Masha Ossovskaya: On the Rocks

LA-based stylist Masha Ossovskaya has style all her own. A dash rebellious rocker while still honoring the classics, all in good fun. We love how she wears jewelry because whether new, vintage, or family heirloom, she makes it her own and it hooks you in.

Masha entered the world of celebrity styling through assisting some of the top names in the industry, including Cher Coulter, Petra Flannery, Erin Walsh, and Sally Lyndley. Now on her own, she’s always up to a mix of luxe endeavors. Masha has worked with the likes of Eva Mendes, Nathalie Emmanuel, and Lucy Boynton, plus she’s a contributing editor to SBJCT Journal. One busy lady!

In between appointments, we met up with Masha at Cafe Stella over lattes and avocado toast (so LA!) to learn more about the grind of life as a stylist and the role jewelry plays in her work and life. -Jenna Wise for The Stone Set

Tell us about yourself. What’s your day-to-day like as a stylist?
I am an LA-based fashion stylist. I was born in Russia and moved to California with my family when I was 8. I always knew I wanted to work in fashion, but I actually fell into styling by chance. When I moved to LA after college I was working at a fashion PR agency and met a stylist who was looking for extra help. She asked me to come to a shoot one day and that’s when it clicked that this was what I wanted to do.

I haven’t looked back since. Honestly, no day is ever the same, which is part of the reason that I love this job. I could be calling in looks for fittings, getting clients ready for events, collaborating with photographers on concepts for upcoming shoots or hitting the stores for my personal shopping clients.


You’ve worked with amazing women like Cher Coulter, Sally Lyndley, Petra Flannery, and Erin Walsh. What did you learn from them?
I have been really lucky to work with such incredible women. They each have such a unique style and point of view. Working with Petra was my first introduction to celebrity styling and I would say I learned everything I know about this job from her. I started working with her on the weekend of Oscars, which if you ask any stylist is probably the craziest weekend of the year.

I hit the ground running, and would not be where I am today if it wasn’t for her. I think what they have all taught me is the importance of listening to each individual client and their needs and how to fuse their style with yours to make them look like the most beautiful version of themselves.


What have been your favorite career highlights to date?
Working on Alessandro Michele’s first Gucci campaign.

How do you describe your personal style?
Minimal modern with a touch of rock and roll. My outfit generally depends on how I’m feeling that day and what I have to do. There is no typical.

What jewelry are you drawn to? Who are your favorite designers?
There are so many amazing options out there but I would say my favorite are statement pieces…I live for a big earring. I love Mounser, Charlotte Chesnais, Spinelli Kilcollin, Cartier. Beladora in LA has the most insane vintage collection.


What are you wearing? Why are the pieces special to you?
I’m wearing Sarah Chloe gold hoops that were designed by the lovely Elle Strauss. The huggies and studs are pretty much my everyday staples; they are Catbird and Jacquie Aiche. I love multiple ear piercings. I think I add one on every time I go to one of Jacquie’s parties.

The snake pinky ring is also Jacquie Aiche. It was a birthday gift from my parents. The cameo ring I got in an antique store in Italy last summer when I was on vacation with my mom. The “oui” ring is a nod to my obsession with the French and it is stacked with tiny diamond bands from EF Collection and Jennifer Meyer, both gifts from the designers.

The black onyx ring is my great grandmother’s. It was given to her by my great grandfather and is one of my favorite pieces. The signet pinky ring is by Luna Skye and was one of the first pieces of jewelry I bought for myself.


What are your must-haves right now? Styling tips, please!
Very into kitten heel, strappy, 90s sandals. A small, structured bag…my personal favorite is the By Far Mini Bag in red embossed croc. Oversized blazer, I love wearing it belted. Beige…whether it’s a tonal suit, a high waisted trouser worn with a white tank or a beautiful silky slip you can’t go wrong. A cool pearl earring. Mounser makes a mismatched pair that is my fave.

Describe a dream day.
Any dream day for me starts with a workout, usually at Prevail, my go-to boxing gym. Followed by a yummy brunch with friends, a trip to the beach (there is a secret spot in Malibu that is my fave) and spicy margaritas and dancing to end the night!

Photography by Emerald Carroll for The Stone Set