1. Burberry Prorsum Indigo Linen Jacket, $1,445 at MatchesFashion.com
2. Rag & Bone Blade III Black Herringbone Pants, $275 at Rag-Bone.com
3. Brera Eterno Solotempo, $800 at Barneys.com
4. Balenciaga Arena Trainers, $545 at Balenciaga.com
5. BOSS Black "Enzo" Solid Broadcloth Dress Shirt, $95 at Bloomingdales.com
Soundtrack of the Day: Machine Says Yes by FC Kahuna, $15.98 at Amazon.com