Margaret's Cover Interview with Kentfield & Ross Living

Margaret O'Leary' cover image on Kentfield & Ross Living Magazine. She sits on a yellow armchair in her Marin home.

Margaret O’Leary: Touch and you Fall in Love

 As interviewed by Mickey Nelson | Photos by Laura Kudritzki Photography

Margaret and her husband Bill sit at their dining room table and cheers with two glasses of wine.
 Irish-born Margaret O’Leary grew up on a working farm in County Kerry and first discovered fashion as a child, when she had to dress up for church on Sundays. She is the second oldest of 12 children. When I ask about her family, “Who can remember all their names, let alone birthdays?!” she quips. You’ll see that this sort of charming sass is common—and suiting—the respected clothing designer with dark hair and bright, twinkly eyes.

From her rural roots in Western Ireland all the way to dressing the likes of Oprah and Gwyneth, Margaret has stayed true to her brand’s mission of quality material and incomparable fit. In looking at her business success,
it would be understandable if Margaret had time for little else, but that’s not the case. She is a diehard music fan (“We’re deadheads.”), a connoisseur of spatial décor (“I especially like Chinese Art Deco Style rugs.”) an international foodie, a charitable worker on behalf of women and children...and so much more. What you see when you see Margaret is a woman with a full, vibrant life and a generous spirit.

n leaving our (ridiculously fun) photoshoot one weekend, I had to ask this famous lover of color which is her favorite. “Definitely some shade of blue...but I also like pink... to make the boys wink,” she says with a wink.

MN: Hello, Margaret! I am so honored to have you here today and selfishly, that this interview process has made you a friend!
MOL: Mickey, the honor is all mine...what a pleasure to meet you!

MN: You have a big name in clothing. First off, can you tell us how you got into the field?
MOL: I have loved clothing and dressing up since I was a child growing up in Ireland. (Although I didn’t have much chance to do it, as I’ll explain later.) For me, it is a delight to explore new colors and textures as I design a new collection each season. I communicate how I feel by what I wear, and I love providing that experience for others. I fell into this business by accident and I love it. I say, do what you love and the rest will follow.

MN: I am also Irish! What part do you think your Irish heritage plays in your stores and design?
MOL: Growing up on a farm in rural Ireland, the one big occasion to dress up was Sunday Mass. All the best fashion in the town was on display at church. But on the other six days, we looked like the poor farmers that we
were, with wellington boots and old, darned sweaters and So, the dress up ritual became a runway opportunity as we went down the church aisle to receive Holy Communion! So, fashion shows began in Catholic church for me every Sunday.

MN: When you came to the US, did you hop right into being Margaret O’Leary?
MOL: Yes! I’ve been in this country for 30 years and have only had one job... this one. Of course, it has changed a lot over the years. When I started, it was making hand loomed sweaters in my apartment in the Richmond district of San Francisco, going from boutique to boutique, selling my sweaters. I opened my first store in SF, then made my way to Marin and the never looked back.

MN: So, what is your role in the company? Tell us about what it entails on the day-to-day?
MOL: I am the CEO and Design Director. The team meets every day in our San Francisco offices and I spend most of my day in the Potrero Hill design studio with our Team conceptualizing the new design menu, so to speak. We plan ahead, given the complexity of sourcing organic fibers so, believe it or not, we are designing Fall 2023 now!

MN: And you’ve survived the pandemic. What was it like being a business owner during COVID?
MOL: It was nerve-racking to have to close all 14 stores and head office and figure out how to pay rents, payroll and that Spring 2020 inventory. Staying afloat and taking care of our people was top of mind. Office workers somehow pivoted easily to Zoom, but this clothing business didn’t really adapt to Zoom. Also, people started kicking back in sweats all day as there was nowhere to go! Our website did help some, but our customers seem to be the “touch, feel, love, buy” type and I am thrilled that we survived and are now slowly making our way back!

