Saddle shoes are seldom spotted in today's world, but I believe it is a plus to insert them into your shoe rotation. Now I admit, I would not wear them everyday, or every week for that matter. However, they are undoubtedly classics, and they fit within the Ivy League/WASP style. Their height of popularity was probably in the 50s, and they were common among professors and students at Ivy League schools. They are a casual shoe, and they come in different color combinations. The saddle shoes pictured above are navy and bone, and they would look great with a blue blazer, chinos, oxford button-down shirt, and repp tie. Saddle shoes with brown and bone/ivory or brown and brown suede look good with a tweed jacket and chinos. Also, consider the photo from the camel hair jacket post. Imagine the outfit displayed with gray flannel trousers and brown and ivory saddle shoes. Saddle shoes can also be worn with a casual suit (tweed, seersucker, chino).