Coastal Grandmother To dress like a coastal grandmother, start with easy-going white button-downs or breezy tiered sundresses in the summer. In the fall, swap them for beige knit sweaters and pants, and finish with a bucket hat and tote bag. The coastal-grandmother aesthetic is all about those lightweight staples that conjure up images of lounging poolside or drinking a glass of wine in the garden. Image Source: Getty / Jeremy Moeller