One question that makes decluttering easier

It’s helped me let go of so much

Decluttering can be tricky. We all start with good intentions, but inevitably, we come across something that makes us wonder if we’ll regret letting it go, even though we haven’t touched it in years. Maybe even decades!

Here’s what I ask myself when that happens:

Would I buy this again today?

This question was a game-changer when I did my first major wardrobe declutter back in 2018. Our kids were two and twelve weeks old. We were living in the mountains of Central Oregon, and I was squeezing in freelance writing and food photography between playground meetups, nap times, and almost daily doctor visits.

Yet my closet was still full of dresses, blazers, and blouses from our newlywed years in San Francisco—days that were more about office meetings and happy hours than spit-up and diaper changes.

Asking, “Would I buy this again today?” helped me recognize when I was holding onto clothes out of guilt, nostalgia, or “just in case.”

What if I went back to an office job? (I never did.)

What if I fancied a silk blouse for a night out? (Never happened!)

If I’m being honest, most of those clothes didn’t serve any purpose in my life then—and they still don’t, even seven years later. I’m so glad I let (most of) them go.

If you ever feel stuck, ask yourself, “Would I buy this again today?” If it helps you let go of something, come back and leave a comment—I’d love to hear about it.