For the Men

Jim Pak, entrepreneur and Washingtonian Best-Dressed 2009 

im’s Advice:
“I like to wear my boat shoes through the fall but in a richer color or suede—it brings a little casualness to a jacket-and-pant outfit that can be worn day or night. One can also wear cotton or silk light-weight sweaters through the fall.”

How we worked it:
Somber navys, grays, and burgundy get a little smart aleck with the help of intensely kelly-green top-siders. A gingham button-down—a summer staple of prepsters everywhere—goes urban with the sleeves rolled up and layered under a slim-cut grandpa cardigan, and classic fit cords and a sporty nylon parka keep the whole thing young and casual. With so many pieces on top, a brown tank watch is the only accessory you’ll need.

Billabong Twitter Cardigan, $54.50.
Paul Smith Cotton Gingham Dress Shirt, $148.50
Ralph Lauren Telford Boat Shoe , $209.53.
Homo Emerito Navy Parka, $99.90.
O’Neill Vagabond Cord Pant, $49.50.
Nautica Chronograph Watch, $175.