Closet Clean-Out Challenge

Week 4: Dresses – Reclaiming the One-and-Done Piece

Hey bestie,

We’ve made it to Week 4! You doing okay? Any closet meltdowns? I only had one (proud of me). This week is all about a category that’s supposed to make life easier… but let’s be honest, it doesn’t always. Enter: dresses.

Dresses are the ultimate “throw it on and go” item, but if you’ve ever stood in front of your closet staring at a rack full of dresses and still felt like you had nothing to wear, you’re not alone.

This week, we’re asking:

Do your dresses actually work for your life right now?

Do they make you feel confident? Comfortable? Like yourself?

Are they besties… or just pretty strangers taking up space?

Because whether it’s a wedding guest dress you swore you’d wear again, or a flowy linen number that somehow only works on vacation, it’s time to figure out what stays and what no longer serves you.

Closet Friend Groups: Dresses Edition

The Besties

They’re your go-to’s. You feel good in them. They require zero effort and always get compliments. They work with your lifestyle and your favorite shoes. These deserve prime real estate in your closet.

The Friend List

You might not reach for them every week, but they have their moment. Maybe they’re seasonal staples, special occasion backups, or sentimental pieces you actually wear. As long as they serve a purpose, and don’t cause chaos when you’re trying to get dressed, they can stay.

The Ex’s

They’re beautiful… but they don’t fit right. Or they never leave the hanger. Or you’re constantly tugging, adjusting, or avoiding them altogether. Maybe you’ve outgrown the vibe or the phase they belong to. If you wouldn’t pack it for a weekend away or wear it out to dinner right now, it’s probably time to say goodbye.

This Week’s Challenge: The Dress Edit

1️⃣ Pull out every dress you own. Casual, formal, lounge-y, seasonal… all of them.

2️⃣ Try them on (yes, really)! This will be the most telling part of the process.

3️⃣ Sort them into friend groups.

Ask yourself:

Does this make me feel like me?

Do I know when and where I’d wear this? I like to have 2-3 occasions in mind to keep.

Would I choose this over my go-to pants + top combo?

If I was out shopping today, would I repurchase this item?

4️⃣ Let go of the ex’s. Donate, sell, or pass along to a friend who might love it more. Holding onto clothes that don’t fit your life anymore just creates clutter - physically and mentally.

I’m right there with you this week! Going through dresses that have lived in garment bags since 2021 and asking myself if they’re still part of my story.

Remember: you’re not curating a fantasy life closet, you’re building a wardrobe for the version of you that exists right now.

And next week? We’re wrapping up with coats, jackets, and the final touches that pull everything together. But for now, let’s give the dress rack the love (and edits) it deserves.

Let me know how it’s going, what surprised you, and if any “ex’s” gave you a hard time. I’m always a DM away. 💛

You’ve got this.

—T