Main Street // Meg O'Neill

"You move through your day and no one is wearing what you’re wearing, and that feeling of wearing something rare and special gives me a charge."

Jul 24, 2025

Welcome back to Main Street, the place to bump into perspectives on style from Land of Oaks and Roses readers and friends.

One of my closest friends, Lauren, has been telling me for years that I need to interview a girl she met at work named Meg. “She’s so thoughtful, so creative, has incredible style,” she would say.

Meet Meg! Also, this background print is by Alemais.

Well, today is the day! And now I know for myself that all those things about Meg O’Neill are true. What I love about this interview is that Meg’s not trying to tell you how to dress like her. Instead, she shares what it feels like to get dressed in a way that’s rooted in your own feelings, desires and sense of comfort. There’s so much to take away from this one!

Here she is…

Olivia: Tell us about you and what your life looks like right now.

Meg: I’m feeling pretty great because it’s summer and blazingly hot, and I wait all year for this to really come alive. It’s a combination of the sun—it just feels sooo life affirming and fantastic on my skin—and the kind of clothing that airless, languor-inducing, city heat mandates. I’m newly working for myself—I’m running a beautiful little sustainable shoe company called NAYLA; my first designs are launching this August and fall. We make shoes using fishing-industry waste, so by turning it into fish leather. It’s a gorgeous texture, and the colors are vibrant. I'm also launching a podcast later this summer called The Soft Life, which is about making life feel more abundant and rich by prioritizing the things that fill you up, like family, friends, developing your personal style, love, food, sex, etc. I’m super enjoying doing things on more my own schedule and the flexibility that gives me to parent and be around more for early camp pickup, hustling to mid-town swim lessons, or stopping on the way home to run through the sprinklers at the splash playgrounds. Alongside the uncertainty, self-doubt, and sometimes straight-up dread of running a business and being a parent, life is really so beautiful right now.

Olivia: What’s your perspective on getting dressed in this era of your life?

Meg: It’s got to feel like me, and it’s got to be comfortable and easy and not precious enough to allow me to dash to pickup, haul a stroller up the subway stairs when the elevator down there is undoubtedly on the fritz, and sweat—god do I perspire with all the running around I do. I’m always loving swishy vintage skirts and tiny halter tops, it feels so good and sort of outfit-making to have my back exposed.

I’m into big, loud and tropical patterned linen shorts lately (Alemais and Farm Rio rule). And whatever combination of those things I’m wearing, I’m throwing on a pair of my fish skin sandals. I’m a native New Yorker and I walk about a million miles a day, so I live in flat shoes. (I’m also the biggest Teva fan on the planet.) My hair is always in cornrows lately. They last for like 6 weeks, as in that’s 6 whole freakin’ weeks that I wake up and don’t do a thing to my hair! What a gift!! I have no energy for tackling my hair in the morning these days, and braids feel sleek yet beachy, sophisticated, and fun. They are perfection.

Olivia: What pieces are you wearing over and over again that we should know about?

Meg: I love vintage. It feels even more fantastic right now in this age of fast fashion and waste and intense planet degradation. You move through your day and no one is wearing what you’re wearing, and that feeling of wearing something rare and special gives me a charge. At the beginning of summer, I went to my favorite vintage boutique, Nomad Vintage in the East Village, and cleaned up. I bagged a Dries Van Noten dress that’s as delicate as butterfly wings (it’s totally see through, and I wear it with a big pair of granny panty briefs from Only Hearts); a Commes des Garcones creation that’s animal print and loose in the sexiest way that I recently wore for to messy picnic with my kids and mom and brother at the Botanical Garden; and a thong-ish bikini from the 80s, ha! I don’t always lunge for designer stuff, those just happened to be in my haul this time. Best store ever.

Olivia: Any advice for someone struggling to figure out what to wear?

Meg: You’ve got to feel like yourself. And that can change from day to day.

I’m an emotional dresser. Sometimes I want to look like I’m from the 90s and wear a cool baggy shirt that goes past my pants’ waste line. Sometimes I want to look (and feel) a bit masculine in camo pants. Other days I need to wear that butterfly wing Dries dress and feel like the most delicate flower. I think it’s about staying true to yourself, not just wearing what’s comfortable for you but also dressing to your mood.

Olivia: Who do you look to for inspiration?

Meg: Pharrell (his mashup of styles and genres and high and low gives me chills it’s so good), Jodie Turner Smith (chicest, coolest and love how her clothes showcase her gorgeous strong body), Gwen Stefani (love how she’s changed her style 1 million times with a throughline of just looking fun), young skater-y Anthony Kiedis (hottest but also want to be him), Diana Ross in the 70s (I mean, the glamor).

Olivia: Let’s dream a little… Imagine the thing in your life you’ve been hoping for came true. What would you be wearing as this next version of yourself?

Meg: There’s a Prada skirt I saw in a spread a thousand years ago that practically stopped my heart. It was A-line, fluttery, and the bright colors made me happy. I’m wearing that skirt, or something similarly incredible and Prada, and a pair of my (launching-in-August!) pale seafoam NAYLA mules. Dream!

For more from Meg, follow along with her here, explore NAYLA or listen to her new podcast here (+ just spotted a new Substack here!)