Hello and welcome to Twisted Wonderland headcanons :) My name is Ciel / Circe
I'm still the admin of @twsthc, back and better than ever. Here I'll continue revising and posting my TWST headcanons, hopefully with better organization and graphics ^_^
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Riddle Rosehearts: I think her mother, like with most things in her life, controlled her wardrobe with an iron fist. Their outfits were to be "proper," with an exuberant amount of buttons and zippers that made their 5-year-old head spin. Most of her clothes were a solid beige, gray, black, or white. Grass stains were a death sentence. NRC- being the quirky school that it is- was her first exposure to colorful outfits with flamboyant patterns. Their unique dorm uniform gave them a taste of multicolored variant clothing, without breaking any rules. Soon enough she found her own style, but I do think she finds comfort in familiarity and sometimes dresses the way she has for the majority of her life.
I think they dress modestly. I've always seen Riddle as transfeminine, so I imagine her wardrobe is girly :3
Cater Diamond (freshman year): First of all, I think Cater is a fast fashion demon. I totally see her as someone who bugs you to download TEMU for referral codes. Sorry! Every year he shows up to class with a new distinct style. The clothes she gets tired of are donated to close friends or random underclassmen (yes, she's so generous and such a good senpai). His first year look is inspired by the freshmen characters introduced at the end of Mean Girls (2004).
Cater Diamond (sophomore year): I don't remember having a reason for him dressing this way his second year, except for "it looks cool and like something he'd wear."
Cater Diamond (current year): Apparently this style is called McBling, or Trashy Y2K or something. With all the bright pink and body glitter, it just screams Cater. Vintage but trendy, flashy, eye-catching... Cater. I don't think he fits the criteria of "mean girl," and he certainly wouldn't be a Plastic, but that doesn't stop him from serving Regina George or Elle Woods. I think this is the style she likes the most and would stick with the longest.
Ace Trappola: I based him off two of my friends, one an eccentric writer and one a broke skater. The writer shows up to class in shirts that say "I SURVIVED THE ABORTION" and "I ❤︎ MICROPLASTICS" in bold letters, and the skater has a collection of thrifted belt buckles. This style was surprisingly difficult to make a moodboard for. Sorry Ace.
Deuce Spade: All the clothes he bought during his delinquent phase still fit him, it would be silly (expensive, burdensome on his mother) to get a whole new wardrobe. Sure, the affliction tees and cross embroidered barrel pants don't match his NRC A+ persona, but it's not like he's gonna toss good clothes into a Goodwill bin.