We had the good fortune of connecting with Rugila Jones and we’ve shared our conversation below.

Hi Rugila, what was your thought process behind starting your own business?
Honestly, it started from doing it for years without calling it a business. I’ve always been the person helping friends style outfits, build wardrobes, or find pieces that just worked for them.

Over time, I realized not everyone wants to overthink fashion; they just want to feel confident and look good without the stress. That’s what pushed me to create Careless Wins and Styled By Ru – something that brings that effortless, “cool without trying too hard” feeling to more women.

What should our readers know about your business?
My business is built around one core idea: making style feel effortless, elevated, and accessible. Through Careless Wins, my online boutique, and Styled By Ru, my personal styling services, I help women feel confident without overthinking what they wear. It’s all about that “put-together without trying too hard” energy.

What really sets me apart is that I don’t just sell clothes I curate a point of view. Every piece I select and every look I style is intentional, wearable, and designed to fit into real life. With over 15 years in the fashion industry and a background in Fashion Merchandising & Design, I’ve developed a strong eye for what works, what lasts, and what actually makes someone feel good in their own skin.

Getting to where I am today definitely wasn’t easy. Like most entrepreneurs, I started by doing everything myself, sourcing, marketing, styling, building the website, showing up at markets while figuring things out in real time. There were moments of doubt, trial and error, and learning how to stay consistent even when things felt slow. But I leaned into resilience, trusted my instincts, and kept showing up. Over time, that consistency started to build momentum.

One of the biggest lessons I’ve learned is that you don’t need everything to be perfect to start, you just need to start. Growth comes from action, not waiting. I’ve also learned the importance of community and connection. Every customer, every client, every conversation has played a role in shaping my business.

What I want people to know about my brand is that it’s more than just fashion, it’s about confidence. I want women to feel like the best version of themselves in what they wear, whether they’re running errands, going on vacation, or showing up for a big moment in their lives. If I can make getting dressed feel easier and more empowering, then I’ve done my job.

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
If my best friend was visiting San Diego, I’d plan a week that mixes beach, food, and a little bit of glam. We’d start in La Jolla for ocean views and sunsets, do a beach day in Pacific Beach, and spend time in Little Italy (my favorite) for coffee, markets, and great Italian food.

We’d add a fun night out downtown, a chic day in Coronado at the beach and Hotel del, and a drive up to Encinitas for that laid-back coastal vibe. I’d also squeeze in a wellness day, Pilates, brunch, and a little reset.

What I love most about San Diego is how it effortlessly blends relaxed beach energy with an elevated lifestyle. Every day feels easy yet special.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
I’d definitely dedicate this shoutout to my family and close friends, who have been incredibly supportive throughout my journey. Starting a business comes with a lot of uncertainty, and having people who believe in you, even on the days you’re figuring it out as you go – makes all the difference.

I also give a lot of credit to the communities I’ve been part of, both in fashion and entrepreneurship. Being surrounded by creative, driven individuals has pushed me to grow, take risks, and stay inspired. And honestly, every client and customer who has trusted me with their style or supported my business has played a huge role in getting me to where I am today.

Website: https://carelesswins.com

Instagram: @carelesswins

Nominate Someone: ShoutoutSoCal is built on recommendations and shoutouts from the community; it’s how we uncover hidden gems, so if you or someone you know deserves recognition please let us know here.