At 50, I have a fully functional and fab-for-me wardrobe that is a good reflection of my sartorial preferences, beliefs, values and personality. I’m happier with my style than ever, and it’s a great feeling. But it wasn’t always that way. Over the years, I’ve made plenty of style mistakes, wasted money, and learned the hard way. It seems that whenever I stray too far away from what is a natural and authentic match with who I am, it bites me in the bottom. But I don’t regret trying and failing with different looks and items over the years, because sometimes you only know what’s right when you try something that’s wrong. The confirmation — which only comes later — is validating and satisfying.

As I think back to my style mistakes, I shake my head and laugh. Finding an authentic personal style is a journey, and quite the test of our patience. At worst the mistakes were a waste of time and money, and at best I learned from them. I’m sure there were more of them, but these are the style mistakes that spring to mind.

1. Boho from Head to Toe

When I went to varsity in the late ‘80s at the University of Cape Town to study psychology, there were two style tribes in the faculty of Social Sciences and Humanities. Dressy, polished and branded Preppy with lots of glitz, and ultra casual earthy Bohemian Hippy with zero glitz. The two tribes could not have looked more different. I fell into the Preppy tribe because it was colourful, dressy, crisp and polished. Yet there were aspects of the boho style that appealed to me, especially in a hot African Summer. So I began adding those types of flowing and breezy pants, tops and dresses in earthy boho patterns and ditsy florals to my style, along with beaded necklaces and brown leather shoes. Well. It wasn’t me, although I was very cool and comfortable in the heat.

Later, my wiser self realized that the right flowing boho blouse or dress makes me happy because it’s pretty, elegant and romantic. But it needs to be in a sour bright, white, or my shade of blue, and styled in a crisp way with white footwear and my pearls. Boho-Lite is the way to go.

2. Oversized Instead of Fluid

Back in the ‘80s, I loved to wear oversized tops with gigantic shoulder pads and waist and hip-cinching belts. The broad shoulder line of the shoulder pads and the belt cinching created ample structure back then, as did the skinny jeans. Over the years, I’ve tried lots of oversized shirts, blouses and pullovers, hoping to rekindle my ‘80s fashion love, but without the shoulder pads and waist cinching this time round. I feel sloppy and unkempt in today’s oversized silhouettes. My narrow shoulders prevent an oversized top from staying put, and my small frame is lost underneath. Semi-tucking and sleeve scrunching does not help. No more.

Later I learned that fluid fits suit me down to the ground. They are roomier than tailored fits, but not as roomy as oversized fits. As long as the neckline is high, fluid tops stay put. They tuck and semi-tuck well, and I especially love them with a welt at the hem. I can also wear an oversized and architectural cotton shirt or shirtdress when there is ample structure in the neckline and sleeves.

2. Too Much Black

I went through a phase in 1994 and 1995 where I wore a LOT of black, and black from head to toe almost every day. I was a retail buyer at the time, and the rag trade wore lots of dressy black because it was the trendy thing to do. As an impressionable 25 year old, I thought I’d look more grown-up and that people would take me more seriously if I wore a lot of black. I’d also fit in with my peers.

My candid Mother was quick to tell me how all the black didn’t look or suit me at all. I was the gal who wore white and bright colours, and should stick to that. Of course, I ignored my Mum and continued with the all-black look because I thought I knew best. It never felt right, but I hoped those feelings would pass.

Of course, Mum was right. I missed the white and the colours. So I added back in shades of white to wear with the black, which felt better right away. I also liked to wear blue with black and white, so I added that too. Now I’m at the point where I don’t wear solid black at all. Dark blue is my black, and it’s staying that way.

3. Uncomfortable Trendy Shoes

For decades I wasted money wearing super cute trendy shoes that killed my feet. Platforms and flatforms that didn’t flex when I walked. Strappy sandals that dug into my skin. High heels that gave me foot cramp. Lug soles that were too heavy. It’s embarrassing how many times I bought shoes that were too wide for my low-volume feet, too short for my long toes, and hard as nails, hoping they would soften. Hobbling along at the end of the day was not unusual. Denying my practical side was unnatural.

Thankfully, I realized that I don’t need to wear uncomfortable trendy shoes to look fab. Slowly, but surely, I learned which shoe styles work best for my feet and walking lifestyle. These days I don’t compromise at all. I am set in my ways wearing modern classic and very comfortable footwear. That’s that.

4. Overly Casual

I like to wear dressy clothes because it makes me feel fabulous and pulled together. I like glitz, luxe fabrics, tailoring, white wardrobe items, polish, and lots of refinement. Every time I bought a (non-loungewear) clothing item that was very casual, it was seldom worn. When I did wear the item out of guilt for spending the money, it never felt right, even when I tried to dress it up.

I’ve learned to ask Greg what he thinks of the very casual clothes that occasionally follow me home because I’m attracted to them in some way. He asks me, “Is that loungewear?” When I say no, I know I’m about to make a style mistake again.

5. Strict Instead of Playfully Pretty

About eight years ago, I went through a style phase that incorporated a more androgynous, hard-edged, and stricter vibe. More neutrals, more minimal, fewer bright colours, fewer romantic and flouncy design details, and far less soft all round. I can’t tell you why I evolved my style this way, but it felt quite good at the time. So much so that I almost didn’t list this as a style mistake. It was like a phase I needed to get out of my system. I even left off my pearls, which greatly shocked my clients and some forum members. I got the phase out of my system and learned invaluable lessons along the way.

Now that I’m back to sporting a softer, brighter, more maximal and playfully pretty style, it’s like coming back to a very familiar place. Adventures are fun and exhilarating, but the comfort and the safety of home is hard to beat.

If you feel like it, share some of your own style mistakes in the comments section, and explain how you came back home.