I've been slowly decluttering a few items here and there, but for my personality, I'm thinking that one giant purge over the weekend and quitting shopping cold turkey will be the most effective and impactful to snap myself out of my over-shopping habits and to stop buying things I don't need.

To start, I was thinking of going through my closet to begin with any recent purchases that I can still return and take back to the store. However, I'm having a hard time moving past those aspirational items and also some deeply discounted items I scooped up on sale that are arguably "staple" items that will have longevity, for example, an amazing leather jacket (I've never owned a leather jacket). But, if I'm being honest, how often will I actually wear a leather jacket given my casual, athleisure lifestyle and hobbies?

Objectively, and from what I've read and learned from all the decluttering gurus and minimalism advocates, I know that once the items are gone, it will be such a weight off my shoulders, and I'm confident that I will relish in having only my favorite and functional items in my closet.

I'm tired of living with an over packed and chaotic closet. Sometimes I'm trying to rush out the door and I can't find or can't get to the one thing I need in the back of my closet. How do you get past that first hurdle to do such a monumental project? Thanks in advance for any advice!

TLDR: Want to stop shopping and do a massive clothes declutter. Having a hard time letting go of aspirational items that I don't need, especially great bargain finds. Closet is out of control. Help!

Wanted to share a bit of joy I experienced today.
My family made up several boxes of clothes to keep in case we “managed to fit into one day.” It’s been almost a year and nothing has changed.
Today we decided to take the boxes to our local church run thrift store. As I unloaded the boxes with the volunteers, they immediately started to dig in to begin sorting and pricing. Dropping off the last box, I noticed they were really looking at them.
“That is so cute.” “Oh my goodness, is that your size?” “That looks like the jacket you’ve been eyeing.” “Think this goes well with my jeans?”
It made me feel good about donating since they were really enjoying the clothing and were setting aside items for themselves. It was great to see people actually want these items and making real plans to wear them. Plus they’re volunteers at a thrift store where all revenue goes toward education projects so they deserve something nice.

My lesson of the day: donate what you have lingering because it just may be exactly what someone else is looking for.

I want to become better at decluttering in the moment, every day. My lifetime habit has been to let things build up and then do a BIG declutter. I’m getting older and do not want the big build up anymore.

My question is for those who are GOOD at making decisions in the moment and keeping clutter at bay by never letting it build up. What do you ask/tell yourself? How do you avoid regret? How do certain things make the cut?

Examples are: junk drawer items, worn out clothing, cosmetics I’ve had awhile, school related stuff…but truly anything and everything.

I envy people who look at something and say, “I don’t like this.” And into the trash it goes. I feel so guilty! I’m big on donating but I think it’s becoming an excuse to let things build up.

I don’t want to have to move piles/car loads all at once. How do I become a better daily declutter-er?