On Jackie's first day in the Residence, she asked Bernard West, the chief usher in the White House to take her so she could meet all of the cooks, maids, ushers, etc. Jackie liked to wear sports wear in her casual wardrobe. When the staff came to meet her, they were shocked to find her in a pair of jodhpurs and a white shirt.
Jackie's casual wardrobe was usually seen around the White House. Her year would later fan out into weekends at Glen Ora and Wexford, there would be short trips to New York, to watch ballet and trips to the theatre plus a bit of shopping and some browsing at art galleries. Then there was Hyannis Port for the summer and Newport in September.
One example of Jackie's love for being casual was at Caroline's 5th birthday. It was celebrated with a party in the family dining room in November 1962. Jackie wore a simple burnt orange silk sheath as she carried in the cake to her beloved daughter. Then when members of a Native American council came to call on the President, Jackie invited them to visit John-John in the residence. She wore a simple pink wool dress with a plaited skirt.
After JFK's death, Jackie did continue to dress fancy but turned back to her casual looks.