Keep or Toss? The Gumshoe Guide to Cleaning Out Your Closet

7 questions to ask yourself next time you're paring down.

I get a lot of satisfaction from cleaning out my closet. I try to live by the philosophy that it isn’t a museum, nor is it a time capsule of my personal style evolution (that’s what my camera roll is for!), and make a conscious effort to clean it out on a regular basis. Over the years, I’ve actually found this process to be one of the most effective tools I have for honing my sense of personal style. Not only does it clear out space, but it’s also an opportunity to remind myself what I’m really drawn to and why, and gives me an even deeper appreciation for the things I choose to hang onto. In today’s newsletter, I thought it might be helpful to share some of the questions I often consider when deciding what to keep, sell, or donate to goodwill — with the goal of being as intentional as possible throughout the process.

Cher surveying the contents of her closet in Clueless

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1. If this disappeared, would I notice within days?

There are certain pieces that will trigger an obvious and unequivocal yes – i.e. the stuff I wear on a weekly basis. A sentimental or special occasion-type piece is usually the trickiest thing to purge because it might be less relevant to day-to-day dressing, but I can always concoct a hypothetical scenario in my head for which it might come in handy, or an emotional reason to hang onto it. That’s why this question is such an important one. It goes beyond “do I like this?” or “do I wear this?” and ratchets up the stakes to: “Would its absence set off a panicky alarm bell in my head?”

2. Does this make me feel good, both physically and emotionally?

There’s a vast difference between pieces that sit beautifully on my body and make me feel like my best and most confident self, and pieces that make me feel self-conscious, or that I’m constantly adjusting. It’s helpful to think about where things fall along that spectrum. If I love the idea of a piece but feel off every time I put it on, or if it’s something that used to suit the shape of my life but now feels like something I’ve outgrown, then I’m probably just hanging onto it out of habit.

3. Is this high-quality?

I’ve pretty much entirely purged my closet from synthetics over the years by asking myself this question. I’m increasingly reluctant to devote valuable wardrobe real estate to things that feel flimsy, wrinkle easily, and hang awkwardly. I’d rather prioritize space for pieces that are a pleasure to wear, made to last, and have thoughtful details that set them apart.

4. Is this in good condition?

If an item is damaged but not irreparable and I’ve still been procrastinating dealing with it — that tells me something about how important that thing really is to me, and to the way I get dressed. 

5. Can I style this in more than one way?

I always think through the number of outfits I can build around a certain piece, and whether it works for multiple occasions or seasons. Chameleon pieces that can be layered, dressed up, or down, and worn across different settings are much likelier to survive a clean-out. 

6. Are there outfits I love wearing that depend on this piece?

I also try to consider not just how much I like a certain piece, but also how hard it’s actually working in my wardrobe. It’s interesting to note when I’m not necessarily obsessed with an individual piece as a standalone item, but it happens to be integral to a number of my favorite outfits. Conversely, sometimes I have a positive impression of a certain piece on its own but it’s consistently very tricky to style. The latter is something I’m less likely to keep, in the long run.

7. Is it evergreen?

One key lesson I've learned from regular closet clean-outs is how quickly trend-driven pieces tend to lose their appeal. They often start to feel fraudulent, more like a gimmick than an organic feature of my style. When purging, I focus on distinguishing between pieces I’ve consistently connected with over the years versus those that feel like outdated relics or temporary whims.

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How I Interpret My Answers:

Mostly “Yes” Answers:
The piece deserves to stay.

Mostly “No” Answers:
It’s not working hard for me, and it’s taking up valuable space in my closet. Time to let it go.

Mixed Answers:
Hmm. If I’m on the fence, I ask myself what needs to change for more answers to be “yes.” Is that change even possible? If not, I’m probably just delaying the inevitable. 

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What strategies do you find helpful when editing your closet? Is it something you get satisfaction out of, or a dreaded chore? I’m curious to hear.

xo Harling