Street View is a series in which Isa Giallorenzo spotlights fascinatingly fashionable Chicagoans.

Ashanti is wearing casual items, but she polishes them up by carrying a structured bag, pulling up the neck of her denim jacket, and by tucking her Cosby sweater in—”tucking in” is a great outfit polisher. A pompadour hairstyle also glams up any look.