We recently connected with Kevin Ann Jordan and have shared our conversation below.
Kevin Ann, thanks for taking the time to share your stories with us today Let’s start with a story that highlights an important way in which your brand diverges from the industry standard.
As a personal stylist, there are no specific industry standards, which is both awesome and challenging. With the rise of personal styling companies, like Stitch Fix, Trunk Club and Wishi, there is a more trend-focused, fashion-forward norm of personal styling – it is expected that your personal stylist helps you buy new clothes more than wearing the clothes you already own.
With more than 70% of donated clothing ending up in landfill, I decided early on in my business to move away from the trend-focused, fashion-forward, consumption-based model that I had learned while working as a remote stylist at Stitch Fix in the company’s early start-up years. I loved the company ethos of empowering women to feel their best, but I struggled with the amount of clothing women were consuming – I believe most people don’t need five new pieces of clothing each month.
Of course, everyone needs to buy new clothes, shoes and accessories on occasion, and I am not immune to the consumer society in which we live, however, I use a slow-fashion, style-conscious, intentional approach with my clients (and my own wardrobe).
I believe that by slowing down and considering our own personal values, preferences, lifestyle, and wardrobe needs, we can curate our wardrobes in a way that is thoughtful. I help women discover their own personal style – words that are meaningful to them – rather than boho or chic or glamorous. I call this a Style Manifesto and it is the basis for a thoughtful approach to style and fashion.
With her Style Manifesto in hand, we explore her closet – both cleaning it out and editing it so that it is a delightful space in which to inspire her daily dressing. We fill in gaps with new or secondhand clothes, focusing on companies that produce in a way that is kind to the planet, people and animals. Lastly, we style looks that align with her real life – for events, date nights, work presentations, kids’ sporting events and family vacations – so that when it comes to getting dressed, she never again stands in front of a full closet feeling like she has nothing to wear.


Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
Have you ever stood in front of your closet, filled with clothes, and felt like you have nothing to wear?
It is a common experience that most people can relate to – we all have to get dressed to some extent each day! This whole question of “what should I wear” can be a stressful way to start the day.
I help women simplify getting dressed so that they feel confident that their outsides match their insides. Along the way, I educate and inspire women to curate their wardrobe in a way that is thoughtful and kind to the planet, people and animals.
My Style Transformation package is a four-step process that starts with creating her Style Manifesto. During this initial step, we set goals and align her style with her values, lifestyle and preferences. From there, we clean out her closet and edit it – that means we part with clothes that do not match her Style Manifesto and we make a shopping list for pieces that will make getting dressed easier. We thoughtfully donate, recycle and reuse pieces that she doesn’t keep (and for virtual clients, I provide guidance on what to do with unwanted items). Step three is strategic shopping – we maximize her budget and prioritize quality over quantity to add items to her wardrobe that will improve her style, not fill up her closet. Along the way we talk about styling and how to wear her clothes and in the last step, we create outfits that she can reference and wear repeatedly in her life! The transformation takes at least 6 weeks, with most women preferring a slower approach of eight to 12 weeks.
On transformation, I encourage her to join my Sustainable Style Club (a monthly membership) so that we can be in touch regularly as she becomes more comfortable with her style. We often update her wardrobe seasonally as preferences, lifestyles and wardrobe needs change over time. I offer Seasonal Updates to existing clients to keep their closets edited and current.
I offer an experience that is judgment-free, empowering and thoughtful – I encourage my clients to let go of consumer pressures and to rediscover themselves as part of their transformation. Ultimately, our clothes should work for us, not against us – and it is possible to curate a beautiful wardrobe that is kind to ourselves, the planet, people and animals.

What’s worked well for you in terms of a source for new clients?
For me, the best source of new clients are referrals – women love helping other women and so many of my clients have become champions for me – sending their friends and family to me. I’m so grateful to have had clients in San Diego, and all over the world, thanks to my clients who have shared their experience working with me. My referral program offers current clients complimentary styling time – we all benefit from this arrangement!
I also work with photographers in Southern and Northern California – we send each other clients – everyone wants professional photos these days. If you’re going to invest in the photographer, it is worth making sure you are wearing clothes that make you feel your best. For photoshoots, we always shop a client’s closet before buying new clothes – that way they feel like themselves and any investment in new clothes will become a part of their wardrobe rather than a piece that has to be returned later.
How about pivoting – can you share the story of a time you’ve had to pivot?
I met my husband when I was studying abroad in Sydney, Australia. I loved it there so much that after I finished my university studies, I returned to Australia and stayed for the next 10 years! When we decided to move back to California, it was hard to translate the healthcare policy consulting work I was doing to the West Coast. I ended up burning out in the pharmaceutical industry, which led me to my creative outlet of styling – it was risky to pivot from the corporate career I had built but it has been so worth it from a mental health and family perspective – plus I never thought I would own my own business and get to help women look and feel their best!
This pivot might seem like a sharp turn, but I learned so much in my corporate career that has helped me run my own business. Professionalism is something that my clients really value and I want to offer the best experience for them – going into a woman’s closet is a personal experience – sometimes working in her closet turns into therapy. Discovering herself and her style is something that many women haven’t done before and I’m so grateful to have the opportunity to guide them through their transformation.
Contact Info:
- Website: tailoredstylist.com
- Instagram: instagram.com/tailoredstylist
- Facebook: facebook.com/tailoredstylist
- Linkedin: https://www.linkedin.com/in/kevinannjordan/
Image Credits
Melinda Humphries Greta Dunn Photography
