Some people figure out their fashion style early in life and then spend decades building on and improving that style. I am in awe when I see a young woman who already understands her personal style and goes into the world with confidence and flair.

I was not that woman. Style and I have a long and complicated history. I wish I could say that I have always been well-dressed with great hair, make-up and accessories. I aspire to be a woman who knows her style and is happy and comfortable with her choices. It is a work in progress.

More often than not, I have missed the mark. As I reinvent myself yet again in this stage of my life, I am not only older and wiser, but I think I have finally learned from the mistakes of my younger selves.

I think of my life and style in three stages. I had success and missteps in earlier stages that I can now bring to my current life makeover. Here are a few ways that my past mistakes helped me to get more from fashion after 50.

Young Professional Style

In the first stage, I was a young professional, just starting out in the work world. It is both easier and more difficult to get style right at this age. Physically your body is probably cooperative, things aren’t sagging and your joints work well. Your skin and hair glow. Your lips have natural color.

At this stage, you most closely resemble young fashion icons and models. You can experiment with a new trend and not look silly. You might not have much money to spend on clothing, but the stores that cater to juniors are often at the lower-priced end of the spectrum.

I think back both fondly and in horror of myself in this stage. I managed to put together a work wardrobe and quickly learned the value of basics that could be rearranged and accessorized to carry me through the week. I bought and loved staples such as black pants, a solid color jacket and simple shirts and sweaters. I learned that I could use some great earrings or a necklace to keep things interesting.

During this stage I also learned what didn’t work. I had a brief fling with prairie skirts, whose big ruffles and flounces did not suit me. I wore bright blue eyeshadow, which was not a good look either.

I often bought and wore ridiculous shoes. Remember those four-inch red heels that Olivia Newton John wore with the black leather outfit in the movie Grease? I had those shoes. I wore them to work. That memory is painful – not just for the discomfort of the shoes, but because I thought they were work appropriate. I also wore peep toe slingbacks in the snow. I was a slow learner when it came to shoes.

Family Fashion Basics

In the next stage of my life I was working long hours and raising my family. Time was at a premium and thinking about style barely made my radar. I needed work basics and discovered that quality trumped quantity. I bought classics that I could wear for years. Learning from my earlier shoe fails, I bought lower heeled pumps and wedges that were more comfortable. I also bought quality tote bags that were up to the task of carrying my planner, files and lunch.

My biggest mistake at this stage was that all my money and energy went into dressing for work. I had two types of clothing: jackets with dress pants and a shell, or old sweats that I wore to clean the bathroom. Informal occasions, such as a football game or dinner at a friend’s house caused fashion panic. I felt ridiculous wearing a suit, but I had little else to choose from. I was late for an event more than once because I literally stood in my closet trying to find something appropriate to wear.

When I look back now, I see that my wardrobe spoke to my priorities – I valued work more than leisure. It seems nonsensical that I didn’t just go and buy some nice, casual clothes. I didn’t learn the lesson that you need to have the clothes to support your lifestyle. A good pair of well-fitting jeans would have done miracles for my wardrobe. Another lesson learned.

Work from Home Lifestyle

Now, I am in yet another stage. I left corporate life and no longer need all those suits. I have started a business where I work from home. I have more balance in my life now and have more time for friends, family and recreation. I recognize and accept that my body is evolving. Along with these changes comes another style transformation.

This time, I think I might be getting it right. I want my style to be simpler and more basic. Instead of a short, professional cut, I let my hair grow longer and let my natural curls take over. I wear far less makeup and somehow manage to look younger. I want to be fashionable, but I refuse to be uncomfortable. I still love shoes, but I know there are stylish and comfortable options.

It has taken some trial and error and extra time in the dressing room to see what works well with my current body. I bought some comfortable, casual basics that I can wear every day. I add a jacket, scarf or necklace when I want a more special look. I struggled to find the right shoes in stores, but have found great options online. I still can’t wear ruffles and flounces, and I have no need for four-inch heels. I want to be stylish, but I don’t care about being trendy.

Finally, I have the right clothes for my lifestyle. It feels freeing, and I wonder what took me so long. I’m glad that I have been able to use the lessons from the past to lead me into the style I am creating today.

Have you always had a great sense of style? Or did you learn hard lessons about style and fashion along the way? How have you adapted and changed as you’ve moved through different stages of your life? I’d love to hear what is working for you in your life today. Please share your fashion journey in the comments.

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