Keep, Toss, Donate, or Sell: A Guide to Cleaning Out Your Closet

by - April 12, 2022

closet cleanout guide

How often do you clean out your closet? I try to go through mine at the start of each new season. I've found it's a good time to assess what I did or did not wear in the season that's ending as well as take stock of what I might need for the upcoming one.

I've recently been doing a major closet cleanout that's been long overdue. I've been holding onto things from my time working in an office because I wasn't sure if I would need them, but it's been four years so it was time to reassess that entire section of my closet. There's also a possibility that we'll be downsizing and moving in the near future, as well, so I knew it was time to start rethinking my wardrobe.

Look, I'll be the first to admit that I have a lot of clothes. I can't even blame it on this blog, if I'm being honest. I like to shop, and I rarely buy pieces that I don't love, so I tend to hold onto things for way longer than I should.

I'm also finding myself in a transitional season of my life. I'm in my mid-30s so my fashion choices are starting to shift and settle into a more consistent style, and a lot of the things I loved in my late 20s that were still in my closet simply don't fit with my current lifestyle.

This maxi dress, however, is certainly not one of those non-conforming pieces. It's easily become my go-to dress choice for this season. It's flattering, easy to wear, easy to accessorize, can be dressed up or down, and the colors are perfect for me.

Here are four simple ways I've styled it.

Dress / Vest (similar) / Shoes / Purse

1. Vest & Platform Sandals - If I've said it once, I've said it 100 times. A denim vest is a must-have spring completer piece. Mine is cropped so it sits at my natural waist to help add structure to the dress without breaking up my body in weird ways. The neutral platform sandals give me a little height boost but don't steal the thunder from the dress.

Dress / Jacket / Shoes (similar)

2. Denim Jacket & Neutral Flats - This is literally the first outfit but with a little bit more coverage. Substitute the vest for a full jacket - quarter-roll the sleeves on warmer days (it was still pretty cool this day) - and the neutral sandals for neutral flats.

Dress / Jacket / Shoes (similar) / Purse (similar)

3. Colored Jacket & Neutral Flat Sandals - I love a good bookended look, and although you can't really see my shoes in this picture, this outfit is perfectly bookended. I chose to do tan instead of a  brighter color, but it's pretty close to the orange-ish colored flowers in the print.

Dress / Sweater (similar) / Shoes

4. Belted with a Colored Cardigan & Matching Flats - This is another bookended look but with a cardigan instead of a jacket. It's a little bit lighter and gives the outfit a sweeter vibe. I chose blue to pull out the blue flowers in the dress's pattern. I also love how simply adding a belt completely changes the look of a maxi dress.

This maxi dress clearly has staying power in my closet. 

✔ It can be worn multiple ways.
✔ It's flattering and fits me properly.
✔ It's in good condition.
✔ It's a classic style.
✔ I genuinely love it.

But it's not the only thing in my closet to check all those boxes. So how do I decide what to keep, what to toss, and what to donate or sell?

Much like when I'm shopping for new pieces, I have a set of questions to help guide me through the process of cleaning out my closet.

Obviously, I can't base everything on whether or not I like a piece of clothing, although that's always my first question to myself. If I stopped there, I'd not get rid of very many things. So, I've developed a system that factors in six key components.

✔ Do I like/love it?
✔ Does it fit well?
✔ Have I worn it in the past year? Six months?
✔ Is it for special occasions?
✔ Is it classic or trendy? Will it still be in style six months from now?
✔ Is it in good condition?

How I answer it each question determines my next question and/or ultimate decision. Is it a completely foolproof system? No. There have been cases in which I've gotten rid of something only to wish a few months later that I still  had access to it, but it's a rare occurrence. Mostly, this series of questions has helped me keep my closet functional without sacrificing my most favorite pieces.

After all, what good is a closet full of so many clothes you'll never wear them all?

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