing line. We always think we would look better if we just had those cute python boots or that gorgeous red coat. It seems we’re always on the cusp. Then, we take a look in our closet, wish we could throw everything in the trash heap and start over—if only we had the money.

This dilemma hit home when I read a recent column in the Toronto Star by McKenna Hart (Purging my closet and filling it with colour completely changed my life). She’s only twenty-four but wardrobe insecurity issues span all generations. Hart felt her clothes did not accurately reflect her authentic self so she put her entire wardrobe in storage and wore nothing but black for six months to clear her head.

At the end of six months, Hart was sick of wearing black and started her new clothing journey by purchasing only items she absolutely loved, items that reflected her true personality. Hart had the benefit of sterling advice from her therapist; “Start with what you like”. Sounds simple but we’re so susceptible to being influenced by fashion magazines, our contemporaries, and the media that it’s often difficult to parse what it is we genuinely love. Fashion magazines in recent years have done an abysmal job of showcasing what real women want to wear and have become totally irrelevant.

My personal shopping mantra has always been, if in doubt, don’t buy it. The inherent risk here is that sometimes when we go back to get something we loved but weren’t sure of, it is no longer available. I still feel the pain when I think about that white, loose-knit cotton sweater I passed over about a month ago. When I went back to the store to get it, they were sold out. If that wasn’t disappointing enough, the sales girl was wearing the very sweater I could no longer get.

Wants and needs are very different

In my own fashion journey, I have often been guided by advice to purchase classic basics: good black pants, a serviceable and practical winter coat, and tops that work with multiple outfits. That formula can result in a boring wardrobe and I do not like boring clothes. Even after decades of experimenting, I’m finding it difficult to answer the call of my heart, not my head.

A couple of years ago I discovered a little independent shop that carries artsy clothing lines that emphasize geometrical and drapey shapes rather than tailored, fitted cuts and I absolutely love their merchandise. They also have an assortment of colourful, funky jewelry to flatter and complement their looks. They do carry plenty of black items but their styles are cut on the bias or made with unusual textures and fabrics. The few prints they carry are daring and artistic. Personally, I always tire very quickly of any prints I buy so I avoid them. Jackie Kennedy never wore prints.

I find I now have better luck shopping in small, independent shops rather than the chains. I am also an Eileen Fisher fan, ignoring the criticism of her line as the last resort for women who have ‘given up’. Bull crap! Her fabrics are organic, top quality, and washable. Her clothes are timeless and last for years. EF is one of the few designers who recognize that baby-boomer women still love fashion. She designs for our real-life boomer bodies, not the teenage anorexic waifs most designers kow-tow to who share neither our taste in clothing nor our body shapes.

I am slowly easing into this new, less structured look. I never thought I would own a pair of baggy-legged, narrow-at-the-ankle dropped-crotch pants, but now I do. Those pants called for funky shoes so I got those too. I’m getting braver with colour and cut and I like how I feel when I wear something a bit different from what everyone else is wearing. It’s the right-brain creative side of me letting loose a bit, finally listening to my heart, not my head. I remind myself that I no longer have to dress for success in the corporate world. I’m retired and free to be me.

While I enjoy experimenting with another side of my personality, I have not totally forsaken good-quality classic pieces. I love my tailored black Spanx pants. They wear like iron and will probably last longer than I will. The same thing goes for good white shirts, preferably oversized and in a variety of cuts and shapes. I now pair them with statement artsy jewelry or a scarf. My motorcycle boots seem to work with everything, even my baggy dresses.

Closet purges are freeing

While it’s sometimes tempting to toss most of the items in my closet, I still hang on to a bit of the safe old Lynda armour. Mustn’t be too hasty. There are numerous websites, books, and blogs full of suggestions on how to purge our closets of items that no longer fit our bodies or lifestyles.

I am no expert but I have found some comfort in reselling my better-quality items on Poshmark. I’ve had more luck with Poshmark than using consignment stores but patience and willingness to take less than 25% of the retail value are essential for selling online. I’m also becoming more particular about which charities I donate clothing to and now try to avoid for-profit resale stores in favour of genuine charities.

I do like the suggestion of turning all your hangers 180 degrees. Each time you wear something, turn the hanger back the correct way, and after six months or a year, you get a clear picture of what you’re actually wearing and what should probably be discarded. It’s the old 80/20 rule: we wear 20% of our clothing choices 80% of the time. That’s a scary proposition but one that must be faced.

Fall is the time of year when as part of preparing for hibernation we are tempted to reach for everything black again. It goes hand-in-hand with craving carbs. In the past, I tended to default to clothing that was safe and boring when, in fact, I now really want to start over and push the boundaries, with colour, personality, and pizzazz. While I eschew trends, I am getting braver. Our personalities evolve, and so should our wardrobes. 

McKenna Hart sums it up perfectly at the end of her article as she describes starting on her own fashion journey: “Whether we realize it or not, everything we adorn our bodies with is an extension of ourselves. If you can let go of who you have been or who you think you should be, you never know who you might become.” I say, let’s do it! Are you in?