Rosie Assoulin Top & Pants, Delvaux Bag, Sebastian Milano Heels, Arielle Ratner Earrings

There’s something about checks that just feels like spring. They’re one of those patterns that returns year after year and still feels fresh every time. Gingham sits within that family as the lighter, more playful option, while other check variations feel a bit bolder and more expressive.

A fuller skirt or midi dress feels right for daytime celebrations like showers, luncheons, or anything outdoors where you want to lean into the spirit of the season. Matching sets have a slightly more styled feel, perfect for dinners, casual events, or when you’re rushing out the door.

Part of what makes checks endure is the way they continue to evolve. They appear in everything from classic, ladylike silhouettes to pared-back, modern shapes, shifting with each era while still holding onto their signature simplicity. That versatility is what keeps them feeling relevant: familiar, but never static.

The month of May always tends to feel like a final sprint. The kids are counting down the days until summer break, and the calendar is suddenly booked out for weeks. I’ll admit the pace can feel a little frantic, but it’s also one of my favorite stretches of the year. Charleston is in full bloom, the evenings are getting longer, and there’s an eagerness for the shift in energy ahead.

So much of this month is built around things that have been in motion for a long time: the Mexico trip we planned last year, our formal living room we started designing with Summer last spring, a new collaboration we’re finally kicking off. Here’s what’s on my radar for May.

What We’re Doing

• The last month of school! The kids are counting down the days, and we’re in a panic to fit in as much as possible before they’re home all day! 
• We’re heading to our interior designer Summer Thorton’s home in Mexico! We’ve been planning this since last year and cannot wait!
• Some of my favorite fine jewelry designers have been coming to Charleston! I had a visit from Danielle from Sherman Field to shoot a feature with her and got to preview her newest collection (it’s very colorful and very me), I had the pleasure of co-hosting a pop-up with Retrouvai (a brand I’ve long loved and have a few pieces) last week alongside with brand HighSport, and finally got to meet Irene Neuwirth at an event she had at The Dewberry last week– another brand I had long-loved and have probably the most pieces from than any other designer. Jewelry is so personal and with fine jewelry, it’s so wonderful to get to touch and try on. Because of the price point, many of these pieces I’ll sit with and think about for months (or years) before making a decision. For example, my Sherman Field locket (sold-out, similar here), which is probably my most-worn piece, was a long, waited purchase. 
• I’m kicking off the design process this month for a collaboration that will launch spring of 2027. It’s a brand you all love– and it’s one that is such a great fit and I’m beyond thrilled about! We have two more launching this year, too!
• I am excited to dig into Beneath this month after reading Conform in January, along with Yesteryear (recommended by a close friend)
• Thomas’s birthday is at the end of May, so I’m already trying to brainstorm gifts for him– he’s a hard shopper (he only likes really practical things)
• Our formal living room is being installed at the end of the month! We designed this room with Summer last spring and it’s finally *almost* ready. The room has been under construction for the past month and I can’t wait to see it come together. 

What I’m Wearing

What I’m Buying

What I’m Eyeing

I recently attended an evening with Oscar de la Renta celebrating Save Venice, a nonprofit dedicated to preserving and restoring Venice’s artistic and architectural heritage. The organization funds conservation projects throughout the city, helping protect its cultural legacy for future generations. It made the night feel both beautiful and meaningful.

It’s the kind of evening that signals a shift in the season when invitations pick up, the pace quickens, and dressing takes on a more celebratory rhythm. It becomes about presence, selecting pieces that feel intentional, elevated, and distinctly formal. Whether it’s a gala, a spring wedding, or an evening that calls for something with impact, the focus turns to silhouettes and fabrication that feel impeccably executed and visually striking.

This edit leans into luminous satins, intricate embellishments, sculptural draping, and soft, romantic color such as pale yellows, washed pastels, airy florals, and the occasional saturated tone for contrast. A balance of fluidity and structure runs throughout, with column gowns, strapless shapes, halter necklines, and controlled volume that moves with ease while maintaining shape. Pieces that hold their own in a room and remain just as compelling the next time an invitation comes around.