A question we’re all often asking ourselves: What would Megan Draper wear in 2025? With Simon Miller’s fall 2025 collection, Chelsea Hansford may have an answer.

This season, rather than take inspiration from various far-flung destinations, Hansford based her entire offering around the conversation pit—the bygone midcentury design fixture that was just as cool as it was dangerous. (It’s a miracle Don Draper never took a spill in his after one too many Old Fashioneds.) “I was really drawn by the idea of this intimate human connection whether that’s lounging and reading a book, or listening to records, or dancing with your friends or sharing martinis,” Hansford said.

Hansford infused a 1970s sensibility into fall 2025, from the striped, earth-toned knitwear to the wooden clogs. Otherwise, Simon Miller hero pieces were still in heavy rotation: the brand’s signature tie-back Loch Top returned in a rusty satin and a brown and black striped colorway, as did the fringed Za Za skirt in a deep burgundy.

But, while the staples were there, it felt like Hansford was taking risks, introducing new fabrications and silhouettes, like occasionwear fashioned in brocade and teardrop sequins. The colorblocked knitwear was a particular highlight. Hansford’s broader approach stems from Simon Miller’s growth (the first-ever brick-and-mortar store recently opened in downtown Los Angeles), as well as her customers’ natural evolution.

“When the business grows, I think we can start to justify bigger swings. Now we have more flexibility to expand, and also more confidence in testing new things,” she said. “And I think our customer is maturing with us. We’ve been doing this for a bit, so it’s nice to see her growing up.”