1. A varsity sweater has the polish of a blazer, but it's far more relaxed.
2. Upgrade your tee to a chambray shirt.
3. Saddlebags outclass messenger bags but still leave your hands free.
4. A skinny riding pant offers more structure than leggings.
5. A compromise between stilettos and flip-flops: the stacked-heel boot.
Blazer, Autumn Cashmere, $395 at Skirt, Bryn Mawr, Pennsylvania; 610-520-0222; Shirt, $178, 7forall mankind.com; Bag, Dooney & Bourke, $350; dooney.com; Pants, J Brand, $227, Saks Fifth Avenue; 877-612-7257; Boots, Stuart Weitzman, $695; 212-750-2555