Old Pasadena is the rare California shopping district designed to be walked in summer. The buildings along Colorado Boulevard between Pasadena Avenue and DeLacey are mostly late-19th-century brick and stone, two and three stories, with a near-continuous run of recessed entries and canvas awnings. The setbacks weren’t designed for shade specifically — they were designed for window display — but the result is that a north-side walk on Colorado at noon stays under cover for about 70% of its length, broken only at the cross streets.
The other piece of the system is the alley network. Old Pasadena has three named alleys running parallel to Colorado — Mercantile Place, Union Street, and the unnamed delivery alley behind the south-side block — that hold deep building shadow through most of the afternoon. The alleys are narrow enough that the second-story walls do almost all the work. The picks below mix the boulevard and the alleys; the trick is to use the boulevard for the storefronts you actually want and the alleys for the long connecting walks.