Deepening a Connection to Our Personal Style
with Caroline Rooney
Caroline Rooney has built a stylist career by choosing the fashion road less—if ever—traveled. While growing up in Michigan, she started modeling at 14. “My parents pitched it as ‘you can model as long as you stay in school and it's not the only interesting thing about you,’” she says over Zoom. This remark wasn’t meant to cast shade but rather a light on all there is to consider in the world—which Rooney was inclined to see. “From the very beginning, this holistic understanding of the fashion industry was important to me,” she says.
This curiosity soon unspooled into entrepreneurship. As a college student at the University of Michigan, Rooney created a t-shirt company. These were not your run-of-the-mill cotton cuts: Each design was linked to a non-profit to which she gave a portion of sales, an effort she says was to “combine a sense of community and give back.” The collection was so successful that Rooney’s post-graduation plan was to move to New York City to continue modeling and running her company. But just like that, she found herself pivoting. She closed her t-shirt company and stepped away from her modeling contracts to accept a position in buying at Bloomingdale’s—a strategic move to learn yet another side of the business. “It was an exciting time to be there,” Rooney says of the role, which, in her two-and-a-half years in the position, took her to her first fashion week and into the emerging worlds of e-commerce and fashion influencers.
Not long before she departed Bloomingdale’s, a realization emerged for Rooney: She missed running her own company. At the time, she was regularly traveling cross country to see her then-boyfriend (now husband) in San Francisco. “There was this big gap in the market,” she says, referring to the Bay Area’s inhabitants. They “were interested in aesthetics, but didn't always prioritize getting dressed.” The city also boasted “amazing resources and boutiques.” The thought of merging these elements created an allure. “The more I was going out to San Francisco, I realized, what a cool opportunity for me to bring my experience from New York to the Bay?” This question—which Rooney asked herself more than eight years ago—spurred a life-changing decision. She left her job and moved to San Francisco to start her new life and burgeoning styling business.
Each of these measured career twists and turns imbues in Rooney a deeply layered view of fashion and aesthetics—which she brings to her work as a personal and commercial stylist today. She considers everything when she’s creating a look: A person’s history, inclinations, even dreams.
From her home in Mexico City, where she now lives with her husband and their new baby, and where she will soon be opening her boutique, Kingfisher, Rooney indulged us on her storied career and how she approaches styling with such depth. As her insights illustrate, to define her work would be akin to describing a storied tapestry: There are textures and narratives, all boasting of nuance and interlocking to create a body of work anchored in beauty and propelled by intention.
A Conversation with Caroline Rooney
When you took the plunge to start your styling business, there were many elements at play. What was driving you?
I wanted to build a career that I could manage and that was—first and foremost—about making people look and feel their best. I thought: How could I do that while also leveraging my expertise in fit and color and texture and pattern and all of that? And so, I quit my job in New York, sold all my furniture, and was on a plane to San Francisco in two weeks. Then I started my company. It was a huge leap of faith, but one of the best decisions I've ever made. I love being an entrepreneur and a business owner because you can dictate what that looks like—and you can make it your own. I've taken long-term projects and done more freelance work. I’ve worked with amazing private clients, and I've also done commercial work where you’re pulling all-nighters on these huge sets. This hits all different parts of my personality. It's been a fun adventure and I'm proud of it.
Hearing this serves as a reminder that we can architect the careers we want rather than feel we must follow a conventional path.
There's so much power in building a life of your own, even that if it doesn't make sense to anybody else. It makes sense to you, and this is what you want, that's freeing. When I was 18, I thought I wanted the corner office at a big fashion company. Now I look at my life and it couldn't be more different and I couldn't be happier. There's just so much power in that for me. It also gives you an edge in your work. I come to my clients with experience across markets and across demographics. To me, that makes it more interesting and I'm better able to serve them. For them to wear a certain garment means something different. I need to be able to put myself in their shoes and not come at things with this big fashion, New York, everything-has-to-be-fancy-and-from-a-certain-designer kind of aesthetic. That's not how I run my business. I'm not walking into a client and saying, ‘you have to wear this because this is what's on-trend.’ It's about making them look good and feel confident.
Style is so incredibly personal. When you start working with a new client, how do you create a connection?
We always joke that I'm like a therapist to my clients. I always invite a potential client out to coffee. It's a complimentary first one-hour meeting, and I say, ‘okay, we're going to get to know each other.’ We need to make sure that we trust each other, that we respect each other, and that we have the same goals in going into this. The questions I ask really range and include: Who's your style icon? What would you never wear? Is there a brand that you think is interesting? Where do you hang out? Where do you go up to dinner? Tell me about your partnership. Do you have kids? Where do you vacation? I want to get a strong sense of what you value and what makes you tick. It’s funny, I feel like my clients, who are all incredibly successful and intelligent, start to open up. It's interesting to see them self-reflect in having to answer these questions that they've likely never considered before.
Sometimes fashion and personal style can be seen as frivolous for those outside the industry. What realizations around this have you helped people to see?
Absolutely. Especially when you have spent so much of your career building a business that is not a fashion industry adjacent. There’s what I call a ‘reverse pretentiousness’ around it; this idea that caring about what you wear is vapid. I like to debunk that. How you look is important. How you put yourself into the universe is something you control. It’s a very individual choice of how you want to show up in the world, how you want to show up at your company, how you want to show up as a leader. The confidence element is also really very important. So much of what I do as a stylist is about elevated basics. A client comes to me, and I tell them that we need to build a wardrobe of high-end beautiful, well-fitting garments. Not because they're expensive, but because they fit well, they look great, and they help you feel good. Then we layer in color and patterns and things that make them feel more unique to their personality. And if they like trends, we pepper in a few trend pieces. But the core of it should never be about the clothes. When a client of mine walks into a room, I want them to lead before the clothes.
What is your advice to someone who is looking to discover their style?
There’s this idea that fashion is scary and intimidating. And sometimes it can be. You may walk into a boutique and think, this is so overwhelming. But what I would always encourage someone to do is to go through their wardrobe and pick out the thing that if they had a huge job interview or a big date, they would choose to feel their best. That’s very telling. If they picked a structured blazer and a heel, I would say latch on to those things and stay within that wheelhouse. For me, I love structured blazers. I own probably 30 of them. That's my power item. A lot of times people get caught up in what is cool and trendy when at the core of what you should be thinking about is what fits you, what feels good, and what compliments you and your body type. That is why I always encourage people to focus on those well-fitting beautiful pieces that fit them uniquely. That's why I love Lan’s designs. Those kinds of pieces that are beautifully made, with care, intention, and beautiful fabrics, are the cornerstone of a well curated wardrobe.
What are some parallels that you see between Lan Jaenicke and your work?
We can get caught up in this idea that we must have a lot of stuff. Something I encourage all of my clients to do is work with a good tailor. You want your garments to fit you perfectly so you can confidently wear them many times. Lan is so good at prioritizing fit in her pieces. I’m always so impressed by her willingness to alter a piece to best fit her client.
I've also seen the market shifting away from this massive consumerism, which I think is healthy. I will sometimes hear from my clients about certain items that I choose being expensive. But I'll say, ‘Do you love it? Are you going to wear it every single day? You could buy six sweaters that you don't really like and will donate in six months, so I’d rather you have this one sweater that you love and will wear.’ As a consumer, you should have an edited assortment of things that bring you joy and make you feel good. Lan designs the perfect capsule wardrobe. I love taking my clients to [The Atelier]. Walking into the space they’ll say, ‘this the most beautiful place.’ There's a calm assuredness to Lan and her clothes that is hard to find. People really value that.