Challenging myself to wear the same dress for 100 days straight, I’ve had ups and downs. Many days I wonder why I’m doing this. I made a commitment to sustainability at the start. But sustainability alone has not been enough to keep me inspired (translation: staying on the rails). TBH, I’m getting tired of having to wear it or style it some sort of way every single day.

You do you, dress wrinkles and all, has been the conventional wisdom. But going throughout the day, wrinkled inside and out, feels even more unappealing.

A couple of days ago, I received some advice that I’ve been mulling over non-stop: Dress for the day you want to have.

The woman offered the advice half-apologetically, calling it a cliche.

But I had never heard this expression before, only some variation about dressing for the job you want and not the job you have.

Dress for the day you want to have is different. It’s insightful. Helpful. Actionable. And just feels powerful. It shifts the paradigm from chasing the unattainable to ways I can elevate the everyday.

We buy clothes for the life we want to have. That gorgeous, elegant woman sipping tea on a botanical terrace. Draped across a mosaic-tiled folding chair. Wearing a floor-length silk slip dress, layered with an oversized black lambswool sweater. Big gold hoops. And hair, in a loose low ponytail at the nape, gently blowing in the breeze.

I. Want. That. Outfit. I’ve wanted it for several months, ever since I first saw it on the Banana Republic website.

“I want that dress; I just don’t know where I’d wear it.”

That’s why I never pulled the trigger on the silk gown.

And this is a common lament I overhear when I’m at the Galleria (on a monthly pilgrimage to get my roots colored).

“Buy it anyway!” we urge, or are urged. Because the dress is so “cute” or “such a good deal” or perfect for this upcoming one-time event. Or we’ll “just wear it all the time” because we love it so much.

The latter never happens. At least not for me. I think it’s because the clothing we buy is aspirational. We buy it based on marketing imagery. We buy for the life we want to lead, and not for our day-to-day grind.

So I can’t buy that silk maxi dress. Quite literally. Banana Republic follows a fast-fashion calendar when releasing new styles. Multiple fashion drops within every season, and old drops getting clearanced into oblivion.

And I can’t buy that silk maxi dress because it does not match my life. I don’t drink tea. I don’t wear earrings. I don’t do dry cleaning. And I definitely don’t lounge on terraces. I’d settle for a nap in a semi-clean home with most of the toys off the floor.

Realistically, when I envision clothes to confidently live the life I do lead I see a closet of very different clothes than the images I covet on Instagram. I see a drapey wool sweater with a cowl neck and kick pleats, a twill chore jacket, a boxy oversized cardigan, paper bag waist jeans, a maxi dress that can go anywhere, and a few organic cotton tees. (Related: Why does my shirt have to be organic if I’m not going to eat it?)

My life is not comprised of cashmere dress or mini skirt moments, and buying these garments cannot will them into existence.

The Disconnect Between What’s in Our Closets and How We Live Our Lives

I don’t think I’m alone in this dissonance. What’s in our closets doesn’t reflect the daily lives we live. It reflects the lives we want to live when. Or at least the lives we thought we wanted to live when we were feeling impulsive (or motivated) enough to buy the outfit.

On-trend fashion is hyper-affordable and everywhere making it possible for us to chase the endless pursuit of style. We’ve got a closet of clothing but nothing (we want) to wear. There’s always one more cute garment to make us complete. Even with wardrobe classics.

My closet has, for instance, lots of fashion staples I don’t wear. Crewneck cashmere sweaters I bought because they’re supposedly a cornerstone in every woman’s wardrobe that will get lots of wear for years. A strand of pearls. Long maxi dresses and maxi skirts – because they can go with anything (yet get worn with nothing). And lots of denim. I like the jeans I have — until I see nicer jeans on a nicer version of myself.

So before the dress challenge, I would find myself opting for jeans and a tee. Or the same gingham print maxi dress (Old Navy) that I do adore. Amid the sea of choices, that’s what I would settle on. Whether it was the overwhelm (turns out that word is a noun) or the apathy, I’m not sure.

Of course when having a really good hair day, I would feel uplifted enough to select a more stylish, under-worn garment. But that happened a handful of days each month. Then, I would feel optimistic, upbeat, and inspired. And write – about fashion – trendy toddler styles and brand reviews and the crazy world of buying and selling used clothes. (Related: What’s a Buy Sell Trade Group?)

When I’ve settled on jeans I don’t quite love and a tee that will have to work, I don’t feel invested in myself.

Most days, I was getting out of bed and dress myself in blah clothing for a blah day. Blah. That’s the intention I set for myself.

Dress for the Day I Want to Have (Not the Life I Want to Have)

I’ve decided to start dressing for the day that I want to have. Not in a fake-it-til-you-make-it sort of way. But in an honest way.

I’ve realized that how we dress each morning sets the intention for the day we want to have.

Even wearing the same purple dress every day, I can adapt my outfit to the outlook I want. Clothing and mood are, for me, inseparable.

Yesterday, I got out of bed wondering what would really happen to my teeth if I didn’t brush them that day. And I debated making the bed. (Bed-making was supposed to become an automatic habit after 40 days, yet’s it a daily morning exercise in mental gymnastics.)

But yesterday I got up. Made the bed. Then asked myself, “What kind of day do I want to have?”

Orderly, productive, and reasonably tidy was the answer I came up with. A day focused on being productive at work and also feeling productive too.

What does an orderly, productive, reasonably tidy person look like? That’s the question I answered as I got dressed.

