Why Cleaning Out Your Closet Feels So Hard (& What Actually Works)
A stylist’s guide to doing it without the tears, shame spiral, or 8-hour mess.
Let’s be honest, cleaning out your closet sounds productive in theory… but in practice?
It’s overwhelming.
It’s emotional.
It’s that thing on your to-do list that keeps getting bumped to “next weekend.”
Even for the most stylish, organized women I work with, closet cleanouts bring up a lot. Guilt over money spent. Frustration about clothes that no longer fit. Sentimentality. Decision fatigue. It’s all totally normal!!
But it doesn’t have to stop you. And it doesn’t have to be all or nothing.
Why It Feels So Hard
Let’s break down a few real reasons closet cleanouts feel like a mental minefield:
1. You’re emotionally attached to your clothes.
That dress you wore on a special trip. The blazer from your first big job. The jeans that used to fit and you hope might fit again. These pieces hold stories. Letting go can feel like letting go of part of you.
2. You’re stuck in the “what ifs.”
“What if it comes back in style?”
“What if I lose weight?”
“What if I suddenly get invited to a white-tie gala??”
Those what ifs keep us holding on, even if the item doesn’t actually serve us anymore.
3. You’re afraid of regretting a decision.
Maybe you’ve donated something in the past and then missed it. Or you’re scared you’ll toss something and need it next month. That fear of regret can paralyze the whole process.
4. You’re trying to do it all at once.
Cue the mountain of clothes on the bed and the 3 p.m. meltdown. Cleaning out your entire wardrobe in one go sounds satisfying, but it’s often just… exhausting.
What Actually Works
From a Stylist Who’s Done Thousands of Closet Cleanses
Whether you're doing it solo or with support, here’s what helps:
1. Break it down by category.
Start with shirts. Then pants. Then shoes. Don’t try to tackle the whole closet at once, it’s too much. Focusing on one section makes the process more manageable and way less stressful.
2. Use a simple sorting system.
You need more than just “keep” and “toss.” A good sorting method helps you make smart, confident decisions based on why something is staying or going.
Ask yourself:
Would I wear this tomorrow?
Does this still fit my body and my life?
If I saw this in a store today, would I buy it again?
👋 Inside The Wardrobe Reset, I share the exact sorting system I use with clients — the same one that makes closet cleanouts easier, faster, and way less stressful.
3. Try it on. No exceptions.
Even if something used to fit, or technically still does, TRY IT ON. Our bodies, lifestyles, and preferences change. What used to be a go-to might now feel off. That’s not failure. That’s growth.
Stylist tip: When trying on tops, wear them with your go-to pants. When trying on jeans, pair them with a tee you love. That way, you’re seeing each piece in its best light.
4. Take photos. Seriously.
The mirror lies. Your brain lies. Your memory lies.
A selfie gives you a more objective view and helps you see if something’s truly working.
Want a Printable Step-by-Step Closet Cleanse Guide?
I have a free resource that walks you through the exact process I use with clients, including a 10-step checklist and flowchart to help you decide what stays and what goes.
And if you’re ready for even more support, including videos, demos, real-life try-ons, and stylist-approved strategy, check out The Wardrobe Reset, my self-paced masterclass designed to make your closet feel like a place you actually want to walk into.
Cleaning out your closet isn’t about perfection. It’s about clarity. It’s about making space — for ease, for confidence, for the version of you who doesn’t dread getting dressed. And if you want support through the process?
The Wardrobe Reset is here for you.
It’s a self-paced video masterclass that walks you through a real-life, stylist-approved closet cleanse with me, Hallie, guiding you every step of the way.
You’ll learn how to:
✔ Let go without guilt
✔ Decide what stays and what goes
✔ Organize your wardrobe in a way that actually works
✔ Reconnect with your personal style
The Wardrobe Reset is available anytime. It’s $79. And it’s here to make this process feel a whole lot lighter.
The Wardrobe Reset | Closet Cleanse Masterclass
This masterclass is your step-by-step, stylist-approved guide to editing your closet with confidence and without the drama. Whether you’re dealing with a packed wardrobe, decision fatigue, or a pile of “what was I thinking?” pieces…I’ve got you!
✔ 6 self-paced video modules
✔ Step-by-step closet cleanse system
✔ Printable worksheets + clothing tracker
✔ Unlimited lifetime access
✔ Bonus: TWC Shopping Guide ($49 value)