MN: Speaking of touching and loving, I got to spend the day in your store with you and your sweaters are just the most luxurious-feeling pieces in the world. I love the idea that you name some of them after saints. How did that begin and why do you do it?
MOL: I’m a lapsed catholic. After growing up saying the Rosary every night and years of Sunday Mass, this Catholicism is kind of hardwired in my psyche. I started making a super pricey 4-ply cashmere coat-sweater called the St. Claire and could not believe how many people bought it, so I started naming the expensive pieces after saints, hoping that God would bless every wearer... and I swear it happens! Check out my newest Saint, the Saint Bridget, in stores.

MN: I believe it! I certainly feel blessed rocking my MOL sweater. Are there any moments in the store’s history that stand out as your biggest accomplishments?
MOL: Anytime a customer buys anything is a moment of celebration and gratitude for me. Of course, it was fantastic to get my first order from Bergdorf Goodman in New York, as I felt I had ‘arrived,’ but I appreciate every single interaction with our clients, to this day.

Margaret stands next to a table display in her Mill Valley store.

MN: How about lessons you’ve learned from instances that were more trying in growing a business?
MOL: Many people yearn for a career in the fashion industry. They are taken by the glamour and allure of this profession. After 30 years, I have learned that the hardest part of this business is not the design (either they come to you or they don’t!), but the management of the intensely complicated business. First we design, then we source, then we fit (the most important part to us), then we produce... then we manage the operations. Creative is fun— kinda’ like being in the doll house—but keeping tabs on the financial part is like doing the’s gotta get done but one may not love it.

MN: Well maybe something a bit more fun...I read on your LinkedIn the list of celebs you’ve dressed! That has to be exciting.
MOL: It’s fun when a celeb wears the clothes. I like turning on the TV and seeing our products on Jane Fonda, Gwyneth Paltrow, Oprah, Kerry Washington or whoever. I am always a little surprised and impressed, like, “Wow, we made that!”

MN: What are your goals for Margaret O’Leary—the company?
MOL: After 30 years, we have turned our gaze toward sustainability... and I don’t mean of our products and processes, although that is integral. I mean of the company and the Brand. Although my name is on the door, we recently became an ESOP (employee-owned) company, and my role now is to empower my Team to grow the business for another 30 years! We currently have 14 stores in the US and I’m always thinking about where we could open next. Generally, our customers lead us to the answer when they write and say, “How about coming to Atlanta or Miami or Dallas, Margaret?” We recently opened in Edina, Minnesota and it has been successful. We seem to like those cold places!!

Margaret works on a sweater design at her San Fransisco design studio.

MN: And what are your personal goals for Margaret O’ Leary— the person?
MOL: I won’t tell you how young I am but people around me seem to be slowing down and simplifying their lives, while I drive to the City every day. I just love creating and sharing clothes that make people smile. You’d be surprised how often people stop me in the street or in one of the store and say, “I have had this sweater or pant for a decade and it’s my favorite thing to wear!” How do you walk away from that?

MN: With regard to the larger retail picture in our world today, how do
you think it has changed?
MOL: Now, everyone has pivoted to omni-channel shopping, so people can essentially shop the whole world online. We have amplified our web presence, but we try to merge the virtual experience with brick-and mortar so that our customers can preview online and shop in store (or vice-versa). We have worked out these logistics and now our customers are omni-shoppers.

MN: What do you notice about Marin clothing style? Has that
shifted since you opened?
MOL: It’s certainly more casual, and this trend began well before people started working from home. We call our look ‘California Chic’ because I believe it is important to feel good and look good at the same time. People in Marin enjoy what we call ‘hybrid dressing’ with outfits that allow them to transition from the gym to work to food shopping. I often see Lululemon leggings paired with a lux Margaret cashmere sweater...The classic Marin uniform.

MN: Let’s talk about giving back. Can you tell us about your philanthropy work?
MOL: I have been active with various philanthropic causes since I first made a little money, and it seems like part of my calling. I am passionate about helping women and children and have supported various breast cancer research charities as well as the local food banks. It’s surprising how many people in Marin need help, and I always try to be there in some
small way.

MN: Alright, on to some more personal questions...though I know you treat your work personally! Tell us about your family life.
MOL: I live in an old house in downtown Mill Valley with my husband, Bill, who is a climate crusader and has been active in alternative energy and related fields for decades. We try to find an hour to hike every afternoon after work and share our day of challenges and triumphs. We raised three boys together (who went to Mill Valley public schools) and they are all out of the house and ‘off the payroll’ – which we consider a significant

Margaret wearing a bright pink cashmere cardigan and standing in front of her garden.