Do I want to take the time to comb my hair and put on lip balm? Or shove my hair into a messy bun. I chose the former, and my day was the better for it. I don’t think I’m capable of dressing messy and having a well-ordered day.

I also put on a pair of my favorite dark indigo jeans. And made a to-do list of what I wanted to accomplish at work that day, and I crossed over 80% of the items off my list. I didn’t feel especially pretty or stylish. I felt solid. Capable. Purposeful.

When did it become OK to not be OK?

I discuss this idea frequently with my shrink. When did it become OK to not be OK, in terms of physical appearance?

I don’t mean this as a judgment on anyone’s personal style or mental health; I mean it more in terms of historical context. When I was in high school and college, there were days when I went to school in pajama bottoms and a hoodie. Other students too.

But I know that no one in my parents’ generation did that during high school and college. So there was a shift within one generation where pajama pants in public spaces became normal. How? Why?

Also, there are many days when I am disheveled. My hair isn’t combed. My glasses are smudged. I’m not wearing SPF on my face. I’m wearing a faded tee that has small holes near its hemline. And there’s nothing particularly remarkable about my scruffy appearance as I run errands at Target and go about my day.

Maybe it’s because I feel like I mirror many other women in my peer group. It’s become common to not brush one’s hair and wear rumpled clothing we don’t feel good in.

I think it’s to do with a broader message of self-care: we need to give ourselves grace and not worry about what other people think or what society thinks is beautiful. Inner beauty comes from within and it’s ok to not look like an Influencer or a fashion model. It’s ok to not have the energy (the spoons) to worry about style and looking put together.

All of those things are true: self-care and inner beauty are more important than chasing the latest fashion trends or being impeccably made up each day. I have a job. Spouse. Kids. Home. Plenty of more important things to command my energy. But somehow, getting dressed and presenting myself has become an all-or-nothing equation.

When did lack-of-care become self-care?

It feels like lack-of-care has become a form of self-care. Roll out of bed and roll with it. A faded shirt I don’t feel good in? It’s ok to not be ok. Sagging pants with missing drawstrings? Greasy hair roots? I’m not on Tinder, who cares. It’s just me. I don’t need to be frivolous (anymore).

Either I step out looking well-groomed, well-heeled, and stylish with my face made up and my hair blown out. Or, I step out in mussed clothing and unkempt hair. (Large tangles shoved into a bun.) Those are two very large extremes.

On disheveled days, it feels, for me, like giving up. Like I don’t have the ability to project the image I want (maybe I don’t even know what that image is), so f-ck it. And when I step out into my day, not feeling good about how I’m groomed and with a fatalist, all-or-nothing attitude, I’m probably setting myself up to have a f-ck it all kind of day.

Of course, it is possible to not be concerned about fashion or clothing. There’s nothing wrong with that. (In fact, I find that enviable.) But I think there’s a difference between daily grooming vs a desire to be fashionable. For me, the two very much go hand and hand.

When I pick up the kids at daycare, I’m wearing my mom uniform: dirty flip-flop sandals and messy hair. It’s not a deliberate intention where I choose to not wipe the smudge off my sandals or comb my hair so I can invest the energy into another form of self-care. It’s me deciding that I / It / They don’t matter. So who cares.

And yet, I have to believe I myself am worth investing in and that I deserve to take care of myself even when I’m not feeling stylish or attractive: that means some very basic, daily grooming that I don’t always (want to) do. This looks different for everyone, but for me, I think this means combing my hair. Washing my face. Putting on tinted moisturizer (with SPF). And wearing clean, matching, non-rumpled clothing that can carry me through the day’s tasks. It’s about daily intentionality. I don’t think I can have an organized day if I can’t take 3 minutes to organize my hair.

I think daily grooming is personal care, and I don’t know if lack of personal care can be a form of self care.

100 Days of Intentional Dressing

Maybe that’s a part of the reason why the Wooland 100-Day Dress Challenge is so alluring. There’s an intention you’re setting every day around whatever goal you have tied to the challenge. Maybe it’s finding a creative way to style your core garment. Or leaning into slow fashion sustainability. Or maybe it’s survival, as in just making it through the day. (For some people, their whole intention behind the challenge is to never have to think about what they’re wearing. And they’re baffled at the depths I have pondered the dress.)

I think I’ve discovered that my Clara dress isn’t an intention in and of itself. It’s an extension of myself. And I need to think about the day I want to have every morning, and dress myself – and the dress – accordingly. The dress itself isn’t transformational; it’s how I approach it.

I can have a bad day. I can approach it with that intent. I can decide today is a day I’m going to grieve a particular loss or life trouble. And wear pajama pants all day. And sit in bed and eat ice cream. But I think it’s a more common occurrence rooted in apathy vs an occasion I connect to a particular trauma.

I Feel Pretty

And really, I just want to feel pretty. Who doesn’t? When I feel put-together and pretty, I feel confident. And powerful. Maybe it’s how I’ve been socialized as a woman.

I’ve been focusing on being polished (mostly) every day wearing my wool Clara dress. Because it’s either spit and polish and pretty. Or wrinkles and apathy. Those are the two polar images I see. Those are the two choices I know.

But there’s a lot of in-between that I want to explore.

My 100 day Clara dress is versatile enough for this exploration. Out of this dress, I can get a blouse, a tunic, or a dress. With accessories, I have a garment I can wear on bike rides, hikes, fancy restaurant dinners, or a symphony concert. It’s got major Barbiecore energy and practical versatility.

It’s a dress for the life I live, and, I suspect, the life I want to grow into.