Main Street: Elyse Winter

"...don’t ever google a place to get the vibe. Pick your own vibe."

May 13, 2025

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

Stylists know a lot. And a lot of what they know, no matter how useful, never makes it into our personal toolkits. Their knowledge can feel out of reach, or maybe too detailed. Something for someone else out there with a less busy, less messy life. But today, we’re giving ourselves some freedom to play around in this world because we have stylist Elyse Winter on Main Street!

What I love about Elyse is that she styles real women for their real lives. She has a clear perspective on style, which I can tell is the result of years of honing. She’s the reason I know how to style a button-down. And so much more.

Here she is…

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

Elyse: Where do I start, ha! I was born and raised in Los Angeles and lived in NYC for 6 years with my husband. We’re now back in LA because of support and family and have a little girl named Gemma who is 2 1/2. We are expecting our second child this fall which is wild and exciting.

I’ve always loved fashion and interned for everyone under the sun when I was getting started in my career. I went to fashion school in LA and then later worked for Nordstrom, Barney’s, & Farfetch as a stylist. Throughout my years in the industry I picked up personal clients that followed me and have trusted me for years. After I had my daughter I knew I wanted to fully commit to styling and starting my own business full-time. Since then, I have grown my business into something I couldn’t have dreamed of. I have over 200 clients all over the U.S. and in the U.K. and get to work with the most amazing brands I’ve looked up to forever. A lot of sacrifice and hard work has lead me to this and I’m so excited for the future.

Throughout the week I’m meeting with new clients to do clean-out sessions, working with existing clients to style them and fill in their closets, & partnering with brands to highlight product I believe in. This month I’m fully grinding and laying the foundation for what’s to come before baby number 2 comes. Next month I’m hosting an event in LA and then I’m headed to NYC with Bottega and I’m beyond excited for that trip.

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

Elyse: I have a few principals I live by and share with my clients.

One is to fully enjoy everything I own. It’s silly to set things aside because they’re too precious or special. I wear white jeans with my toddler & my diamonds with a tshirt (not a gown).
Another is to lean in to how I want to feel and look vs focusing on what others think about me. One day I want to be boho LA mom in an Elder Statesman sweater, the next I’m craving structure and simplicity in a Blaze Milano blazer and Jeans. I never set out an outfit for the next day for this reason… you never know how you will feel.

Left: Elder statesman sweater with vintage charms Right: Vintage sweatshirt with Sherman Field necklaces.

Lastly, I focus on jewelry as a major way to show my personality and style. I’m very casual and can be caught wearing sweats like any normal mother. In order to make that feel more “me” I add a ton of jewelry.

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

Elyse:

Vintage Levi’s
Sherman field necklace and locket
Manolo Carolyne black suede 50
70s converse in cream
White tshirts from Flore Flore
Commesi button downs
France’s de Lourdes Johnny tee for date night
Skims cotton boyshort / scoop bralette

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

Elyse: Start with the basics. I generally start my outfit with a crewneck white tee and jeans. Build your outfits from there based on your mood. Don’t ever ask your friends what they’re wearing/don’t ever google a place to get the vibe. Pick your own vibe.

Olivia: Who do you look to for inspiration?

Elyse: Oh boy, such a long list. Top of mind, I get a lot of inspiration from my friends and designers I look up to. I especially love French street style and am so inspired by the casual and effortless way they go about styling pieces. I’m always scrolling online to see new products that are delivering, vintage pieces I see from my friends Ness at NUNU vintage, & honestly my clients. Whenever I leave a closet clean-out I usually end up buying at least one piece they have. They just don’t know it!

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?

Elyse: All I want is to go to Paris for a few months with my mom. I would be wearing exactly what I love now- for night I would wear vintage black Levi’s, a Flore Flore white tee and a row blazer over the shoulder with a kitten heel for dinner. For day I would wear vintage blue Levi’s, that same Flore Flore white tee, a vintage Kelly bag and 70s converse. Ugh I love Paris.