Compare an 1880s cycling cap (the style of the ones we wear, and in the ladies' sports fashion plate above) with an 1860s military kepi: Baseball caps were also influenced by these military styles (image below, left.) In boating circles they became ladies' yachting caps, as seen in this fashion plate from In boating circles they became ladies' yachting caps, as seen in this fashion plate from The Ladies' Home Journal , August, 1891 (below, right)
Dress sneakers are also seasonally adaptable
Thick wool or synthetic insulation works best for freezing temps, while lighter materials suffice for milder winters
Alice + Olivia ankle boots ($202)
The puffball mini silhouette is having its moment, and this woven version brings the architectural edge - structured enough to feel intentional, fun enough to wear without overthinking it