I think everyone has a different personal perception of the Cole Haan brand, but I would describe it as a cross between classic and almost vintage American fashion, and sporty and contemporary.
The logo says a lot about the brand.
The sewing needle and string in particular, are a sign that tailoring and traditional hand-made craftsmanship is something the company would like to be attributed with.But the fresh color palette and the simplistic and modern flat design of the logo suggests a more up-to-date and modern aspiration.
The Cole Haan shoes I've seen reflect this theme to a tee.
Classic style, but with quirky detail (such as the brightly colored soles:
And the Cole Haan advertising campaigns represent the same two concepts:Classic-
But modern and sporty -