We recently connected with Ashley Ayres and have shared our conversation below.

Hi Ashley , thanks for joining us today. Alright, so you had your idea and then what happened? Can you walk us through the story of how you went from just an idea to executing on the idea

I think what’s interesting about my business is that it didn’t start with a single “aha” moment. It was built over time, long before it officially had a name. I had a strong sense of entrepreneurship laid out for me. My father was a serial entrepreneur, my maternal grandfather had his own produce business and my paternal grandparents owned a shoe store for a time. I was the girl who was the first one to hit the pavement when our elementary school would launch a fundraiser to sell wrapping paper or gift products.

I’ve worked in the apparel industry for over 20 years, from custom product to working one-on-one with women through boutique-style jewelry and accessories trunk shows. So for a long time, I was already doing the work helping women figure out what worked for their bodies, their lifestyles, and their confidence. I just hadn’t packaged it as my own business just yet.

At the same time, I was raising four kids (11, 9, 3 and 1) in 2020, managing a household, and navigating a full, very real life. So the idea of creating my own personal styling business was something I wanted to do but I wasn’t sure just how. I was in the thick of motherhood and leaning on wine nights a little too heavily after my youngest son was born. There were many long days and nights as we navigated the challenges that come along with a special needs diagnosis. Lot’s of doctors appointments and therapy. I sought my own therapy and was prescribed an anti-depressant to help me get through. By the end of 2020 I was feeling horrible. Turned 40, hadn’t really lost the baby weight and was drinking too much in conjunction with my prescription. I felt horrible and decided in November of 2020 I need to get my head clear. I first was weened off my medication, then decided that I need to have a serious look at my drinking. On December 14, I took my last sip of alcohol. This is when things really shifted. It was what was needed in order to make the idea of launching a styling business possible.

I let a “lack of degree” hold me back for far too long. To supplement that I hired business coaches and leaned on a local networking group of women as well as took a few online styling courses to help me get started. Having a strong network of women and coaches has been essential to my growth.

In the beginning, it was very scrappy. I reached out to women in my network, my sisters, my friends and started offering styling sessions only virtually, and paid close attention to what they actually needed not what I thought the business should look like. I started noticing the same conversation coming up with my friends where we felt discouraged trying to dress bodies that had changed, but without a clear roadmap for what worked now. I didn’t have everything figured out, but I knew I could help.

From there, it was a lot of learning in real time. I had to figure out how to structure my services, how to price them, how to communicate my value, and how to show up online in a way that felt authentic. Most of my client materials were a mix of google docs and canva slides. Eventually getting out of my immediate friends and family group and having tremendous local success with referrals was huge!

It wasn’t overnight. It was one client, then another. One conversation, then another. And with each step, I got clearer on what I was actually building. Over time, that evolved into Collectively Styled the personal styling business that isn’t just about clothes, but about helping women reconnect with themselves in a really tangible through style.

Ashley , love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?

What really pushed me to build something of my own was a combination of life experience and personal transformation. I’m a mom of four, and like so many women, I went through seasons where I felt disconnected from myself. After turning 40, I noticed the same conversations coming up with my friends. We were frustrated trying to dress bodies that had changed, without a clear understanding of what actually worked anymore.

Around the same time, I got sober, and that gave me a level of clarity and courage to finally move forward with building a business that felt aligned with who I was becoming. I didn’t want to just help women “get dressed” I wanted to help them reconnect with themselves through their own transformations.

What I offer now is a range of styling services, from high-touch style transformation programs to closet edits, virtual styling, and brand or event styling. A big part of my work is helping women rework what they already have, shop more intentionally, and build a wardrobe that actually supports their real life.

I think what sets me apart is the way I approach styling. It’s not intimidating, and it’s definitely not reserved for celebrities. I bring a lot of warmth and intuition into my work, which helps my clients feel comfortable, seen, and supported especially if they’re feeling unsure or overwhelmed. I meet women where they are and help them take baby steps throughout the process.

I also really believe that great style doesn’t require an endless budget. I grew up very much on TJ Maxx (before it was cool) and hand me downs. I have a great eye and find some of my most cherished clothing from thrift stores. I love showing women how to mix high and low pieces, invest in what matters, and let go of the idea that more is better. For me, it’s about building a smart, strategic wardrobe that makes getting dressed easier, not harder.

I’m most proud of the relationships I’ve built with my clients and the trust they place in me. This work is personal. It’s not just about clothes, it’s about confidence, identity, and how women show up in their lives. I once watched and celebrated a client over zoom who accepted a job offer on the spot while we were on our styling call together. We had styled her just about two weeks before that for her job interview in NY.

What I want people to know is that you don’t have to have it all figured out to start feeling better in your style. You don’t need a complete overhaul or a perfect body. You just need the right support, a thoughtful approach, and a willingness to see yourself in a new way.

What’s been the best source of new clients for you?

The strongest source of new clientele for me has been word-of-mouth referrals and the relationships I’ve built over time. A large portion of my work comes from clients who have experienced my styling process firsthand and then share it with friends, colleagues, or within their own communities.

I’ve also intentionally immersed myself in smaller, local networking groups where women can really understand what I do and confidently refer me within the community. Like many counties, we have active Facebook community and mom groups, and being present and consistently referred in those spaces has been incredibly impactful. From there, potential clients are able to easily book a discovery call, and I have a very strong close rate when it comes to on boarding new clients.

Social media also plays a supporting role, especially Facebook and Instagram, where people can see real transformations, client stories, and how I approach styling in a practical, wearable way. But at the core, it’s always been trust and relationships that consistently bring in new clients.

Any stories or insights that might help us understand how you’ve built such a strong reputation?

My reputation has been built through consistency, strong customer service, and making style feel approachable rather than intimidating. My background in customer service has deeply shaped how I deliver my work and stay connected with clients. I often say everyone should work in a restaurant at some point in their life. I started as a hostess at fifteen, which taught me early how to show up for people, read needs quickly, and stay composed in front of customers. Service has always been my foundation.

Looking back, many of my early roles helped build the skill set I now use in my business. I didn’t know it, but the small stints in retail and over a decade in hands-on accessories work, to a bachelor’s degree in media production and experience in customer-focused apparel companies, each step contributed to how I understand both people and deliver solutions.

I’ve carried all of that into my styling business by really listening, following through, and helping women feel seen throughout the process. I’m also known for showing up vulnerably online, and interestingly, many women have shared that my sobriety story, not just my styling work is what initially drew them to me and made them feel connected enough to reach out.

Contact Info:

• Website: https://www.ashleylayres.com
• Instagram: @collectivelystyledbyashley
• Facebook: https://www.facebook.com/AshleyAyresCollectivelyStyled

Image Credits

Elle Yeon Photgraphy https://elleyeonphotography.com/