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The Untapped Power of Personal Style for Female Attorneys

Choosing what to wear can be mental gymnastics for us as women. 


We hold up one outfit at a time, saying, “Does this work? Nope. Does THIS work? Nope.” 


Pretty soon, we’ve gone through ten decisions before 7:00 AM, and we haven’t even landed on an outfit. 


No wonder we have decision fatigue at the end of the day. 


Estelle Winsett gets it. She remembers being a young lawyer, going with the career service advice which was: wear boxy suits in black and gray so you blend in. 


As a new associate learning the ropes, this advice worked fine for her, but Estelle believes that as you evolve, your style should evolve with you. 


After spending over fifteen years working in or close to the legal field, she eventually created a professional development department at a Big Law firm. Marketing and branding was a significant part of her role there, which piqued her interest in how style could be used as a tool to brand yourself. 


She dove into this idea, eventually becoming a personal stylist through Cabi, a home-based fashion brand that provides personal styling for women. After 6 years working with Cabi, she felt a pull to expand and branch out to other brands. So she went down the road of getting her professional and personal style certifications. 


(We’re lawyers, so we gotta go through all the courses and get all the certificates, right?)


From the beginning, Estelle loved seeing the transformational nature of style as her clients started to feel more powerful and confident, simply from finding the right clothes. 


The voice inside of her kept saying, “I should do this more.”


So in August of 2023, she went into full-time business as a personal and professional stylist. 


Estelle knows firsthand what it’s like to be a female in the law, so I was eager to sit down with her and hear her best tips and style secrets for female attorneys. 


Here’s what she shared: 


Create your unique signature style. 

Before she ever does any shopping, Estelle helps women create their own signature style.


A great tool for this is Pinterest. Create your own Pinterest board, and start pinning your style inspiration. As you pin a lot of different images, themes will start to arise. Even if you don’t think you have a style, you’ll start to see patterns. After you pin eight pencil skirts on your board, you’ll say, “Huh, it seems like I kind of like pencil skirts.” 


You can also use TV characters as inspiration. A lot of people like Alicia from The Good Wife or Olivia Pope from Scandal. Find a style you like, figure out what your themes are, and start to create it for yourself. 


From there, see what you already have in your closet that fits your new style. If there are items you don’t have, you can start to look for them when you’re shopping. 


Don’t get caught up in feeling like you have to change everything at once!! Take baby steps. 


Let Your Style Evolve Over Time

Your style likes and dislikes evolve over time. You might put on something you used to love and then all of a sudden, it’s just not you anymore. That’s okay and natural. That outfit or piece of clothing served its purpose, and now it’s time for something you feel really good in now


This is especially true as you get into leadership roles. If you make partner at your firm, you don’t want to dress like you did when you were an associate. You want to embody your new role, and style is a great tool to do that. 


Do a closet cleanse. 

Estelle recommends cleaning out your closet at least twice a year. The goal is to get rid of everything that’s not working. Get rid of those items that don’t fit your body, that you no longer feel good in, and don’t fit your new style. 


As women, this is one of the biggest challenges for us. But when you’re trying to get dressed in the morning and you pick up five different garments that are too small, it’s depressing. No one wants to start their day like that. Get those out of there, and replace them with clothes you feel good about. 


If you’re on a diet and you know your clothes will fit soon, great. Put them in a box, and store them under the bed. You can always pull them out later, but the last thing you need in the morning is to have a bunch of clothes mocking you because they don’t fit. 


This is going to help you reduce decision fatigue and actually be able to use your mind for work, without clothes taking up all your mental energy. 


Embrace Your Femininity

When we embrace our femininity with our style, that’s when we start feeling authentic. If you're trying to dress in a way that doesn't bring out who you truly are, that's when you don't feel good in your style. Femininity and power are not mutually exclusive. In fact, it's really a superpower when a woman dresses in a way that lights her heart up, because then she's able to go out and do great things in the world. 


I walked away from this conversation INSPIRED and ready to clean out my closet and get rid of all the stuff that’s not working.


We’re so blessed to have Estelle as a resource. Go out and follow her for all of the fashion tips:


Instagram: @estellewinsett




You deserve to feel good about yourself RIGHT NOW. 


Not after you lose a few pounds, or after you go back to the gym, but right now. 


You deserve to walk into Starbucks and hear things like, “Oh my gosh, I love your earrings.” 


Then walk to your car feeling like a badass. 


Because that’s who you are, my powerhouse friend. 


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