Finding clothes that fit is one thing. Finding clothes that make you feel comfortable, confident, and genuinely yourself can be much harder.
In my latest LUXEtalk conversation, I spoke with Kate Breen of Get Dressed Go about personal styling, the emotions behind our clothing choices, and how she transformed her passion for fashion into a growing business.
As a luxury real estate broker, I understand how personal presentation can influence confidence in professional settings. On LUXEtalk, I explore the experiences of entrepreneurs whose work offers practical lessons for everyday life and business.
In this conversation, you’ll learn:
- How Kate built her styling business from a side hustle.
- What separates an excellent personal stylist from a good one.
- How clothing choices can influence confidence and self-image.
- How to find a stylist who understands your individual needs.
- Why listening to clients can help a service business grow.
Check out the highlights here:
Why I Had This Conversation With Kate Breen of Get Dressed Go About Personal Styling
I’ve always believed that feeling comfortable in what you’re wearing can make a difference in how you carry yourself.
That’s why I wanted to speak with Kate, the founder and lead stylist of Get Dressed Go, a collective of private personal stylists in the Washington, DC area.
Her experience working in fashion, theater, and corporate environments gives her an interesting perspective on what people need from their wardrobes.
What interested me most was her belief that excellent styling begins with understanding the person wearing the clothes.
Watch the full conversation here:
How Kate Breen Turned Get Dressed Go From a Side Hustle Into a Styling Agency
Kate’s personal styling business began with years of experience working with clothes and an unexpected advantage from her corporate career.
For approximately a decade, she worked in administrative positions at global law firms and a hedge fund. Working around executives helped her understand their schedules, professional responsibilities, and attitudes toward clothing.
She recognized an opportunity to help busy professionals who lacked the time or interest to manage their wardrobes.
Starting With a Simple Idea
In February 2021, Kate launched Get Dressed Go while maintaining her full-time job.
She created a website, gave the business a name, and announced her services on Facebook. Friends, family, and referrals became her first sources of clients.
Demand grew quickly.
Two early clients who advised small businesses suggested that her overwhelming workload might indicate her prices were too low.
Kate followed their advice, raising her prices as she refined her services.
When she later lost her corporate job, she decided to pursue styling full-time.
Growing Beyond One Stylist
After approximately three and a half years working independently, Kate began thinking seriously about expansion.
She realized that several talented stylists she had mentored enjoyed styling but didn’t necessarily want to operate their own businesses.
“Just because you’re a stylist doesn’t mean that you’re an entrepreneur. And that is why these three particular women have all this talent. And I’ve been so confused about why are you not going out and doing this on your own?” — Kate Breen, Founder and Lead Stylist of Get Dressed Go
She invited them to work under the Get Dressed Go business model while receiving deeper mentorship.
Her experience offers a valuable lesson for anyone building a personal styling business or another service-based company: growth can come from developing other talented professionals.
But business growth means little without the client experience that makes people seek out your services.
What Makes an Excellent Private Personal Stylist?
When I asked Kate what separates a good stylist from an excellent one, her answer centered on understanding individuals.
She explained that department store stylists, photoshoot stylists, and private personal stylists often perform different roles.
For Kate, excellent private personal styling requires learning about a client’s finances, family background, experiences with clothing, and lifestyle.
Her recommendations reflect that understanding.
Expertise Beyond Fashion Trends
Kate emphasized the importance of knowing garment construction, fit, fabric, and fashion history.
A stylist should understand whether clothing will last, how it fits different proportions, and whether a particular design suits someone’s needs.
Kate believes this arrangement supports client trust because recommendations can come from multiple shopping resources without brand-commission incentives.
That approach is specific to her business, but it raises a useful consideration for anyone hiring a stylist.
Before choosing one, understand how they select clothing and what influences their recommendations.
That level of trust becomes especially important when clothing is connected to someone’s confidence.
How Personal Styling Builds Confidence by Understanding the Person Behind the Clothes
She developed a detailed client questionnaire that examines experiences stretching back to childhood.
She asks about family attitudes toward dressing well, previous shopping experiences, and memories associated with feeling confident.
Finding the Feeling Behind an Outfit
Kate often asks clients to remember a time when they felt wonderful in their clothing.
“It doesn’t matter how long ago it was, I want to hear about it. I want to hear about the dress. I want to hear the story. I want to hear about how you felt because that’s what we’re going to recapture together.” — Kate Breen, Founder and Lead Stylist of Get Dressed Go
For clients who cannot recall such a moment, Kate explores other experiences, including favorite music and vacations, to understand the feelings they want their clothes to create.
She also recognizes how changing bodies and disappointing shopping experiences affect confidence.
During our conversation, I observed that her approach explores some of the emotional and psychological dimensions of clothing. Kate acknowledged the vulnerability involved while making clear that she isn’t a therapist.
Her goal is to help clients identify clothing that feels right for them.
For someone struggling with their wardrobe, remembering a favorite outfit may be a useful starting point.
That personal understanding should also influence which stylist someone chooses.
How to Choose a Personal Stylist Who Understands Your Needs
When I asked Kate how to choose a personal stylist, she recommended starting with a local search for private personal stylists.
From there, she encouraged people to consider each stylist’s personality and process.
