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Signs It’s Time To Start Working With A Stylist

  • Writer: Jamie Lewis
    Jamie Lewis
  • Oct 9
  • 3 min read

Here’s the thing: your clothes are talking before you even open your mouth. And if for a while now you’re looking in the mirror and thinking to yourself- “this is it?!” especially after you just spent 20 minutes trying to pieces something together- that’s your sign—it might be time to bring in a personal stylist. It sounds like ALOT—but you knew when it was time to outsource other areas when that started feeling overwhelming:


The cleaning service—best investment you’ve ever made


The personal trainer—you’re finally not lost at the gym


The hairstylist—that actually does your hair 10/10- best upgrade


You get where I’m going….


So when do you really know you’re ready for styling help? Let’s break it down. There’s a few key indicators that this is past a DIY run to Nordstrom’s buy a few new pairs of jeans situation..


Signs it's time to start working with a stylist

1. You’re in a life transition.

New job, becoming a mom, stepping into leadership, or even just entering a new season of life—your wardrobe has to evolve with you. If your clothes don’t match the role you’re stepping into, you’ll feel it every morning. I always look at it this way- there might be something cohesive with my style with the way I dressed when I was 21—but my life from then is so vastly different. I’m not her anymore- and have lived so many lives since then-so it would be odd if I still held on to the exact same pieces- we evolve our style as our life evolves. 


2. Shopping feels overwhelming.

If you walk into a store (or scroll online) and your brain short-circuits, that’s not a lack of style—it’s decision fatigue. There’s too many choices- too many departments-it’s sensory overload and it’s not within your wheelhouse to pick the pieces that are truly giving you the style you want. You grab or add to cart way too soon because you don’t want to deal-BUT the pieces you’re picking are not it. 

My job is simply—to curate for you, so instead of “Where do I even start?” it becomes “Wow, this feels like me.”


3. You keep buying, but nothing works together. 

If your closet is packed yet outfits never come together, that’s a strategy problem, not a “you” problem. There’s no plan—so your pieces actually mix, match, and elevate.You didn't purchase thinking about the cost-per-wear, how many different outfits it can go back to- what gap that piece is filling in your wardrobe. You simply just purchased—and now, nothing is complete. It’s like a puzzle everything hanging should have a purpose to mix it together. 


4. You’re craving confidence. 

Clothing has energy. The right outfit can shift how you walk into a room, how you show up in photos, even how you feel on a random Tuesday. If you’ve been hiding in “safe” clothes and want to finally feel like your best self, styling will get you there. A strong outfit really is the only way you can represent outwardly how you want to represent yourself. A look that’s head turning will get you the compliments and those compliments are going to give you that surge of confidence you haven't felt before.


5. You’re ready to invest in you

A personal stylist isn’t about chasing trends—it’s about alignment. Style is self-expression, and when you’re ready to show up authentically and powerfully, the right wardrobe is the most visible first step.


The bottom line: if you’ve been circling your closet, frustrated that it doesn’t reflect who you are or where you’re going, it’s time. A stylist is not just about clothes—it’s about unlocking the version of you that’s already there.


Now let’s be real—does one of these sound like you right now? Because if it does, your timing is perfect. ✨


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