Growing up as an orphan in the bustling metropolis Honey Dew City, Hailie learned that survival by any means neccessary was the point of existence. Her gifted mind and amazing luck made her a legend in the gambling dens that were strewn across the city and with these skills she began to con people out of their money and make a name for herself as a con artist. Then the Drill Jaw Pirates attacked Honey Dew. When the Dice Pirates arrived, consisting of Dice, Kifer and Brigade, she became infatuated with Dice's happy go lucky attitude.
As a contrast to most of the crew, Hailie is one of the most normally dressed members of the crew. Her long blonde hair is held back in a ponytail and she wears glasses over her pale blue eyes. Her most common attire is a dark blue button down shirt, with the top buttons undone to reveal some of her cleavage, a short white skirt and golden high heeled shoes. Her physical attractiveness has been noted by many outside sources and even some of the crew, as Sly states under his breath how he love to do "This and that" with her. Her beauty has even saved the crew on one occasion, because the Marine Captain refused to attack their ship because of how beautiful he thought Hailie was.
After the timeskip, she has stopped wearing her glasses and lets her hair flow down to her buttocks. Her dark blue shirt has changed to a black tube top that reveals most of her middrift and her white skirt has changed to tight formfitting jeans. Her high heeled shoes have also been ditched for actual sneakers. Her physical maturation hasn't gone unnoticed, as when Sly sees her for the first time in 2 years he suffers a massive nosebleed and passes out. Her breast sizes have grown, and she has gained a slighly more curvacious figure.