Theory Zaine Clifton Pants

A traditional plaid pattern adorns the collar, pocket trim and vents of this handsome shirt from Fred Perry.

The contrast crewneck sets the tone for this extra handsome sweater, softer than soft in plush merino wool and rife with casual polish.

Slide into these extra supportive penny loafers from Cole Haan for a full day and night of comfort and classic style. Featuring concealed Nike Air technology in the heel and a colorful suede upper, they give you their full support whether you're shuffling to work or just walking off a big dinner in Little Italy.

A reserved tie in pure silk says you mean business and complements your dress shirting for a look of classic distinction.