Transitional Dressing with Lilly Sisto

For the past few years now, we’ve had the joy of teaming up with style icon, talented creative, and close friend Lilly Sisto—who has an iconic approach to dressing, mixing highs and lows. Together, we’ve created our second capsule designed to be worn effortlessly season after season, and seeing how so many of you have styled these pairs worldwide has been incredibly special to us.

As warmer days approach, and in the same spirit in which this capsule was created, we sat down with Lilly to talk about transition dressing: how she moves between seasons with ease, what she’s wearing now, and how these pieces continue to evolve with her wardrobe in the most stylish way.

1. As much as we look forward to each new season, we also believe in investing in pieces that carry through the year rather than being confined to a single moment. What pieces do you consider essential for making the transition feel effortless?
I’ve always believed in building a wardrobe around pieces that live beyond a single season and can evolve with you throughout the year. For me, shoes are one of those essentials. They’re so much more versatile than we give them credit for, and the right pair can completely change a look with just a few styling choices. I love that a great pair of shoes can move effortlessly from summer to fall simply by adding an additional layer, pairing with cute socks, or reimagining them in a new way.

2. When designing the capsule, did you think about how the shoes would be styled across seasons? If so, what choices reflect that versatility?
Yes! I’ve always loved ballet flats and Mary Janes because they’re beyond comfortable in every season and can make an outfit feel instantly polished without trying too hard. When designing this capsule, I wanted each pair to feel seasonless. In summer, they’re effortless on their own, and in winter, they pair beautifully with socks or tights for a cozier, layered look. Every color and silhouette was chosen with that year-round versatility in mind so each style feels timeless rather than trend-driven.

3. How are you styling these days? Can you share a few favorite looks that feel true to your personal style right now?
Lately, I’ve been leaning into simple, balanced dressing, starting with an easy base like a perfect white tee or vintage denim jeans and building from there. The New York weather keeps me on my toes, so I’m always thinking about layering pieces that can adapt throughout the day. It’s about finding that mix of comfort and polish that feels effortless but considered.

4. Socks, tights, maxi skirts, trenches—are you incorporating any of these items into your wardrobe right now? And if so, how do they work with our capsule?
All of the above! Each shoe in the capsule has its own personality, so they really come to life when styled with different layers and textures. I especially love pairing them with maxi skirts; even though the skirt drapes to the ankle, those little flashes of color and shape when you walk make the whole outfit feel dynamic. It’s those small details that make getting dressed feel exciting.

5. Are there any trends you’re particularly excited about? And how would you adapt them to your style?
I have been loving the return of classic tailoring this season - structured coats, school-girl skirts, and the resurgence of ballet-inspired silhouettes. I like taking those timeless elements and softening them with something unexpected, like a bold flat or colorful tights. It’s about creating contrast that feels refined but playful.

6. If you had to pick one style from the capsule to carry you from the summer to the winter, which would it be and why?
The Como Ballet Flat! The red is that perfect balance of bold and timeless. It adds a statement to a summer look, but transitions beautifully into the holidays. Winter tends to lean darker and more muted for me, and I love how the Como adds an instant lift and a little hit of brightness that feels joyful even in the colder months.

Discover the perfect transition styles here.