Several weeks ago, I was talking with a friend about some of the changes women experience as we get older when the word frumpy came up.
I don’t even remember which one of us said it.
What I do remember is that the word stayed with me.
Days later, I was still thinking about it.
Then weeks later, I was still thinking about it.
Why that word?
Of all the words women use to describe themselves, why that one?
The more I thought about it, the more curious I became.
Because frumpy seems to occupy a unique place in our vocabulary.
You know younger women certainly have their own ways of criticizing themselves. If you spend a few minutes scrolling social media—or simply listen to a conversation at the next table in a coffee shop—you’ll hear plenty of words used to describe bodies, outfits, and appearances.
But frumpy rarely seems to be one of them.
That’s a word they tend to save for someone else.
Their mother.
Their grandmother.
The woman they’ve placed in a category they never expect to join.
Which may be why the word lands so heavily when we begin using it about ourselves.
One day, without even realizing it, we hear it come out of our own mouths.
“I feel frumpy.”
And suddenly we’re no longer describing someone else.
We’re describing ourselves.
What’s interesting is that I’ve never met two women who meant exactly the same thing when they used that word.
One woman is talking about weight gain. Another is talking about retirement. Another is standing in front of a closet full of clothes and feeling disconnected from all of them. Still another is struggling to recognize herself in the mirror.
Some women are talking about confidence. Others are talking about comfort. Others are trying to make sense of changes they never expected their bodies—or their lives—to make.
The word is the same. The meaning rarely is.
Which is why I’ve become less interested in the word itself and more interested in what sits underneath it.
A while back, a woman told me during a discovery call that she felt frumpy.
As she talked, I found myself making assumptions about what I was likely to find in her closet. I expected clothes that no longer fit, pieces that were worn out, and a wardrobe that had been neglected for years.
Instead, I found beautiful clothes.
Quality fabrics, thoughtful purchases, and pieces that had clearly been chosen with care.
There was nothing wrong with the clothes.
The problem was harder to identify than that.
The wardrobe still reflected a chapter of her life she had already moved beyond.
The clothes made sense for the woman who bought them.
They just didn’t fully make sense for the woman she was now.
The clothes made sense for the woman who bought them. They just didn’t fully make sense for the woman she was now.
That experience taught me something important.
When a woman tells me she feels frumpy, I know I have some digging to do.
Because the word itself doesn’t tell me very much.
I need to understand what sits underneath it.
What she’s really trying to say.
The more women I work with, the more convinced I am that frumpy isn’t a style category.
It’s a placeholder.
A word we use when we know something feels off but haven’t yet figured out exactly what it is.
I know sometimes the issue is practical.
Our bodies change.
Fit changes.
But often the word points to something deeper.
A woman retires. Her children grow up. A marriage ends. A spouse dies. A health challenge changes how she sees herself. Or maybe life simply gets busy, and somewhere along the way she stops paying attention to herself the way she once did.
We tend to think transformation takes a long time.
Sometimes a single year changes everything.
When life changes, it isn’t unusual for our closets to lag behind.
What concerns me isn’t the word itself.
It’s what often follows it.
I’ve listened to women say it and watched something change almost immediately.
Their shoulders droop.
Their energy shifts.
And before long, they’re explaining why they feel that way.
Nothing looks right anymore.
Getting dressed feels harder than it used to.
Style begins to feel like something meant for a younger version of herself.
It’s almost as though the woman she is today somehow no longer deserves the same attention, care, or consideration.
I’ve seen that look.
Maybe you’ve felt it yourself.
It’s the moment a woman begins to believe that the best version of herself is behind her.
I don’t believe that for a second.
I’ve worked with women who were a size 4 and felt frumpy.
I’ve worked with women who were a size 24 and felt fabulous.
Which tells me something important.
Frumpy isn’t a size.
It’s not a number on a birthday cake either.
If anything, it seems to show up during seasons of transition. Times when life changes and we’re no longer quite sure how to present ourselves to the world—or even to ourselves.
Maybe that’s why the word has stayed with me all these weeks.
The more I think about it, the less interested I am in defining it.
What interests me is understanding it.
Because when a woman tells me she feels frumpy, she’s usually telling me something important.
The challenge is figuring out what that something is.
Here’s what I want you to know.
Once you understand what you’re really trying to say, you’re no longer stuck with a label.
So the next time you hear yourself use that word, don’t stop there.
Get curious.
Are you talking about your clothes?
Your confidence?
Your body?
Your lifestyle?
Your identity?
Are you dressing from habit?
Are you dressing for a life you no longer live?
Or is it something else entirely?
The word may be the same.
But the meaning is uniquely yours.
And once you understand what you’re really trying to say, you can begin to do something about it.
Curiosity is where the real conversation begins.
If this gave you something to think about…
You’ll probably enjoy Outfits & Insights, where I share weekly stories and style observations for women over 50.
I feel frumpy when I wear clothes that are:
The wrong color for me
Too big
Lack structure (unless it’s the weekend and I’m in workout clothes)
Are the wrong fabric