MN: What do you do for fun? What does a typical weekend look like?
MOL: We work pretty hard, so the weekends can be meetings and emails, but we do hike every weekend. Tenderfoot trail a favorite as are the Dipsea and Sun Trails. We love our e-bikes and go from Mill Valley to Tiburon and over the Corte Madera Hill for a great 28- mile loop. Then a bit of gardening and house stuff (never ending) and dinners with friends. Thankfully, Bill my husband, is a foodie and likes to cook and all I have to do is clean up! On evenings out, we love our favorite local establishments— Sweetwater for music and the Throckmorton Theatre for Comedy. La Ginestra, Tamalpie and Watershed are our regular spots for food.

MN: Speaking of food...In addition to everything else you do, you and your husband travel the world for the best restaurants. What country has the best food? Do you two like to cook together or experiment in the kitchen here in Marin as well?
MOL: Yes, indeed I married a foodie and should probably weigh 2,000 lbs! We love France more than any other country for the food across the board (from country cuisine to haute cuisine in Paris), but recently found that Copenhagen is the most innovative food city, spawned in large part by the Noma Chef Rene Redzepi. He is the mad scientist of food and has fermentation labs dedicated to creating flavors that you could only  imagine—maybe not even in a dream! As for my part in home cooking, well...I’m the kitchen slave doing all the set up and I feel I should get a Michelin star for cleaning up Bill’s messes, but his cooking is great. Every rose has a thorn, I suppose.

MN: I had the pleasure of visiting your exquisite Mill Valley home. Can you tell our readers a bit about it?
MOL: Our house is one of the original Mill Valley homes in downtown. It has become a lifelong restoration project and there is no end in sight. It is an old-world house (Greek Revival), updated with lots of color and charm. Objects from the Alameda Flea Market are mixed in with mid-century to give it a unique charm. We collect Astier De Vilette pottery and Art Deco Chinese rugs from the 1930s. We collect pieces that we both believe are beautiful and functional at the same time. As you might guess, I am a lover of color and fabric in the home. (Spoiler alert: you may be seeing some of those pieces in a new Margaret O’Leary Home collection one day soon!)

MN: That will be a heard it here first! I noticed lots of Rock ‘n Roll photography on your walls! Not to mention the David Bowie scarf in your store! You say you are a Deadhead. Tell us about your love of music.
MOL: Hmm, well I married a deadhead and Bob Weir officiated our wedding in the backyard, which was pretty great. If you’ve never seen the Dead live (now Dead and Company), you have been missing out. A Dead show is like no other and now that John Mayer is playing with Dead and Company, it has a new trajectory. There is often a “shopping event” associated with these shows called Shakedown Street, which is effectively an old hippie street market that I love going to. It gives me the latest tie-dye inspo, believe it or not. As for the rock ‘n roll photography, Bill’s first career was as a photographer and he has some great photos of The Who, Clapton and musicians of that genre.

Margaret holding a printed scarf in her Mill Valley store.

MN: This is all just so awesome, Margaret. You have any outside talents or hobbies you love to do?
MOL: I am a big Pilates and Gyrotonics devotee and, there is a fantastic studio called Fitwise just minutes from my house. We do like to travel, especially to Europe. I love Copenhagen and Paris and of course the old country Ireland. I suppose wanderlust is something I am both good at and has become a hobby and passion!

Margaret, age 9, in Ireland with 2 siblings. Sweaters knit by her mother, who taught her knitting.

MN: How do you participate with your community?
MOL: We have been sponsoring so many Mill Valley and Marin events over the years. Parades, fashion shows, junior sports and events for kiddos. It’s always been important for me and the Company to maintain and grow strong ties to our Marin home and be entwined in the community.

MN: What do you love most about living here? In Marin at large?
MOL: I love the outdoors. Marin is my inspiration, and I design around the Marin lifestyle. It’s great because those designs seem to work in so many other places, but make no mistake, Margaret O’Leary is born, bred and raised in Marin County California! Redwoods, fog and mist, all the way!