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The Summer Closet Clean Out – Part Two

We ended last week with the start of our Summer Closet Clean Out Series, giving you the weekend to wrap your arms around the process.

Getting started can feel daunting but having a plan and strategy will help with the overwhelm.

I spent a couple hours over the weekend going through everything I own.

Since I’m fresh off the process, I thought it would be helpful to share some behind the scenes photos, and the real time ridiculous thoughts and struggles I had along the way.

Remember it always looks worse, before it gets better.

During: A Mess

Now that I’m done, I really do feel lighter.

Everything is back in it’s place, I moved some things around to optimize my space, and, as always, I found pieces I forgot about and discovered a few new outfit combinations.

Today we’re breaking down the messy middle, the part the even makes me want to shove everything back in my closet and deal with it later, or never.

The middle is what I call the “Ruthless Edit,” where you have to hold your feet to the fire and make tough, uncomfortable decisions.

And, this might sound silly, but it brings up a lot, so let’s get into it.

If you haven’t already, work through part one.

Part one is designed to specifically to make part two easier.

So if you have gone through all the steps up to now, you have what we call the “maybes” pile – the pieces in your wardrobe that you don’t know if you should keep or toss.

Keep or Toss

Let’s talk quickly about the decision making process with some real life examples.


I love this pretty lace short sleeve top from Express that I bought last year.

It fits me well, it a perfect style match, I can wear it a few different ways and every time I put it on I feel great.

This is how simple a keeper should be.


These jeans served me well.

I got a lot of wear out of them but (happily) they are too big and they are not worth altering.

So they go in the toss pile.

They are in excellent condition so I am sending them to Thred Up for resell (more on this below).

An easy toss.

What to do with the Maybes

The Maybes are buggers.

They complicate the process of getting dressed, burn mental energy we don’t have, and in some ways seduce us into thinking our life is something it isn’t.

Before you dive into them make sure you are in the mood to deal with them, and have a crystal-clear understanding of you life and personal style.

Take your pile, and one by one ask yourself, does it fit, do I love it, will I wear it, is it my style?

Here’s an example from my own edit.

Maybe – Keep

Because I couldn’t make a quick decision about this Banana Republic blouse, I put it in the Maybe pile.

And then I stopped and came back to it a few days later.

Here’s the deal.

I do really like this.

It fits well, and the color is pretty.

It’s a little formal for my lifestyle, which is why I haven’t worn it since last year. And I only wore it once.

I decided to keep it, because every now and then I need a blouse, and I have a gorgeous blazer that this look lovely under.

BUT, I made a note that if I don’t wear it by the end of the year, I won’t keep it.

Maybe – Resell

On paper, this should have been a quick and easy toss during the first round edit.

I don’t like it, it’s not my style, and I haven’t worn it.

What is the problem?

It fits well, that’s the problem.

I have a hard time getting rid of something that fits my body well – even when I like nothing else about it.

I also think, what if, I wake up one day and suddenly need a blue and white polka dot blouse?

Or, what if I decide I love polka dots?

It’s just so silly.

But they are real thoughts too.

I pulled myself together, looked at my Pinterest board to remind myself of my style, and put it in my resell box.

No regrets.

Maybe – Donate

This Theory suit has tortured me for years.

It’s another example of an item that should have been a quick toss but I got in my head.

First, it doesn’t fit. It’s way too small for me.

Second, I haven’t worn it since before I had Vivi in 2019 (hence why it doesn’t fit).

But what if I loose a ton of weight and need a conservative black suit?

What then??

Also, this was one of my first splurgy wardrobe purchases.

And I loved it so much.

I felt so accomplished in it, I loved how I looked. I loved who I was when I was wearing it.

I think there is part of me that is waiting for that younger, slimmer version of me to come back, but she’s not and that’s ok.

Why it’s taken me almost four years to part with this is a mystery, but I donated it to someone who could benefit from it, and it feels good.

Continue this process until you have touched every item in your closet.

I don’t set a strict time limit here, but I did tell myself to get as much done in two hours as I could, and then I added an extra 30 minutes to finish up.

After: Dry Cleaning Ready to Go and Items to be Recycled

I pack up all the resell items and send them to Thred Up.

You can order a bag or do what I do and print a free shipping label and use a big Amazon Box.

You don’t make a ton of money with Thred Up.

In all the years I’ve been using them, I’ve received about $1500.

But it’s easy and low maintenance, and they donate or recycle whatever they don’t take.

Then action everything else, drop off your dry cleaning and tailoring, pack up the pieces to be recycled.

And take a break.

Tomorrow, in our final part, we break down how to set up and organize your closet, regardless of the size.

Related Posts

 Join Megan Kristel for a comprehensive, 3 hour long, LIVE Virtual Workshop sharing personal style and shopping tips for women over 40 on March 31, 2023.


Megan Kristel

Megan Kristel is an entrepreneur, working mom, and former personal stylist. Tired of the one-dimensional portrayal of women online, she founded The Well Dressed Life as a resource for other professional women.

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Tuesday 13th of June 2023

On Saturday morning, I spent two hours emptying my closet, dresser drawers and the storage boxes under my bed. Summer clothing for work, that I haven't worn since 2019 - mostly did not fit, so that was an easy donate! Pajamas that are well past their 'best before' date - good to go to recycling. I had everything out the door by Sunday morning, a small list of things that should be replaced, i.e. new white and black tanks. This all makes me sooooo happy! Winter accessories safely stored away. The only drawer left untouched is the dreaded underwear drawer....Thanks for the inspiration!


Tuesday 13th of June 2023

How do you feel about Poshmark for the effort that you put in and the reimbursement that you got back? Is it really worth it? And thanks for all the amazing content.


Tuesday 13th of June 2023

Where do I find how to tackle the "maybes". Post ends before there is any explanation or advice. Where do I go?