Mark McNairy, $420
It's something women have known forever—a secret weapon in their sartorial arsenal. A pair of bold shoes (be it in color or in pattern) will instantly add some interest to your day-to-day kit. You notice the shoes first, of course, but then see the person wearing them in a whole new light. The always irreverent Mark McNairy is the master at these kind of shoes. Traditional, yes, but with a touch of technicolor sneakerhead swagger. Tommy Hilfiger just released a slew of Bass Weejuns in plaids and preppy colors like bottle green. Or Duckie Brown's take on pebbled leather brogues for Florsheim. The egg yolk yellow pair was made famous by a certain street style demigod, but the shoes also come in seven other Crayola colors. After all, what could be better for facing the gray days ahead?
Tommy Hilfiger, $198
(available at Tommy Hilfiger stores or by calling 212.223.1824)