Start With the Easy Stuff

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

When I first started decluttering my clothes, my wife held up an old dress shirt and asked, “Why are you still keeping this?”

It was a fair question. The shirt was two sizes too big because I had lost weight. The collar was yellowing, and the underarms were stained beyond saving. No amount of scrubbing would bring it back to life.

And yet, I had an answer ready: “What if I need it? What if my other shirts wear out? What if an EMP goes off and society collapses, and there are no more white dress shirts anywhere?”

I could hear how ridiculous I sounded even as the words left my mouth.

But here’s the thing: my little brain loves running through worst-case scenarios, stockpiling “just in case” items for situations that will never happen. I suspect I’m not alone in this. We all have that little voice that whispers, But what if we need it someday?

It reminds me of this quote:

My life has been full of terrible misfortunes, most of which never happened.
—Michel de Montaigne

Most of our worries never materialize, yet we prepare for them anyway.

Once I realized I was hoarding this shirt for a doomsday scenario that would never come, I dropped it in the trash. And that small act created momentum.

I went through my closet and dresser, holding up each item and asking, Will I ever wear this again? The answer, more often than not, was no.

And so, piece by piece, I let go.

The Freedom of Less

Afterward, my closet felt lighter. My dresser drawers actually closed without a struggle. And most importantly, I felt an overwhelming sense of relief.

It wasn’t just about space—it was about mental clarity. No longer did I have to sift through piles of clothes I didn’t wear to find the ones I actually liked. The decision fatigue was gone.

If you’re standing in front of your own overflowing closet, wondering where to start, start with the easy stuff.

Here are four simple questions that helped me:

  1. Is this worn out?
  2. Is this not my style?
  3. Will this never fit me?
  4. Am I not excited to wear this?

Let’s break these down with a few examples.

1. Is this worn out?

Some clothes just need to go—no excuses.

For me, this included:

I threw them all in the trash. And while I was at it, I tossed out every old undershirt and pair of underwear and bought fresh replacements.

2. Is this not my style?

Some clothes were in perfect condition, but I never reached for them.

I donated:

And that red hoodie I never wore? My teenage son happily took it. It’s a little big now, but he’ll grow into it.

3. Will this never fit me?

I finally accepted the truth: My closet and dresser are for clothes that fit and are ready to wear.

I donated:

4. Am I not excited to wear this?

Some clothes were technically fine—but if I never reached for them, why was I keeping them?

I donated:

One of those T-shirts was super soft, though, so my son took it. Totally fine by me.

Now It’s Your Turn

That’s the process I followed. No stress, no guilt—just honesty.

So what about you? What’s the easy stuff you could declutter right now?

Start with the obvious: the worn-out, the ill-fitting, the things that make you shrug instead of smile. Let them go. You won’t miss them.

And when you’re done, you’ll wonder why you didn’t do it sooner.

Next steps…