by Whitley Adkins | photographs by Amy Kolo
Perhaps best known for her abstract portraits of women she calls “Chicas,” Charlotte artist Windy O’Connor was drawn to the creative arts at an early age.
“When I started taking art classes, my brain and my soul lit on fire,” says O’Connor, who studied interior design and minored in business and theater design at East Carolina University. “I’ve always been creative since I was a tiny child.”
The Fayetteville native moved to the Queen City 34 years ago with her husband, Blake, who worked in banking. In Charlotte, her passion for art and design exploded into an entire lifestyle brand which includes textiles, wallpaper, clothing and home accessories.
Aside from her art career, anyone who knows O’Connor personally or follows her on Instagram recognizes her equally innate, if not trendsetting, proclivity for fashion and style.
We visited Windy at her home — the carriage house of the 1927 Morrocroft Estate in SouthPark — for a peek inside her aesthetically-pleasing-at-every-corner home and en-suite closet.
Comments have been edited for length and clarity.
PERSONAL STYLE
When did you start liking fashion? I don’t remember ever not liking fashion. I have pictures of me around age 4 at Christmas, and the look on my face as I’m putting on my little white leather gloves said it all — it was love at first sight. I remember caring about my bobby socks and Mary Jane shoes going to church when I was 3.
How do you describe your personal style? Classic, creative, humorous. There’s always some unexpected twist or element. I’ll take one thing and wear it 20 different ways.
How has your style evolved over time? As we grow and age, how we dress our bodies and our lifestyles change. So I probably have more black in my wardrobe than ever before, because I love to travel and it is the easiest way to pack for a trip. I would never say I’m a minimalist. If I’m doing neutral colors, I’m still a maximalist.
Your followers are really into your personal style — I feel like your Instagram has become a part of your brand. It has allowed me to connect with people all over the world — it has been so much fun. I would wear my normal clothes (not just my overalls painting), and people would ask about my outfit. One time someone asked about my shoes — I wasn’t wearing any.
Is there overlap with your fashion sense and interior-design style? Yes, color in my wardrobe, in my home. Color makes you happy. It influences your emotions and energy, attitude — all those things.
How does what you paint and design translate into what you wear? I’ll use elements of something I see in fashion design in a painting, or even a certain vibe. I just finished an art piece that is so similar to a pair of pants I have, and I never thought about it until just now.
Do you have a formula for getting dressed? Lord no! If only. I like experimenting in my closet. It’s like mixing paint.
You’re doing this really cool athleisure thing. Tell us more. I will say, I’ve seen elements of that out and about, little murmurings of sportswear as fashion — people wearing bathing suits, board shorts or surf pants with a sequin top or something dressy.
SHOPPING + STYLE ICONS
Style icons: Blanca Miro Scrimieri, Vicky Montanari, Laurel Pantin, Leandra Medine Cohen, Sarah Corbett-Winder.
Favorite designers: The Olsen twins and The Row, Khaite, Celine, Rosie Assoulin, Kallmeyer (pants), Patou, Dior, Doen, La Veste, Jamie Haller (pants, denim, loafers), Loulou Studio, CO, Miu Miu, Loewe, Dries Van Noten, vintage and current Prada, vintage Chanel, DONNI, Flore Flore (tanks, tops), By Malene Birger, Tibi, Bode and Savas — my favorite custom suede jacket is by this glorious designer!
Favorite places to shop: Mytheresa, Net-A-Porter, The RealReal. Etsy like nobody’s business. Five One Five in Charlotte.
Favorite occasion to dress: I like when I get the opportunity to go the extra mile. I like getting dressed for dinner.
THE CLOSET
Your closet is the definition of minimalist chic. Can you elaborate on the design? When we purchased this house, I did some design work myself. During Covid, Emily Bourgeois redesigned my bathroom [and dressing area]. She is so good at what she does. The design suits this home. It really honors the house, and that’s what we wanted.
Favorite wardrobe item: A vintage leather motorcycle jacket I got in Provence. We went to this little market, and this woman had them laying on the sidewalk. It looks like it was a custom, real motorcycle jacket. It gives me all of the ’90s vibes.
Advice for creating an enjoyable dressing room: Make it work for you. It’s your private space, and it needs to function in a way that helps you get ready and out the door with the least amount of stress. I love all the showy closets — whatever makes you happy, that is fabulous — but I would constantly be worried about making a mess. You have to make a mess to get dressed. [Getting dressed is] a sport for me, and for a lot of people. SP
THIS OR THAT
Natural or synthetic: Natural fibers, always
Solids or patterns: Both
Long sleeves or second layer: I’ll do a long-sleeved oxford, but I’m a layerer.
Spring/summer or winter/fall: So hard, but I love spring/summer.
Heels or flats: Block heels
Wardrobe staple or statement piece: Statement piece, obviously
Sunglasses or purse: Sunglasses
Pop of color or monochrome: Depends on the day
Silver or gold: A mix
