Closet Clean-Out Challenge

Week 2: Jeans, Shorts, Pants & Skirts – Building the Bottom Half That Works

Hey Bestie,

We kicked things off last week with a mindset reset: prepping our closets (and our hearts) for what’s ahead. Now it’s time to dive into the pieces that literally hold everything together: your jeans, shorts, pants, and skirts.

I know I originally said we’d tackle bottoms in Week 3, but as I started cleaning out my own closet, I realized, we have to start with the foundation. The BOTTOMS! When your bottoms don’t fit well or make you feel uncomfortable, it doesn’t matter how cute your top is.

These pieces are the foundation of most outfits, and starting here is actually helpful, especially when we get to the tops section next week. That way, you’ll be trying on tops with the pants you actually like to wear and can better tell what works together.

Honestly, this is one of the hardest categories for me personally. If you’re anything like me, you probably have a few pairs that make you feel just “meh,” or things that just don’t fit your body as it is today. It’s time to change that.

This week, we’re going all in. You’re going to figure out what fits, what you love, and what’s just taking up space. The goal? A closet full of pieces that make getting dressed feel good - from the bottom up.

Pro tip:

Grab a notepad or open the notes app on your phone and jot down your thoughts as you clean. Trust me, it’s worth the time.

• Maybe you have way too many black pants. You do not need to buy another pair of black pants.

• Notate if there’s a specific pair of bottoms you love. Get detailed! Where are they from? Do they have stretch? What’s the fabric like?

You’ll thank yourself later. Not only can this help you avoid buying duplicates, but it also helps you shop more intentionally: looking for fits, fabrics, and styles that actually make you feel amazing.

I’m doing this right along with you, bestie. You’re not alone. Below is a screenshot of how I’m organizing my notes in my phone! (Feel free to copy it!)

Closet Friend Groups: Bottoms Edition

The Besties: Your go-to jeans, shorts, pants, and skirts. They fit just right, go with everything, and make you feel confident every time you wear them. No hesitation, these are your ride or dies.

The Friend List: Not everyday players, but they serve a purpose. Maybe it’s that pair of work trousers or a statement skirt for date night. If you actually wear it and it works with your besties, it can stay.

The Ex’s: Let’s not hang on to pieces just because they used to fit or we wish they worked. If something rides up, sags weird, digs in, or just doesn’t feel good—it’s time to let it go. Life is too short for uncomfortable pants.

This Week’s Challenge: The Bottoms Edit

1️⃣ Take them all out: jeans, trousers, joggers, skirts, shorts, everything. Yes, even the ones hiding in the back of the drawer. Pile them on your bed!

2️⃣ Sort into friend groups: be honest with yourself. If you haven’t worn it in a year or it doesn’t make you feel good, it’s probably not a bestie.

3️⃣ Try them on: I know it’s a pain, but it matters. You might be surprised by what still fits and what definitely doesn’t.

4️⃣ Let go of the ex’s: donate or sell the pieces that aren’t serving you anymore. Make room for styles that actually support your current life and body. You deserve it!

If you get stuck, it’s totally okay.

Make a pile we’ll call your “suss friends” for now. Sometimes, you’re just not in the right headspace to make a decision, and that’s normal. We might not be able to get a read on certain pieces today, and that’s why I’m inviting you to join me in the 30 Days of Everyday Outfits Challenge on IG.

I’ll be styling my “suss friend” pieces and seeing if they truly belong in my wardrobe.

• If I can’t figure out how to style them, or if I don’t feel like myself after trying, it’s a no.

• But if I can style it in at least three ways and it makes me feel good? We’re promoting it to the “friend list.”

This isn’t just about cleaning out, it’s about learning. Let’s gather more info and trust the process.

Questions & Prompts to Ask Yourself While Cleaning Out:

• Do I actually wear this? When was the last time? How do I feel when I wear it?

• Is it a special occasion piece or just something I think I might wear someday? Can I name 2–3 ways or places I’d actually wear it? If not… it’s time to say goodbye.

• Does anything about it bug me: color, fabric, size, fit?

• If it doesn’t fit, am I really going to pay to get it tailored or fix that missing button this week?

• Does this piece work with my “closet besties”?

• Does it complement my wardrobe—or does it clash?

⚠️ WARNING: Do Not Get Distracted!

Scenario: You’re on a roll, clearing out bottoms left and right, and you think, “Let me just keep going and do tops too!”

Bestie, I know because I do this too.

But this is a marathon, not a sprint. Decision fatigue is real, and pushing too far will only leave you drained. When you finish with jeans and pants, check it off your list and treat yourself to some “me time.”

Focusing on one category at a time helps us make intentional choices, reflect clearly, and really figure out what we love vs. what we just keep around.

This is deeper than decluttering, it’s about getting to know yourself again. So take your time, make some notes, and start to see a clear picture of who’s in your closet “friend group.” No toxic friends allowed, they’ll just drag us down later.

When you’re done, you’ll be left with a selection of bottoms that actually work for your life, and your tops, when we get to those next week.

You’ve got this. Every drawer you clear, every hanger you free up, brings you closer to a closet that truly feels like you.

See you next week for Tops & Sweaters (finally!), and I’ll check in midweek because, let’s be honest, I’ll probably need the motivation too.

This work is hard, but it’s so worth it.

Love you, bestie.

- T 💛