The One Question That Will Change How You Get Dressed
Stop second-guessing your outfits. Start dressing for the woman you’re becoming.
It’s not “Does this feel like me?”
It’s not “Does this check my 3 words?”
Those questions have their place. But they don’t move the needle the way this one does:
“Would Future Me thank me for wearing this?”
Here’s why it matters. Many of my clients come to me because they can’t fully articulate how they want their style to change — but they do know the way they’re dressing right now doesn’t feel aligned with the woman they’ve become.
They’re accomplished, intelligent, and capable. And yet, getting dressed can still feel like a mental obstacle course — trying on multiple outfits, second-guessing every choice, and settling for something that’s merely “fine.”
The truth is, your style should evolve in step with your life. As your career grows, as your priorities shift, as you refine what matters most — your wardrobe must keep pace. This is not about vanity; it’s about alignment. The same way you prepare for the role you want, you should dress for the woman you are becoming.
That’s where the question comes in: Would Future Me thank me for wearing this?
It’s not a trick. It’s a filter — one that quickly separates the clothes that hold you back from the ones that move you forward. Ask yourself:
Does this outfit reflect where I’m headed?
Does it support the opportunities I’m pursuing?
Does it present me as the woman I intend to be?
Consider these moments:
School drop-off to client meeting: Future You — the one commanding the boardroom at 10 a.m. — will thank you for choosing tailored trousers over the leggings you’ve outgrown even for those Zoom calls.
Last-minute networking invite: Future You — the one making a lasting impression — will thank you for already being in a sharp blazer instead of scrambling for a quick change.
Morning Zoom presentation: Future You — the one owning her expertise — will thank you for wearing a statement blouse that frames your presence as much as your words.
Outfit formulas and styling frameworks are tools, guardrails to keep you on track, but they are not the goal. The goal is a wardrobe that works as hard as you do, one that makes your daily decisions faster, simpler, and undeniably yours.
When you start dressing with Future You in mind, hesitation disappears. You step into your day assured. And your style becomes not just effortless, but inevitable.
Here’s to your Future You!
xx,
Want to start building a wardrobe to meet your “Future You?” Apply to work with me here.