A system is provided to secure a pair of glasses to a hat, the system including a hatband insert configured to be inserted in a hatband of a hat, one or more hatband magnetic members configured to be selectively attachable to a plurality of locations of the hatband insert, and one or more glasses magnetic members configured to be attached to each temple of a pair of glasses, wherein the one or more hatband magnetic members and the one or more glasses magnetic members are configured to be magnetically attached to selectively secure the glasses to the hat.