Exploring Megan Draper’s Style in 2025

As we ponder the age-old question of what Megan Draper would wear in 2025, Simon Miller’s fall collection may hold the answer. Chelsea Hansford, the creative mind behind the brand, has taken inspiration from the iconic conversation pit of the midcentury era to create a collection that is both nostalgic and forward-thinking.

This season, Hansford has infused a 1970s sensibility into her designs, with striped, earth-toned knitwear and wooden clogs making a statement on the runway. The signature tie-back Loch Top and fringed Za Za skirt have made a comeback, this time in new colorways and fabrications that push the boundaries of traditional Simon Miller pieces.

One of the standout elements of the collection is the introduction of occasionwear in brocade and teardrop sequins, adding a touch of glamour to the otherwise laid-back aesthetic. The colorblocked knitwear also caught the eye, showcasing Hansford’s willingness to take risks and experiment with new silhouettes.

With Simon Miller’s recent growth, including the opening of a brick-and-mortar store in downtown Los Angeles, Hansford has found the confidence to expand her design repertoire and cater to an evolving customer base. She notes that as the brand matures, so too does its audience, allowing for more creative freedom and exploration.

“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,” Hansford explains. “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.”

With Megan Draper’s timeless style as a guiding force, Simon Miller’s fall 2025 collection offers a fresh perspective on retro-inspired fashion, blending the past with the present in a way that feels both familiar and exciting.