I grew up with the good fortune of having an older, stylish cousin whose clothes were regularly handed down to me. At least once a year, a bag of clothing would appear — all new to me, from “cool” brands — and I would divide them between myself and my sister. I felt lucky to have these clothes, and it wasn’t really much of a compromise: They were all in good condition, still in style, and fit me, too. But it wasn’t until recently that I realized I’d made very few decisions about my own closet over the years. At some point, it became a mishmash of things handed down, thrifted, and occasionally bought new, but without much direction.
“It wasn’t until recently that I realized I’d made very few decisions about my own closet over the years.”
In that sense, my closet tells a familiar story. Many of us look back at our childhood or even teenage wardrobes and think, What were we thinking? But beyond questionable style choices, there’s another layer — the way our early habits around clothes can linger. For me, it shows up as an inability to let things go.
Growing up, my mom often mentioned a kind of apocryphal pair of riding boots from her teen years in the 1970s. Beloved by her at the time and lost to history, she’d often say: “I wish I’d kept those boots to give to you.” That refrain stuck with me. Somewhere along the way, it planted the idea that I should hold onto everything — just in case some future generation might want it, even if I wasn’t sure that generation would ever exist or appreciate my things.
As it turns out, my calves rarely accommodate a knee-high boot. So the riding boots were never meant for me, anyway. Lately, I started thinking: Forget these ghosts of the future and past — the shirts I’ve been handed down (don’t worry, there’s a pile for sentimental items) and the shoes that don’t quite fit but feel valuable for some reason. It’s time to start dressing for me. 👗
A stylish encounter
When I happened to meet Áine Hegarty, I thought: Maybe she can help. Every closet cleanout in the past few years has left me feeling stranded in the same place. Every strategic purchase seemed to quickly be added to the list of items that didn’t exactly work as I’d pictured. (For instance, the not-inexpensive belt that I bought to fill a hole in my wardrobe that ended up rubbing off black dye behind the belt loops of all of my pants, especially the white ones.)
“Every closet cleanout in the past few years has left me feeling stranded in the same place.”
I needed a method, an expert, who could help. I was working without a compass, and it was not serving me. Áine did not disappoint, though I may have fallen ill in the middle of our session. (At the time, I thought it was just exhausting to clean out one’s closet and make so many decisions — that I would have to include this detail in my essay so readers could beware — but it turns out, I had the common cold that everyone in Brooklyn was coming down with in early October.)
Áine’s worked as a stylist for years. What I loved hearing was that she was also someone who naturally cleaned out her own closet regularly. With dollops of wisdom from Marie Kondo and practical wisdom from working with clothes and models on sets, we set out to pare back my closet to the things I loved.
How we cleaned out my closet (and how to replicate it at home)
If you’re someone who regularly gets rid of clothing items, you can skip to the next section. But if you currently have your old talent show costume hanging next to a fancy dress you wore to a wedding three years ago, then stick with me while I take you through the closet cleanout process.
The method? Piles.
Don’t get too tripped up in defining the piles before you start making them. We started by taking all of my clothing out of my closet — starting with the tops, bottoms, and casual dresses that I had hanging. This is where I go to get dressed each morning, so this section was our primary focus. As we began sorting, the need for certain piles revealed itself. You might find yourself with other, different piles, but here’s what we ended up with:
- Consistently wears and likes (keep)
- Never wears, or wears but doesn’t like (sell or donate)
- Doesn’t fit, but I love it (alter)
- I like the idea of it, but not how it actually is (consider purchasing a replacement)
- I’m keeping for sentimental reasons (store away from everyday items)
- I wear this for special occasions (store away from everyday items)
- It’s a seasonal piece (store away from everyday items)
If I struggled to decide which pile an item should go in, Áine would remind me that we would revisit the piles again at the end, so no decision was final. (Ultimately, I didn’t change any of my decisions — and it may be thanks to this safeguard, which sufficiently allowed me to explore how I really felt about each item.)
I was surprisingly left with no regrets when the process was over, which I credit to the conversations that Áine and I had. If I was on the fence about something, we discussed what I did or didn’t like about it. Sometimes it would go in the needs-altered pile, or tentatively to the give-away pile, based on my reasoning. If something had sentimental value but I didn’t actually wear it regularly, it went into its own pile alongside my nana’s nightgowns.
How to construct new outfits from old favorites
Once your piles are in a good place, it’s time to get creative with the “Consistently wears and likes.” The truth is, I had about 30% of the shirts I started with when we were done! It struck fear in my heart, until I saw how many outfits were possible with just the items I really loved. Wearing them over and over is what I like to do, anyway! And with no shortage of inventive combinations to play off of, my pile for selling and donating began to feel like a final answer.
For the second phase of this process, choose four tops you love, four bottoms you love, and start playing around with how they pair. Pull in a few favorite pairs of shoes, a sweater or two for layering, and a favorite statement necklace to add some dimension. I found that pulling different pieces together in this way, based on their colors and silhouettes, led us to unexpected places. Time after time, Áine would put something together that was totally novel and yet made complete sense.
Since our appointment, I’ve worn many of the outfits she put together. But even more so, I’ve found myself experimenting within the parameters she laid out around what makes an outfit feel like an Outfit and not just clothes.
Her two simple rules:
- Look for contrast in styles: If you have a menswear shirt, pair it with a ballerina flat. A romantic blouse might pair perfectly with a structured bottom. You get the idea! It’s shocking how well this works.
- Aim to incorporate three different textures: Whether this is with a sweater around the waist, a leather belt, or adding in costume jewelry over a silky blouse, notice the materials that make up what you’re wearing and aim to add a third! Pro tip: When you add a sweater around the shoulders or the waist, don’t be afraid to play with positioning it slightly askew for more interest and a better silhouette. You’d be shocked at how well this works, too!
How to organize your closet — and what comes next
The real goal of this whole process is to create a functional, organized closet. As Áine advised me, sorting through a decade of memories, damaged items, and pieces from the wrong season each time you get dressed just adds unnecessary mental load. When I was honest with myself, I was only wearing about 5–6 tops and bottoms regularly anyway — so what was all this stuff?
“Sorting through a decade of memories, damaged items, and pieces from the wrong season each time you get dressed just adds unnecessary mental load.”
The practical advice here is to keep your sentimental, seasonal, and special items in a separate place for safe keeping. Just because they’re in a drawer doesn’t mean you love them any less — but it will allow you to get dressed in a smart way, rather than getting lost in the sauce. As for further organization, consider grouping items by their type: Knits, blouses, cotton tee shirts, can take up residency in groups. That way, when you’re aiming to incorporate three different textures, you can easily execute. Overachievers might also want to group by color. (You’ll have to tell me how that works for you. 😉)
In the days following this process, Áine encouraged me to notice how I was getting dressed, take selfies of my outfits, and see if there were any pieces that I felt were missing. I kept the pile of items for donations and resale closeby incase I might have made a misstep. But, that moment never came. I felt that my closet was full — actually, more full than ever — with items that I loved. I had more than enough.
Ashley D’Arcy is the Senior Editor at The Good Trade. She holds an MA in Philosophy from The New School for Social Research and has contributed to esteemed outlets such as The Nation, 032c, and Yale School of Management’s Insights where she’s leveraged her expertise in making complex ideas accessible to a broad audience. In addition to her editorial work, she is training as a psychoanalytic mental health professional and provides care to patients in New York City. Ashley also explores sustainable fashion, clean beauty, and wellness trends, combining thoughtful cultural critiques with a commitment to mindful living.
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