How a Professional Organizer Fixed My Messy Closet (and Changed My Life)

Clothes tell the stories of our lives. A few months ago, I had over two decades of dresses, pants, jeans, sweaters, and blouses in my closet, and each piece held a memory: a black shift dress that was my go-to for cocktail parties and, when paired with a blazer, job interviews in my 20s. A double-breasted, ankle-length camel coat from one of my annual fall shopping excursions with my Grandma Lenora.

I don’t like goodbyes, and I wasn’t good at parting with clothes. What if that style comes back? (It happens!) And that was a gift from Grandma L; giving it away would feel like letting go of that memory. Over the years, my closet got more and more stuffed—so much so that getting dressed would sometimes turn into a take-everything-out-and-toss-it-on-the-bed-to-find-that-V-neck-sweater ordeal.

But every time my husband would say, “Amy, let’s clean out,” I would get a knot in my stomach. I wasn’t sure how to turn this into a neat, color-coordinated space. Then I met Rachel Rosenthal, an organizing expert who felt my pain and had a plan—along with plenty of empathy and insight. Here’s how she helped me conquer the clutter. 

1. Be Compassionate with Yourself

Giving things away and getting organized have an emotional component that can be a stumbling block. And when a project feels too overwhelming to tackle, it can seem like you’ve failed. “It’s hard not to tie our sense of success and worth to how ‘together’ our spaces appear,” Rosenthal says. “Getting organized is an ongoing tool to make things easier. Give yourself grace as you navigate the process; how organized you are isn’t a reflection of your value or capabilities.” 

2. Sort Smart

As you’re going through your clothes, ask: When was the last time I wore this? Was it within the past year? If not, why? Do I love this piece? Do I feel good wearing it? For me, this was the cornerstone of the process, since I had two decades of clothing to sort through. Why was I holding on to all of it?

As Rosenthal held up each skirt or dress, I often thought, Wow, that’s baggy, and I realized how my body image had changed over the years. So many of my old clothes hid my figure, while wrap dresses and skinny jeans that embrace my curves are now my staples.

3. Think About Your Space and Habits

“True organization isn’t about everything being color-coordinated,” Rosenthal says. (Whew.) “It’s about creating systems that work for you.” My closet is narrow and has many high shelves that are hard for me to reach, as I’m 5’1″. Shoes covered the floor, so I couldn’t stand inside the space and really see what I had.

Solution: Everyday shoes were moved to the reachable shelves, while items that I wore infrequently were placed in bins on high shelves. 

4. Put Clothes Back with Purpose

Rosenthal helped me realize there’s no one-size-fits-all way to arrange your clothes. The key to a system that works is thinking about your routines and the way you put together outfits. The clothes you wear most often should be the easiest to access.

We hung dresses, blouses, and jumpsuits front and center; jeans and pants went from hanging to folded on shelves with dividers so the entire pile wouldn’t come cascading down when I took out one. This created room to hang belts and zip-up jackets, which I wear every day but were crammed in drawers. That simple switch probably saves me 10 minutes of searching—and stressing—daily.

I’m happy to report that my closet still looks like the “after” photo. Did I get rid of everything I haven’t worn in the past year? No—and that’s OK. Sentimental reasons can be enough to keep something. That camel coat from Grandma L is tucked into a garment bag out of the way until I want to wear it or just put it on to remember her. 

After eight hours with organizer Rachel Rosenthal, I had 20(!) bags of unneeded clothes. I gave them to Dress for Success, which helps women entering the workforce, and a local Goodwill.