Aspects herein provide for an apparel item (100) for upright sleeping. The apparel item (100) comprises features to reduce distractions such as a hood (124) with an integrated eye mask (310) and foam inserts (314) integrated into the hood (124) and configured to be positioned over the wearer's ears when the hood (124) is worn. The apparel item (100) further comprises a strap system (400) that is configured to hold the wearer's head in a static position during upright sleeping.