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Why Your Quest to “Dress More Like A Woman” Should Be a Soul Check—Not Just a Shopping Trip

If you’ve found yourself slowly inching into the stage of life where running off of three hours of sleep is more of a liability than a flex, and shopping in the junior section gets you side-eyed from actual juniors who are probably wondering which niece you must be shopping for, then some variation of “I want to start dressing more like a (grown) woman” have likely run a few laps across your mind.

But let’s be real. Which woman are we talking about here?

When we say we want to “dress like a woman,” are we simply saying we don’t want to dress like a man or a little girl? Or are we picturing a specific kind of woman? One who is poised, polished and maybe a bit more… put together?

Are we referring to the soft-spoken, gentle woman who floats through life with pretty floral dresses and smells like peonies? Or maybe it’s the poised, “soft-life” girlie with the capsule wardrobe, Hermes sandals, and perfectly curated bracelet stack.

Which of these women will we cast as the official poster girl for what it means to dress feminine or “like a woman”?

The answer? Both. 

And quite honestly, neither.

Why? Because womanhood is not a monolith. 

When it comes to expressing womanhood, some women thrive best when they’re in their mother or wife element. Other women express it best through their creativity, leadership, business, or all the above. 

There’s truly no one way to be woman and likewise, there’s no one way to dress like one.

When done right, your style should be deeply personal and reflect you. The real you.

But that’s where things may get a little complicated. 

And exactly which “you” is doing the dressing?

See, sometimes, our closet is full of more than just cute clothes. Sometimes, it’s full of the traumas, insecurities, and pain we feel.

I’ll speak for myself: Growing up, I wasn’t exactly the prettiest girl in the school yard and guys weren’t really checking for me like that. But one thing that would always command the attention of my pubescent boy peers, though? My ripe and overgrown chest. 

It didn’t take long for me to figure out that if I wanted to be noticed and feel pretty and cool, I had to lead with the girls front and center. From low-cut v-necks to skin-tight tops, I made sure that my wardrobe left no room for doubt that I was worth a few playful teases in the hallways or, at  least to (please God) not be the last one picked for the softball team.

So yeah, for a while, it wasn’t me picking out my clothes. 

It was my insecurities and my need for acceptance, validation and attention.

Now let me ask you a question: Is the healed version of you getting dressed in the morning… or have you been letting the insecure or traumatized little girl still call the shots?

Maybe for you, this doesn’t manifest as you wearing skin-tight or revealing clothes like it did for me. Maybe you:

  • Dress super flashy, displaying opulence simply because you want to prove your worth.
  • Obsess about always looking perfect because you take comfort in hiding behind your clothes so people don’t see the real you.
  • Choose to wear baggy or oversized clothing because you feel self-conscious about your body or want to avoid attracting unwanted attention from men due to past traumatic experiences.
  • Wear basic clothes because you don’t want to be perceived.
  • Spend so much time following trends and trying to keep up with the Joneses just to feel belonging and worth.

It’s time to ask the “why’s” behind your outfit choices

A lot of these things aren’t innately bad. Flaunting your curves, choosing an opulent wardrobe, going oversized. The goal here isn’t to demonize any of those personal fashion choices. 

What matters, though, is truly the why behind it. 

If you’re choosing these ensembles because they truly resonate with you, your taste, your lifestyle, and your personality, that’s one thing. But, if you’re picking your outfits from a place of brokenness, that’s another.

It’s worth asking:

  • If you were healed and whole, would your current fashion choices change?
  • If your clothes weren’t trying to prove, protect, or hide something, what pieces would you part ways with? 
  • What would new pieces you embrace if you weren’t carrying shame or survival energy in your wardrobe? 

Maybe you would finally embrace wearing bright colors and bold prints because you’re free from the bondage of what others might think. Or, perhaps you would cover up a bit more, not out of fear or shame, but because you no longer needed external validation to confirm you’re beautiful. 

Who knows what new styles your soul renewal may unlock.

It’s not about looking feminine. It’s about being feminine.

Anyone can buy a few flowy dresses and kitten heels. That’s the easy part. The challenge is doing the work of healing so that you’re no longer letting the little girl call the shots on your wardrobe. Once you start healing and becoming whole, you’ll naturally start dressing like the woman you’ve been saying you want to dress like. Not because you’ve shopped all the pieces she wears, but because you’ve actually become her. 

See, your true feminine style won’t just come from a checklist of 15 closet must-haves or a guide on modifying your habits so you can look more feminine. It will come from alignment with who God created you to be.

So in your journey to dress more feminine or like a woman, don’t just start with your closet, do the internal work too. If you skip this part you may find that your new found wardrobe may start to feel performative. Like you’re putting on a costume to cosplay the role of someone else who you are not.

Start by asking yourself, “Who am I really when I’m not trying to protect my wounds, impress anyone, or be who the world told me I had to be?”

Then dress her. Boldly and unapologetically. 

Next up: Discovering your version of feminine style

As you embrace dressing in a way that reflects the woman you are becoming, remember that there is no single way to do it. In the next article, we will explore various expressions of feminine style, ranging from soft and romantic to bold and glamorous. This will help you discover what truly resonates with you.

Kesha Dorisma

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