Loafers and moto boots are the transitional footwear choices Olivia Jade and Lila Moss are wearing now.
Shorts have become the defining piece for fashion-forward women in their twenties this season. From denim cutoffs to athletic micro styles, the silhouette dominates summer wardrobes for good reason—warm weather remains in full swing. Yet insiders are already demonstrating how shorts can extend well into autumn through strategic footwear choices.
Two flat-shoe styles are leading this transition: loafers and moto boots. Though traditionally associated with fall, both carry timeless appeal that has prompted style setters to adopt them early. Olivia Jade and Lila Moss exemplify this approach, each stepping out in New York City this week with distinct interpretations.
Jade assembled a relaxed yet refined outfit pairing blue drawstring shorts with a black T-shirt and black loafers. She accessorized with an oversized shoulder bag and low-ankle socks. Moss, meanwhile, combined distressed denim shorts with a low-scoop white tank top and mid-calf moto boots, finishing with a leather belt and shoulder bag.
Either direction offers a viable path for extending shorts into cooler months. Both footwear options lend bottoms a deliberate, editorial quality while introducing autumn sensibility without appearing prematurely seasonal.
Shopping the trends
The market currently offers numerous options across both categories. Standout loafers include Jamie Haller's comfort-focused designs, which editors frequently praise, alongside pairs reminiscent of The Row's coveted styles and others channeling Miu Miu's aesthetic. Vintage-appearing distressed leather and elegant colorways rank among desirable details.
For moto boots, shoppers note that certain styles sell out annually each fall. Classic, timeless pairs remain wardrobe staples that fashion insiders return to year after year.