To Boot New York Men's Hayden Loafer

Fossil's functional, waxed canvas Estate Messenger has it all – a vintage-inspired design, a padded laptop compartment, and enough interior pockets to keep all of your daily must-haves organized.

Leather Upper

Leather Sole with Rubber Inset

1" Heel

Lace Up Dress Oxfords

Nautica uses a subtle stripe, a reversible knit, and its streamlined spinnaker logo to turn the classic sailor's cap into this season's most versatile headgear.

A good winter scarf is a must-have for every man, and this one from American Rag is a classy choice.