4 Ways to Ask, “Do I Actually Want This Item?”

This is part of Stewie's Guide to Ruthlessly Declutter Your Clothes Today.

My wife and I are both the oldest siblings in our families, which means we’ve attended more than our fair share of weddings. Between the two of us, we have 11 siblings, and over the years, that’s meant a rotating door of invitations and formal celebrations.

With each wedding came another outfit—slacks, ties, and dress shirts that matched a carefully coordinated family color scheme.

In addition, both of our families like to have family photos. (You know, the kind where everyone has coordinating sweaters that make you itch all over?)

So, year after year, I’d buy clothes, wear them once, then shove them into the back of my closet, where they’d never see daylight again.

Now, logically, these should have been the easiest clothes to part with. I never wore them. They served no real purpose. And yet, I struggled.

Because here’s the thing: I come from a long line of packrats. Holding onto things is practically a family tradition. And letting go? Well, that’s never come naturally to me.

But at some point, I realized I didn’t want to be someone who kept things out of guilt or habit. I wanted a closet that actually worked for me, not one stuffed with clothes from past obligations.

So, I started asking myself a few key questions.

1. Would I pay $1 to keep this item?

I’ll admit it—I love a good deal. My little brain is wired to save money, which means I sometimes keep things just because I already own them.

The problem? Just because something was a “good deal” doesn’t mean it’s a good fit.

So, I flipped my thinking. I stopped asking, “Should I keep this?” Instead, I asked, “Would I pay $1 to keep this for another year?”

Suddenly, decisions became crystal clear. Would I pay $1 to keep an ill-fitting dress shirt? Nope. What about those uncomfortable slacks from a wedding five years ago? Not a chance.

It was strangely liberating. Instead of clinging to things because they were already mine, I started choosing what was truly worth keeping.

(This method works wonders for clothes you hang in your closet. Not so much for socks and underwear—but we’ll get to those.)

2. If I had to evacuate in three hours, what clothes would I pack?

A few months ago, wildfires ravaged Southern California. I remember seeing the images of the sky, thick with smoke, and all of those homes lost. It was heartbreaking.

And it got me thinking, if I had only three hours to evacuate, what clothes would I grab?

Not the ones that were just “okay.” Not the ones I kept for “just in case” occasions that never actually happened. No, I’d take the clothes I love wearing—the comfortable, reliable ones I reach for every day.

So why was I letting the rest take up space in my closet?

Another version of this question: “If I had to pay movers to box up my wardrobe and move it across the country, what would I keep? What would I donate?”

Suddenly, I saw things differently. That sweater I had kept just because of a family photo? Gone. The extra socks stuffed in the back of the drawer? Donated. The idea that I should keep something simply because I already owned it? Out the window.

3. Will I commit to wearing this next week?

I used to hold onto clothes for future versions of myself—the one who would, surely, one day, wake up and suddenly love sweaters. (Spoiler: That day never came.)

So, I started getting practical. I asked, “Will I commit to wearing this in the next seven days?”

Not “Could I?” or “Should I?” but will I actually wear it?

If the answer was no, why was I keeping it?

For seasonal clothes, I stretched the timeframe. “Will I wear this winter coat before May 1?” If not, then donate it.

4. Would I buy this again?

This was a game-changer.

If I saw this shirt, jacket, or hat in a store today at full price, would I buy it again?

Would I rush home, excited to wear it? Or would I hesitate, trying to justify the purchase?

If I wouldn’t buy it again, I had no business keeping it.

This question helped me let go of things I had been settling for—clothes that were just “fine” but never made me feel great. And honestly? My closet and my mindset are better for it.

Decluttering That Finally Made Sense

These four questions helped me let go of guilt, break free from old habits, and finally curate a closet that feels like mine.

The $1 question was the most effective because I’m motivated by money (yes, this probably says something about my childhood, but let’s not go down that rabbit hole).

But that’s just me.

Try them all. See which ones click for you. And then, start asking yourself, “What am I ready to let go of?”

Because the truth is, your best clothes aren’t just the ones you own—they’re the ones you actually wear and love.

Next steps…