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Quit Telling Us What to Wear!

By Susan Cox February 22, 2023 Beauty

There’s always a fine line between suggesting and telling. I have found this especially true when working with my clients.

My job is to teach you how to wear what you love, what fits, and what flatters, accentuate your shape and put it all together for your own personal style.

Sometimes changing the mindset needs some extra attention. In my years of styling Midlife women, I have seen it time and time again.

Why is this a thing?

Let me share why!

Let’s Take a Trip in the Waaaaay Back Machine!

Our first stop in the time machine journey is elementary (grammar) school circa mid to late 1960s. Girls were not allowed to wear pants of any type to school.

I vividly remember wearing essentially what was a jumpsuit without long pants. It was appropriate, and I loved it when my mother bought it at the Lemon Frog Shop at Sears! I couldn’t wait to wear it to school.

Until… lunch. It was then when the principal (a man) tapped me on my shoulder and said, “Susan, can you please come to my office.”


It was there that I learned girls were not allowed to wear pants, and I had to call my mother to bring me a change of clothes.

Ladies, this was traumatizing to me. And little did I know it was just the beginning of being told what I could not wear!

The Rules Continued

From the 6th grade to the working world, the rules of what was expected women to wear wore on (pardon this pun, I couldn’t resist).

When I entered the working world in the early 1980s, it was written in the HR policy, “Women were to wear skirts and or dresses. No pants of any type were allowed.”

Again, we were being told what we couldn’t wear.

And I will share that it was expensive to fill my closet full of ‘suits’ and dresses. Casual Corner was my go-to store during those times.

Then, single ladies became married ladies, and some went on to have families. Again, more labels and opportunities to be told what we couldn’t wear.

“You’re a mom; you can’t wear those jeans. You have to wear “Mom jeans.”

Then middle age entered, whether we were ready or not.

Another label, “Now that you’re over 50, you cannot wear that.” Perhaps it wasn’t as direct as other stages of our lives, but retailers made it quite clear what they thought of our clothing options for the midlife faction… pretty much zilch.

In fact, retailers really do not spend any of their marketing dollars reaching out to Baby Boomers, which is incredulous to me since we have the most spending power.

Our age does not dictate what we wear! Please read this again, lovelies!

Rules Are Meant to Be Broken

Whether you are a rule follower or not, I am here to tell you that you are free to wear what you want! But you probably already knew that, right?

When I work with my clients, we establish this from the beginning. What I do to make this a bit more simple and help them connect with their style is to have them address these two issues:

#1: What Makes You Happy

We gravitate to certain colors, textures, the way things are arranged and more. We want to pay close attention to this and identify why it matters. We are struck by how they make us feel. And there’s no reason that your clothes cannot reflect what lights you up!

Again, for decades, we’ve been told what we cannot wear, so sometimes our thinking is limited. When you surround yourself with what makes you feel good, things change.

Take a look at your surroundings; what colors are prevalent? What color combinations light you up? Are you attracted to specific textures? All of this matters.

I cannot tell you how many of my clients have connected with their true style by aligning it with their life experiences and what is important to them.

#2: Current Lifestyle

Are your clothes hanging in your closet right now? Do they support what you are doing right now in your life? If they aren’t, I encourage you to do a closet audit.

Then, I have my clients answer these questions to determine if the piece should stay as part of their wardrobe or perhaps be given to a charitable organization (where someone else can enjoy it as much as you did):

Have I Worn This in the Last Six Months?

Chances are if you haven’t, it may be time to take it out of your inventory. Many times, my clients who have had a life change such as retirement, still have their work clothes as part of their wardrobe. All those pieces are doing is taking up precious real estate. We should have what we love and what we wear in our closets.

Does It Fit?

Fit is so important when it comes to our clothes. If something that’s currently in your closet doesn’t fit can it be altered by a tailor? Or is it something that no longer serves you?

Do I Love This Piece?

How does this piece make you feel? Does it flatter your shape? Is the color right? We deserve to love our clothes, and I want you to take the time to really examine if what’s currently hanging in your closet makes you feel amazing every time you wear it – if it does, it stays!

Can the Piece Be Used to Create Three Outfits?

This is a game-changer, ladies. Our clothes should be able to ‘play nice’ together and work with what else is in our closets. When we don’t, we have ‘orphan pieces’, those tops or bottoms that really go with nothing. Again, pieces that are simply occupying space and not contributing to what we love.

You’re in the Driver’s Seat

As Glinda the Good Witch from The Wizard of Oz told Dorothy, “You had the power all along, my dear.” The same is true for your style!

What we wear is so much more than clothes. It’s how they make you feel, the power that you give them when you put them on! Age is simply an image, and I help beautiful women, just like you, to decide how you portray that image every single day!

Cheers to your style, lovelies!

Let’s Have a Conversation:

What is your experience with being told what you should or shouldn’t wear? At what time in your life did you feel the most restricted? Have you found your freedom of style?

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We must be the same age since I share the experiences you have. Dresses only to school though in the late 60’s we were allowed to wear pants on Friday (no jeans). Towards the end of the school year one year a teacher loaded up approximately 12 girls that the Principal determined were wearing dresses that were too short. They were taken home to change. My mom was freaking out because school was almost out for the summer and the dresses I owned I had nearly outgrown. This happened in my 3rd grade year..early 1960’s. Your journey in your working years were also what I experienced. Through all of these years I look back and remember the stress and unfairness all these rules were. I’m throwing off the assumptions of what a 65 year old woman “should” be wearing. I appreciate the tips you have shared! They are different than the same old gibberish thrown are way!


So glad you enjoyed the article, Laura!

Last edited 1 year ago by Susan
Jo Kennedy

I have pieces that I bought before I lost 20 pounds, many that were expensive. I am encouraged by your article, to donate clothes that I do not wear, no matter what they cost. Thank you!

Sandy Charbonneau

Your article stirred a lot of school clothing memories! Wow, you are right. I am heading to my closet now👌🏻

Sandy Charbonneau

PS. Anyone, please/This photo?? Where did it come from? How do I update it?


Great! Glad it inspired you, Sandy!

Jessica Simkulet

How well I remember my senior year in high school (1969), when girls were not allowed to wear pants/shorts. One Spring day, I decided to “test the system”: I wore a newly-purchased “skort” (shorts that converted to a skirt by applying buttoned flaps to the front and back….genius!). I began my school day with flaps ON, then removed them between classes. Of course, a teacher noticed and told me to go home and change (a 3-mile roundtrip walk!). I simply went to my locker where the flaps were stashed and buttoned them on. I saw the same teacher a few minutes later…..she was visibly surprised, but impressed! I worked my fashion magic a couple more times that day, which made a mundane school day a little more interesting!


I feel that I’ve been told what to wear my entire life. It’s humiliating at times. Now, I ignore any unsolicited guidance and wear what I like. Life is too short!

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The Author

Meet Susan Cox, Confidence Creator and Founder of Fiercely50ish where she helps Midlife women get visible with their style and shows them just how magnetic they are and let their confidence shine through by what they wear today and forever. Want to be comfy and stylish? Checkout her Athleisure Capsule.

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