If you’ve ever stood in front of your closet thinking, “I don’t know why certain things work for me, and others don’t,” you’re not alone. The good news? There’s a simple way to figure this out—and it starts with the clothes you already love to wear.
Believe it or not, you need data. The more informed you are about yourself and your style, the easier styling and shopping will become.
Step 1: Identify Your Favorite Pieces
Go to your closet and pull out the items you reach for over and over again—the ones that make you feel good every time you put them on. These are your Daily Dependables—pieces that never fail you.
Now, get super clear on why they work for you:
✔️ Color: Do you gravitate toward certain shades?
✔️ Fabric: Do you prefer structured pieces or soft, flowy materials?
✔️ Fit & Silhouette: What shape is it? (A-line skirt, mid-rise jeans, pencil-leg trousers, etc.)
Once you’ve identified these key details, compare one of your favorite pieces to something similar in your closet that you don’t love as much. You’ll quickly see the difference:
- Too big in the bust?
- Sleeves too tight?
- Wrong length for your proportions?
A lot of us buy items that we think are similar assuming they will work for us just as well. For example, a client I worked with recently loves long floral dresses. The fit of each dress looked similar, but in reality was very different. It frustrated her to no end, “Why do some of the dresses work and make me feel good while others don’t?”
When we identified that she had a petite frame, the mystery was solved.
What is your most-worn and loved category of clothing? Are you a dress gal? Jeans, skirts, or pants gal?
When you identify what your core, go-to items are, you are better equipped to understand your style.
Step 2: Replicate What Works (Without Buying the Same Thing Over and Over)
The goal isn’t just to buy duplicates of what you love—it’s to use what you know works and expand your wardrobe strategically.
For example, if you love an A-line mini skirt, try experimenting with:
- A longer A-line skirt in a different style (great for spring & summer).
- An A-line midi skirt in a structured fabric for a polished, elevated look.
- A corduroy, suede, or leather version for fall and winter.
This way, you’re giving yourself styling options while sticking to the fit and feel that makes you feel most confident.
Step 3: The Most Important Part of Your Wardrobe—Your “Most Worn” Section
Let’s talk about what I believe is the most important part of your wardrobe: your most worn section.
We all have that handful of items we wear constantly—not necessarily because we love them, but because they just… work. I want to focus on the items you reach for because they genuinely make you feel great.
For many of my clients (and myself included), this tends to be bottoms—jeans, trousers, casual pants, etc. Why? Because once you have a few pairs of bottoms that fit perfectly, styling the rest of your wardrobe becomes infinitely easier.
Step 4: Build a Foundation of Reliable Bottoms
According to online data, the largest section of most women’s closets are tops—tees, blouses, sweaters, and cardigans. But in my experience shopping for bottoms is the most challenging item to shop for. Without your dream fit of bottoms, all of your top options remain under-utilized.
When you have 5-6 pairs of bottoms that fit like a dream, you suddenly unlock endless outfit possibilities.
Think about it:
✔️ A few great pairs of jeans (mid-rise, wide-leg, straight-leg, etc.)
✔️ Tailored trousers for a polished look
✔️ Casual options like fatigues, chinos, or relaxed pants
If your bottoms fit well and make you feel amazing, getting dressed in the morning becomes effortless.
99% of my clients have had success shopping for jeans and some pants at Madewell. You need to find a brand that caters to all women. Look online for brands that offer:
- Petite
- Petite Plus
- Curvy
- Tall
- Regular
You want to be able to mix and match your fits so that you can find that dream pair of jeans for you. You might need to try a different rise and inseam to find the fit that finally works best for you. It’s out there! Trust me.
Step 5: Use Your Closet to Understand Your Body Shape
A lot of women come to me saying, “Bri, I don’t know why some things work in my closet and others don’t.”
Here’s the secret: you already have the answers hiding in your wardrobe.
Yes, body shape analysis can be helpful, but if you look at the pieces you already love and wear most often, you’ll start seeing a pattern. That’s your body’s way of telling you what works.
Step 6: Stop Buying the Same Thing in Every Color (and Instead, Expand Your Wardrobe Thoughtfully)
Have you ever bought 5 tops in different colors, only to realize you don’t actually wear them? 🙋♀️
The key to not getting stuck in a style rut is understanding why you love a specific piece and then translating those qualities into a different garment.
Example:
One of my clients loved mini skirts—they made her feel confident and stylish. But instead of just buying more mini skirts, we identified what about them worked for her:
✔️ A fitted waist
✔️ A little bit of flare around the hips
✔️ A structured but comfortable fit
With this in mind, she could expand her wardrobe by trying:
- A fitted pencil knee-length skirt in a form-fitting fabric
- A midi skirt with a fitted waist but different fabric or style
By understanding what makes you feel your best, you can confidently build a wardrobe that works for you—without overbuying or feeling stuck in a fashion rut.
Final Step: Put This Into Action Today
Tonight, I want you to try this:
1️⃣ Pull out your favorite, most-worn piece.
2️⃣ Compare it to a similar item you don’t wear as often.
3️⃣ Ask yourself: What’s different? Is it the fit? The fabric? The color?
4️⃣ Use these insights the next time you shop.
Getting dressed may never feel 100% effortless—and I don’t think it should. We will always need to put in effort. But when you start dressing in a way that aligns with your personal fit and style, the effort you’re putting in will feel rewarding.
I encourage you to dig in and apply these tips to your most worn pieces. I’d love to hear what pieces work best for you and what you discover.
🌿Hey! Heads up. Ready for a Spring Wardrobe Refresh? 🌿
Now that you know why some clothes work for you and others don’t imagine how much easier (and more exciting!) getting dressed could be with a spring wardrobe that truly fits your style, body, and life.
This season is the perfect time to edit, refresh, and refine your closet so you can step into spring feeling more confident and stylish without wasting more time and money.
✨ Want a pro to help you get there faster? ✨
Please stop trying to do this alone. You need expert support to collapse your timeline and get you the results you’ve been daydreaming about.
I’m currently booking Spring Styling Sessions, where I’ll help you:
✔️ Identify what truly works for you (so you stop second-guessing your outfits).
✔️ Curate a wardrobe that’s perfect for your shape, lifestyle, and goals.
✔️ Fill in any gaps with intentional spring shopping picks (no more wasted purchases!).
If you’re ready to take the guesswork out of getting dressed this season, let’s do this together!
Click here to book your complimentary 15-minute Style Clarity session.
Leave a Reply