A striped sweater like this merino-wool crewneck from Rag & Bone is the perfect complement to a simple woven shirt. It's also softer and more comfortable than typical Shetland-wool varieties. If cost is a consideration, J. Crew offers a strong alternative: Its extra-fine merino-wool knit V-neck is soft and layerable, and its slim fit will retain its shape after countless wears. [Watch by Bulova, $150]