Trey says that “every last detail” of Riddle’s lift had been predetermined for him prior to NRC, including what he wore, so it is possible that he is still learning what it is like to have the freedom to wear close of his own choosing.
When asked how he dresses in casual settings Riddle explains, “I generally prefer a smart, casual look, and avoid dressing non-formally. My parents told me never to leave the house without a tie,” and he has recently learned that his “casual setting” attire isn’t the “catch-all” that he wished it was.
Riddle explains, “There was a time when I joined a group of four going shopping for Equestrian Club supplies in town. When I arrived at the meetup spot, the others looked at me strangely. ‘Are you really going dressed like that?’ they asked. The supplies we needed were heavy, so I wore my PE uniform expecting to do some heavy lifting. I should have dressed casually. But I didn’t have a single non-formal article of clothing suited for heavy exercise.”
To rectify this oversight, Riddle says that he conferred with Cater and Ace, who are more familiar with fashion: “They said my wardrobe was too formal, and I’d stick out from the rest of my clubmates like a sore thumb. There’s no telling when I’ll be able to go on another outing with other students. It would be a breach of etiquette to make the rest of the group uncomfortable, so I deemed it necessary to remedy the issue at once.”
Cater and Ace suggested that he dress down the clothes he currently owns by wearing a shirt with no tie or leaving a top button undone, but he “just didn’t feel right without (his) collar properly buttoned.”
In compromise, Riddle explains, “we settled on dressing down by going with different fabrics and sizes…I also went out into town with them to get their help in picking out a few clothing items. If I have occasion to go out with school friends again, I’ll wear what I bought then.”
Riddle has a voice line of, “I make it a rule to iron my shirt every morning” and, “Are my tie and collar in order? A uniform must be worn properly.” In Book 2 he straightens the prefect’s tie.
Riddle wears high heels with his dorm uniform because they are “modeled after the Queen’s. I’ll have you know. To be clear, that is the ONLY reason the heels are so high,” and in a vignette he tells Jack, “It takes work to look good walking in heels.”
In another vignette we learn that Riddle struggled when he first started wearing heels in his first year at NRC, once accepting a bandage from Vil after getting a blister.
Riddle tells Vil, “The night you gave me the bandage, I ordered a manual on proper walking technique. I also watched videos on correct posture and how to adjust your center of gravity to walk more gracefully, and added both to my training regimen. l’ve also learned that heels offer unique benefits other footwear doesn’t. When I make an effort to walk elegantly in heels, I elevate my line of sight, and my back and neck straighten out. I also enjoy how good posture makes me feel more energized.”
When Vil says “High heels make us look stronger and more attractive,” Riddle agrees: Not to mention, It’s pretty gratifying to watch the Heartslabyul students instantly straighten up when they hear my footsteps. That kind of clarion clacking only comes with a good pair of heels…A single footstep can announce one’s presence, while inspiring both respect and fear. Given that we represent the dorms honoring those queens, our shoes should be no less sharp.”
Riddle’s gym uniform is oversized because he “bought a slightly larger gym uniform assuming that (he) would grow taller,” but it has not happened. This is possibly meant to tie into his mother’s strict calorie counting from when he was a child, which Riddle seems to still be adhering to at NRC.
In Trey’s dream of Book 7 where he has been free to eat “whatever he likes and has as much of it as he wants,” the dream-Cater says that Riddle “even traded in that baggy PE wear for a bigger size three times in one year.”
Riddle does not like being reminded of his small stature, compromising his group’s plan to deceive Eliza and save Idia during the Ghost Marriage event when a ghost guard tells him that he is too short to be considered. Riddle says. “They say that, in general, men continue to grow until they reach 18! I still have a whole year!,” and Ace responds, “Sounds like you looked up that factoid yourself. Has this been bothering you?” But Riddle claims, “Not at all! What bothers me is people who judge others by their appearance!” (Riddle: “It’s what’s on the inside that matters most.”)
Riddle says that he has had the same hairstyle since he was a child, and he was cutting his own hair to keep it short when he first came to NRC. As “Cater didn’t want (him) doing it for some reason…” he now goes “to a barber in town, just like everyone else.” (Jamil :”You should probably thank Cater for that.”)
Riddle again cuts his own hair at the conclusion of the Lantern event, with Jack exclaiming, “There’s such a thing as being too bold! Even I can tell that straight cut looks wrong on you!” Deuce follows with, “We’d better scrounge up some scissors before we get back to the dorm. I’ll clean it up for you. I can’t let my boss be seen looking improper. I gotta uphold our dorm’s rep!,” surprising Riddle (“Is it that bad?!”).
Twisted Wonderland Reference Note 