Why Your Wardrobe Doesn’t Feel Like You—And What to Do About It

If you’ve ever stood in front of a wardrobe full of clothes thinking,

“Why don’t I have anything to wear?”

—you’re not alone.

Recently, a reader emailed me and said “I’d love some help with getting my wardrobe more organized and stop buying clothes that don’t suit me. I tend to admire certain styles on others, but they don’t feel like me. What’s the solution?”

This question gets to the heart of a silent struggle many women over 40 experience: the disconnect between what we think we should wear and what actually feels aligned with who we are.

Let’s unpack this—practically, psychologically, and personally.

Step One: Clear the Clutter, Kindly

Before you can find your style, you need to see what you’re working with. That means doing a full wardrobe audit—not just a tidy-up. Try everything on. Ask:

Does this fit me now—not five years ago?
Can it be altered, or is it time to let it go?
Do I feel good in this—or just guilty for buying it?

Let go of clothes that don’t serve who you are today. Holding on “just in case” creates decision fatigue and keeps you stuck in the past.

Step Two: Ask Not “Does This Look Good?” But “Does This Feel Like Me?”

Here’s the truth: just because something looks amazing on someone else doesn’t mean it will feel right on you. Style isn’t copy-paste—it’s a form of self-expression rooted in your personality.

That’s why the most important filter when shopping (or decluttering) is not “Is this trendy?” or even “Is this flattering?” but:

“Does this feel like the best version of me?”

Admiring someone’s style doesn’t mean you should emulate it. Often, what you’re really drawn to is the confidence they radiate from wearing clothes that express their essence—not yours.

Step Three: Decode Your Style DNA

The missing link for many women isn’t taste—it’s translation. You know what you like. But how do you translate that into what actually works for you?

A great exercise:
Look at three outfits you love wearing and three you never reach for. Compare them.

Is it the colour, the shape, the fabric, or the mood that makes the difference?
Do your favourites feel relaxed or refined? Bold or soft? Sculpted or fluid?

This isn’t just “spot the difference”—it’s discovering the patterns in what feels authentic.

And yes, it often comes down to more than just fit or trend. It comes down to personality.

Why Personality is the Foundation of Personal Style

Your wardrobe should feel like a reflection of who you are, not who you used to be, or who society says you should be.

This is one reason I created the 7 Steps to Style program. It’s not about telling you what to wear—it’s about giving you a system to understand what feels right for you. When you know your unique combination of:

Colouring
Body shape
Personality style
Values
Lifestyle

…you gain the clarity and confidence to walk into any store and instantly know,
“That’s me—and that’s not.”

You’ve Changed. Your Style Should Too.

If something worked for you 10 years ago but feels “off” now, that’s not a failure—it’s evolution. Midlife is a powerful time to reclaim your style with fresh eyes and a deeper sense of self.

You don’t need a bigger wardrobe. You need a more aligned one.

Let go of the idea that there’s a “must-have” list for everyone. There isn’t. There’s only what’s right for you.

And when your wardrobe starts to reflect that truth, getting dressed becomes effortless, affirming—and yes, even joyful.