Summary:
・Riddle owns nothing less formal than “smart casual”
・Riddle has been told by his parents to never be without a necktie
・Riddle is uncomfortable wearing clothes casually (re: leaving the collar of his shirt unbuttoned)
・Riddle went shopping for clothes of the formality he is accustomed to in more casual fabrics, together with Ace and Cater
Riddle has a conversation with Rook about his outside-of-NRC clothing in his platinum vignette, where he explains that he does not own anything less formal than “smart casual” as his parents have told him that he is never to be without a necktie.
When meeting up with Equestrian Club members for a visit to Foothill Town to purchase club equipment he surprised everyone by dressing in his gym uniform, as he simply did not own any other easy-to-move-in clothing.
Not wanting to make others uncomfortable with his fashion choices, Riddle explains that he went to Cater and Ace for assistance, who recommended that he try dressing down his existing wardrobe by going without a necktie and leaving a top button undone on his shirts.
Riddle explains, however, that he felt uneasy about going without a properly fastened collar. Instead of wearing his existing clothes in a more casual manner, Riddle went with them into town to purchase clothing to his tastes in more casual fabric (Rook gives the examples of linen and sweat fabric) and with a more casual fit.
As of the platinum vignette conversation it seems that Riddle has yet to wear his new clothes, but he intends to do so at the next opportunity.
When a dream-version of Riddle becomes concerned about being dressed inappropriately, he goes to Cater for reassurance.
Riddle has a voices line complimenting the elaborate embroidery of his masquerade outfit, and may have an eye for quality. He describes his belly shirt of the Stitch event as “an appalling way to wear a shirt,” so such a style is possibly not a part of his usual wardrobe.
Riddle says he has had the same hairstyle since he was a child.
He also says that he keeps his hair short and would cut his hair himself when he first enrolled at NRC, but Cater did not want him to (“for some reason”) so now he goes to a barber in town (Jamil: “You should probably thank Cater for that”).
We get an example of Riddle cutting his own hair during the Rapunzel event when he does so with magic and is confused when Jack and Deuce react with surprise, with Jack saying, “Even I can tell that straight cut looks wrong on you!,” and Deuce insisting on fixing Riddle’s hair himself before they return to the dorm.
Twisted Wonderland Reference Note 