What Not To Wear In Midlife

“Can we still wear big prints like this?” asked my friend as she showed me a picture of a jumpsuit with large floral prints. The print wasn’t the problem. It was the silhouette. But it also got me thinking about this idea of what we can’t wear. Whether it’s because we’re too old, too big, or just too something…women believe that certain items are off limits.

So I decided to break it down in this post. 

Here’s 3 Things Women Should Never Wear

Outdated Clothes

Women should never wear outdated clothes. When I say outdated clothes, I’m not referring to what the fashion industry says is “out”. My definition of outdated is about YOU. I’m more interested in how you feel in your clothes. When you put something on — like a pair of jeans from 5 years ago—I want to know how you feel. 

Physical fit is important. You must be able to zip them up and move around. But do they still fit your style? Do these jeans from 5 years ago look like YOU today? Or are they more like you from 5 years ago?

Your clothes have an expiration date. As your life shifts and changes, you evolve. Your clothes must support you. Similar to how an actor’s costume must support the role she’s playing on stage. Your clothes must support your current roles in life. What were your roles 5 years ago? Specifically, what role were you playing when you bought those jeans? Was it your “mom of young kids role”? If yes, and that’s not your role anymore…it’s time to get some new jeans that support you as mom with older kids now. Or whatever current roles you assume. Because when we wear clothes from a previous role, it feels off. It’s outdated. (Go here to read how to reinvent your style if you’re feeling outdated.)

Energy Draining Colors 

I know many women who are obsessed with knowing “Their” colors. And I get it! Understanding which colors bring out your natural coloring in true harmony is a great tool to have in your back pocket when getting dressed. It helps you look more vibrant and alive. Just as wearing the colors that work against your natural coloring will drain your energy. It can make you look sick.


In my styling work, I’ve found that most women over 40 have an idea of what colors suit them. They’ve been getting dressed for so many years, they naturally gravitate towards their palette. Wear those colors that you know highlight your skin, hair and eyes!

But there’s another factor to consider when choosing color: how each one makes you feel. Some colors can energize you, while others might bring you down.


When I wear bright orange or red, I feel in my power. I also always get compliments. On the flip side, once when I was doing a client’s color palette I saw brown was in her wheel. When I presented this to her she said “brown makes me feel like poo!” My immediate reaction —don’t wear brown! So even if a color is in YOUR palette, it must energize you. Don’t wear colors that make you feel like poo. 

Someone Else’s Head To Toe Look

In a mom’s Facebook group, a woman posted about feeling frustrated because her body changed and she didn’t know how to dress for her new job. The comments were filled with Instagram links to influencers, with notes like, “She has a similar body to mine, so I buy what she recommends.“

UGH! This is why everyone is dressing the same — it’s algorithm driven!

I understand where this woman is coming from. Her body changed, she has a new role at work—everything is different now, and her old clothes don’t work. She’s in her reinvention era.

Sure, she could buy a bunch of stuff recommended by influencers. Some of it might even work. But this only skims the surface of her fashion dilemma. 

The real issue is that she doesn’t know what her style is anymore. (Or maybe she never did!) And wearing someone else’s look will only make it harder for her to find her own (along with perpetuating the cycle of buying more clothes she’ll never wear.)

What Not To Wear

If you catch yourself stressing about what not to wear, pause and ask why. Is it because you’re worried about what people might say? Or because you want to feel and look your best?

If it’s about other people, know this: you’ll never win everyone over, and you’ll waste a lot of energy trying. If it’s about you, then the key is confidence, and that comes from making choices you feel good about.

The way you build that confidence is simple: wear things, test things, get it wrong sometimes. Those “misses” matter because they teach you what doesn’t work, and that sharpens your eye for what does. Over time, you start to build trust, and that trust is what makes getting dressed feel easier and a whole lot more satisfying.

Click here to read Why We’re So Self Conscious (And What To Do About It)