This old-fashioned mall (known to most simply as Montgomery Mall) has enough department stores and boutiques that you and your mother are guaranteed to find your size (32/30) and style (Dockers, greenish-khaki, flat front, Mom!). It is far enough away and not even close to being Metro-accessible, so you can rest easy—your hipster friends will never spot you and your mom scouting for pants. If you’re lucky, your mom may splurge and take you to California Pizza Kitchen. If you’re nice, your mom may even take your greenish khakis to the in-mall tailor to have them hemmed while you eat.

—Jason Cherkis