I understand that Winnetka has two downtowns (Highland Park too, or three if you count Braeside). Hubbard Woods is somewhat small but it's well laid out and oriented around a beautiful town square at the train station. Green Bay Rd is lined with many unique and successful businesses and the street has great architectural character with mostly 1920s Tudor and Neoclassical.
From my perspective, Hubbard Woods is more beautiful than downtown Lake Forest, which is a weird eclectic architecture and purposefully auto-oriented, whatever that meant in the 20s. For the most part, though, the North Shore is pretty good urbanistically.
Glencoe's downtown is not even worth considering for the business mix, architecture, or pedestrianism. Lake Bluff and Ravinia do much more with less. It's often difficult on the North Shore to decide whether each downtown feels nice because of good design and planning, or because really wealthy people poured money into them to avoid embarassment.
I'm confident at least that Hubbard Woods is successful by design. It's a compelling place to be, which would remain true even if Ann Sacks and the Gap were replaced by pawn shops and bail bondsmen.
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la forme d'une ville change plus vite, hélas! que le coeur d'un mortel...
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