Dressed Down

Break up your suit by replacing the blazer and dress shoes with a jacket and sneakers. No one has to know you planned your rogueish look so meticulously. Braided leather jacket ($6,100) and cotton-wool blend pants ($750) by Louis Vuitton; cotton T-shirt by Calvin Klein ($40 for pack of two); cotton socks ($10) by COS; calfskin sneakers ($1,300) by Dior Homme; Rebel Spirit watch ($265) by Thomas Sabo.