Before You Buy Anything, Answer This One Question

Elevate Your Style — Episode 1

If you're here from the video, hi. This is your homework, written out :)

And if you found this on your own — here's the short version. I spent thousands of dollars working with personal stylist, Samantha Dawn, and I'm walking through my entire process.

This is step one.

Where I was

I turned 30 and something shifted.

I felt more confident than I ever had. More like myself. And then I'd open my closet and none of it showed it. Everything in there belonged to a version of me I'd already left behind.

That's the gap. And I want to be really clear about something, because I wasted a lot of money learning it the hard way:

You cannot shop your way out of that gap.

Not because you're bad at shopping. Because you don't know what you're shopping for yet.

The trap

I felt sooo self conscious in this outfit but I felt like this was what I was “supposed” to wear to Fashion Week. I felt so uncomfortable and was trying to conform what I “thought” I should be.
I learned later that having all that volume in my shoulders was working against my inverted-triangle shape. The exaggerated top made my shoulders look even more broad.

Here's what I did instead, and what almost everyone does.

I found women whose style I loved — Hailey Bieber or Kathleen Post, mostly — and I tried to copy them. Bought the pieces. Saved the photos. Recreated the outfits.

It never worked. Not once.

Because I was copying the outfit without understanding my body, or my life, or what I actually wanted to feel. I was borrowing someone else's answer instead of finding my own.

An outfit works on someone because of everything underneath it. You can't skip to the top layer.

The first thing my stylist made me do

It had nothing to do with clothes.

No closet cleanout. No Pinterest board. No shopping list. Just one question, and she had me close my eyes and had me sit in it:

How do you want to feel when you walk into a room?

Not what you want to wear. How you want to feel.

That question felt almost silly to me at first. I hired someone to fix my closet and she's asking me about my feelings. But it's the whole foundation, and here's why:

Your closet is just the delivery system. It's how you get a feeling from the inside of you to the outside of you. If you don't know what feeling you're delivering, every morning is a guess. That's why you can have a full closet and nothing to wear — not a lack of clothes, a lack of direction.

Your homework

Three parts. They build on each other, so do them in order.

Part one: name the feeling

One question. One or two words.

How do you want to feel when you're dressed exactly right?

Some words to react to. You'll know pretty fast which ones are a yes and which ones are a no:

Powerful. Soft. Sharp. Effortless. Polished. Grounded. Expensive. Warm. Unbothered. Put-together. Quiet. Bold. Elegant. Cool. Feminine. Strong. Approachable. Untouchable. Creative. Clean.

Pick 2 -3 . The narrowing is the point.

Three ways to get unstuck

Think about the last time you felt genuinely great in an outfit. Not the most complimented — the most yourself. What were you wearing, and more importantly, how did you feel walking around in it?

Think about the opposite. Sometimes it's easier to name what you don't want. I knew I didn't want to feel fussy, or like I was trying too hard, long before I could name what I did want.

Ask ChatGPT. I'm not kidding. Tell it to talk to you like a personal stylist (even say a name if you have a fav stylist). Describe what you gravitate toward, describe what you own, describe how you want to come across — and ask it to help you name the feeling. It's genuinely good at putting words to something you can already sense.

What mine was

Confident and elevated.

A mix of feminine and masculine — I didn't have language for that at the time, that was just the feeling I kept circling.

It took a few weeks and a lot of conversations before I could say it that plainly. So if it doesn't come to you in an afternoon, that's completely normal. Sit with it.

Part two: your core style types

Now we turn that feeling into words you can actually use.

A style type is a category — a family of clothes that tends to create a certain effect. Most people are drawn to more than one, and that's not indecision, that's just how real style works. You're looking for three or four.

Some to react to:

Minimal. Classic. Chic. Sophisticated. Edgy. Romantic. Boho. Preppy. Street. Maximalist. Sporty. Western. Utilitarian. Feminine. Tailored. Relaxed.

Three questions that get you there faster than staring at the list (again throw this into Chat):

What's your go-to feel-good outfit? The one you reach for when you want to feel like yourself. Describe it out loud. The words you use are usually your style types hiding in plain sight.

Who's your style icon? And be honest — not the most impressive answer, the truest one.

What silhouettes or shapes do you keep coming back to? Look at what you actually own and wear, not what you own and avoid.

Then pick three or four words. Not one — one is too narrow and you'll feel boxed in. Not eight — eight is the same as none.

Mine are: minimal, chic, sophisticated, subtle edge.

One thing worth noticing about my four: three of them are quiet and one isn't. That's on purpose. The edge is the thing that keeps the other three from being boring. When you pick yours, look for the one word that's a little different from the rest — that's usually the most you part.

Part three: your style personality

This is the one you'll use forever, so don't skip it.

Take your three or four words and turn them into a single sentence describing a woman. Not a list — a person.

Mine is: the sophisticated and edgy chic woman who fearlessly stands out.

This works because the **deep V-neck draws the eye inward, the defined waist creates shape, and the looser shorts add balance through my lower half.** Instead of emphasizing my shoulders, the silhouette makes my proportions feel more balanced. Scroll back up for comparsion 😂

When I'm shopping now, I don't ask do I like this? Liking something is easy and it's why my closet used to be full of clothes I never wore. I ask one question:

Does she wear this?

If the answer is no, it goes back on the rack. Doesn't matter that it's cute, doesn't matter that it's on sale. It's not hers.

That one question has saved me an absurd amount of money, and it's the reason my closet finally works — everything in it belongs to the same woman.

So write your sentence. Say it out loud. It should feel a little bold, like you're describing someone slightly ahead of where you are right now. That's correct. You're naming who you're dressing as, not who you've been.

Keep it somewhere you'll see it. You'll be using it every time you shop from here on out.

What happens next

Next episode we go deeper on finding your style types — including the mistake I made that cost me the most money, which is the difference between a style you admire and a style you actually align with. If you've ever bought something you were obsessed with and then never worn it, that's what we're fixing.

But everything from here is built on these three answers. Your feeling. Your words. Your sentence.

So take the week and do the work!

Then come tell me — drop your style personality in the comments on episode one. I read all of them, and I want to see who you're becoming.

#womenover30style

Finding Your Style - Part 1