1. Banana Republic Crimson Heritage Merino sweater, gingham-check woven shirt, slim-fit chino, chocolate leather belt, crimson and grey ribbed beanie, herringbone scarf, and Chelsea boot; $29.50–$168. Fairfield, 203-256-8244; bananarepublic.com
2. Bontrager eVent Packable Stormshell; $220. Trek Bicycle Store, Fairfield, 203-256-8735; trekfairfield.com
3. J. Crew Basket-weave belt; $75. Westport, 203-226-2739; jcrew.com
4. Margo Petitti 5 stripe scarf made from 100% Italian wool in various shades and patterns of blue, navy, purple and gray; $210. margopetitti.com
5. Hermès Sport Shoe in suede calfskin; $1,050. Available at hermes.com, select Hermès pieces available at Mitchells, Westport, 203-227-5165; mitchellsstores.com
6. Tumi Dror Messenger; $495. Innovation Luggage, Westport, 203-255-2337; innovationluggage.com
7. Deakin and Francis Cufflinks; call for pricing and availability. Kasson Jewelers of Southport, 203-319-0021; kassonjewelers.com
8. Chopard Mille Miglia GT XL Chrono Split Second Timepiece; call for pricing and availability. Manfredi Jewels, Greenwich, 203-622-1414; manfredijewels.com