An attractive portfolio may catch your attention, but Kate cautioned against choosing someone simply because you want to copy how they dress.
She prefers adapting to each client’s individual energy.
Questions to Ask Before Booking
Consider these five questions when evaluating a stylist:
- Personal connection: Do I feel comfortable discussing my wardrobe concerns?
- Discovery process: Will this stylist ask about my lifestyle and preferences?
- Clothing expertise: Can they explain fit, fabric, and construction?
- Shopping flexibility: Can they recommend clothing from different sources?
- Educational value: Will I learn skills I can use independently?
These questions help clarify whether a stylist’s approach matches your needs.
And that last question leads directly to another idea Kate emphasized throughout our discussion.
Why Kate Breen Treats Personal Styling as a Skill You Can Learn for Life
Kate approaches styling as an educational experience.
She explained that most people cannot afford to work with a private stylist repeatedly throughout their lives. Her goal is to help clients build practical skills they can continue using.
Get Dressed Go offers comprehensive styling packages designed as a structured experience.
These sessions begin with a questionnaire and can address concerns such as shopping effectively, finding inspiration, or dressing for photographs.
Learning From the Dressing Room
Kate shared how frustrating it can feel when an outfit looks disappointing after you’ve been excited to try it on.
Her advice involves taking time to understand what isn’t working.
For example:
- Try a belt or consider alterations before rejecting a garment.
- Explore brands designed for different body proportions.
- Pay attention to recurring fit problems.
- Learn which silhouettes you enjoy wearing.
- Use unsuccessful purchases to make better decisions next time.
Kate even admitted that certain fashionable puff-sleeve dresses consistently failed to work for her own proportions.
That experience reinforced her empathy for clients facing similar frustrations.
The objective is to help people make more informed clothing decisions long after their appointments end.
Interestingly, Kate applies a similar learning mindset to running her business.
What Kate’s Experience Taught Me About Building a Purposeful Business
Kate’s expansion also required her to reconsider some original assumptions.
When she introduced additional stylists, she assigned them to client niches based on her experience in the Washington, DC market.
But prospective clients didn’t always choose according to those categories.
Instead, many responded to a stylist’s personality and the connection they felt.
Kate reviewed what was happening and changed the website and stylist-selection process.
She reported that inquiries and bookings increased significantly afterward.
Letting Client Behavior Guide Decisions
Her experience illustrates three useful business practices:
- Start with a clear plan. Know whom you hope to serve.
- Observe real behavior. Pay attention when customers make unexpected choices.
- Adjust your process. Make changes based on what clients actually need.
I also enjoyed hearing about Kate’s new studio in Old Town Alexandria, Virginia.
She described an inspiring space for styling appointments and team collaboration, with plans to develop small-group sessions and classes.
Those planned learning opportunities reflect her broader vision of making styling knowledge more accessible.
What Changed for Me After This Conversation
My conversation with Kate expanded how I think about the connection between clothing and confidence.
I already appreciated how feeling well-dressed can influence someone’s presence, especially in professional environments.
What stayed with me was Kate’s willingness to explore the memories, experiences, and personal preferences behind those feelings.
I also appreciated her philosophy of teaching clients to make their own clothing decisions.
And from a business perspective, her story demonstrated how mentorship and careful attention to customer behavior can create opportunities for growth.
Whether you’re developing a wardrobe or building a business, understanding the individual matters.
Frequently Asked Questions About Kate Breen and Get Dressed Go
Who is Kate Breen of Get Dressed Go?
Kate Breen is the founder and lead stylist of Get Dressed Go, a Washington, DC-area collective of private personal stylists. She expanded her business from a side hustle into a multi-stylist agency.
What services does Get Dressed Go offer?
Get Dressed Go provides comprehensive personal styling packages and individualized one-hour virtual sessions. Services focus on client preferences, wardrobe challenges, and practical styling education.
How do I choose the right private personal stylist?
Kate recommends finding someone whose personality and process feel comfortable. Look for a stylist who takes time to understand your lifestyle, existing wardrobe, and personal concerns.
Can personal styling help improve wardrobe confidence?
Kate’s approach helps clients understand what makes them feel comfortable and confident. It also teaches practical ways to evaluate fit, shop more effectively, and work with different body proportions.
How did Kate Breen grow her personal styling business?
She launched Get Dressed Go in February 2021, attracted referrals, adjusted pricing as demand increased, and eventually transitioned into full-time styling. She later expanded by mentoring additional stylists.
Keep the Conversation Going
If you want to understand your wardrobe better and make clothing decisions with greater confidence, follow Kate and explore her approach to personal styling.
Connect with Kate Breen:
- Website: Get Dressed Go
- Instagram: @get_dressed_go
- LinkedIn: Kate Breen
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Follow Lisa Berg:
- Website: Lisa Berg Real Estate
- LinkedIn: Lisa Berg
- Facebook: Lisa Berg Real Estate
If you’re exploring real estate in Whatcom County, you can also discover luxury properties, explore my resources for home buyers and home sellers, or meet my real estate team.
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Kate’s story reminds me how valuable it is to hear from professionals who have built meaningful businesses through experience, creativity, and a genuine understanding of their clients.
If you’re an entrepreneur, business owner, or professional with lessons worth sharing, I’d love to spotlight your insights on LUXEtalk.