I Cleaned Out 100+ Items From My Closet by Asking This 1 Question

Updated on 4/25/2020 at 12:40 PM

POPSUGAR Photography | Benjamin Stone

You would have never known that I organize and overhaul the wardrobes of clients for a living if you had seen the state of my closet last week. Standing in my closet last Sunday while trying desperately to find something to wear led to the realization that my closet was leading a double life. It's not that it was a "hot mess," organizationally speaking. It was, however, glaringly obvious that everything in there represented my previous life, a very different life from the one I am currently living. A closet filled with four-inch heels and designer duds snagged at countless samples sales (read: I worked at Neiman Marcus corporate for almost a decade and everyone drives everywhere in Dallas) does not a smooth transition to the Bay Area make.

So, I made another cup of coffee, turned on my "Closet Overhaul" Spotify playlist, and did to my own closet what I have done hundreds of times for clients in the past.

I picked up the first hanger and asked the million dollar closet question that works like a charm every time I need to make, or assist a client in making, a decision on what stays and what goes. Two hours and several hangers later, I had over 100 items crammed on a rolling rack ready to donate. Cue: mic drop — and it all started with this question . . .

Does It Serve You?

Sounds simple enough right? Don't be fooled: this question is powerful if you answer honestly.

Here are two ways you can tell if an item hanging in your closet serves you:

1. Does it make you feel good when you wear it? Or, are you excited to wear it? Lukewarm reactions are exactly what you don't want here. Let it go. Try it on if you need to, and, even better, have an honest friend (the one you always bring into the fitting room with you) there to give you honest feedback when you get stuck.

2. Do you actually wear the item in question? When is the last time you wore it? If it's just taking up space and you can't remember the last time you put it on (if ever), it's time to part ways. Anything with tags still hanging on it, dust collecting on its shoulders, or waiting in the "way back" because you swear you will lose those extra ten pounds is what I'm referring to here. If it falls into those categories, it serves no purpose. Let it go.

Here is a picture of my closet before the clean out. Sure, it wasn't super messy or ridiculously overcrowded, but over half of the contents didn't fit my current life.

Case in point: check out my shoe situation. Note the number of heels in there. I can safely say my shoe collection is 90:10, heels to flats. Read: not San Francisco-friendly.

Now take a quick peek at what my closet looked like after just two hours.

The shoes were reorganized and spaced out now that I made room on those shelves. Love. That.

I know what you're thinking: "It kind of looks the same!"

Well, I didn't take too many close-ups, but you're about to see where the major change happened.

Everything on the rolling rack from my closet that day, plus nine pairs of shoes and one large garbage bag (overflow), has been cleaned out.
There are over 100 pieces that will now be either donated or sold.

If you start freaking out about letting go of something, do this: hang the items in question on the front of your closet. Get a sticky note (I use these hang-tags so nothing falls off) and pick a date four weeks out.

Hang a tag on each item. If you don't wear that item between now and that date at least once, I can safely say you won't wear it at all within the next year. Translation: that item no longer serves you and it is time to let it go. If you do wear it now that you can see it (which is sometimes half the battle), once or even twice, and feel good wearing it, then the item stays.

When you remove the clutter, you can start to see what you have. You'd be amazed at how many outfits you can make with fewer items hanging in your closet.

After I help my clients remove clutter from their closets, they tend to look at the donation pile (mountain) and then back at me with fear in their eyes. They're seeing only what they're getting rid of, not what they are gaining. This is the perfect time for my favorite part of the entire process, when I go back into their streamlined closet and create 20 new looks they never saw before using less clothing than they originally had. These outfits were there all the time; they just couldn't see them.

Now, imagine the pieces hiding in your closet. It just takes asking one question to find out . . .