I really like how Tangled: The Series uses outfit changes to reflect the main character’s development. WARNING: OVERANALYSIS AHEAD.
Cassandra’s initial outfit (which will go here because Raps and Eugene’s starting clothes are established in the movie) is plain, subdued, and practical, setting her apart from the other Coronans and the country’s bright and cheery aesthetics, while also signalling her down-to-earth and reliable nature. The dagger on her belt and hidden one in her boot show she’s inclined to violence in her protectiveness and she likes to be extremely prepared and rely on herself. The primary colour being dark red subtly foreshadows her connection to Gothel. Her own style is in all respects at odds with her pastel blue, flowing, lacy, demure handmaiden dress - Cass the handmaiden is not Cass, but purely a front, a box she’s been forced into. The visuals alone tell us Cass really isn’t meant for her job and isn’t thriving there.
Rapunzel’s Season Two outfit is sturdier and more practical than her previous more stereotypical ‘princess-y’ dress and has some darker and more muted colours, even outright black. This shows this season’s more adventurous and serious tone and Raps’s personal increase in courage and confidence, and loss of innocence. The flower in her hair is replaced with a bird pin; she’s traded the symbolism of flowers, growth and renewal, from the renewal of her life as the princess of Corona for that of birds, freedom and daring, bringing to mind the bird imagery in “Set Yourself Free” and the birds that flew past her way back when she first escaped the tower.
Eugene’s Season Two outfit is likewise more… swashbuckling. It’s the vibes, you know what I mean! The blue jacket is more similar to his most-of-Season Three one than it is to the old blackish waistcoat. I’ll get to that in a bit, but basically what I say about that applies here but less so and minus the sun stuff. It’s almost the proto-Season Three jacket.
Cassandra is the only lead not to get any new clothes in the second season opening. Yes, obviously she’s changed a lot since Rapunzel came along (before that her father was the sole positive relationship she had ever, as far as we know, had in her whole life), but in some very important ways, especially to her, she remains stagnant: she’s still in literal legal service to Rapunzel, her existence is still considered inherently subordinate to Raps’s. She goes on the journey to begin with to protect Rapunzel, after all. Her outfit hasn’t changed because, handmaiden vs bodyguard technicalities and Raps genuinely considering her an equal and friend aside… her role as ‘gal pal side character’ in the heroine’s story is exactly the same, and Cass becomes increasingly attuned to this fact. And she isn’t happy about it.
Cassandra’s armour between “Rapunzel and the Great Tree” and “Destinies Collide” represents her reinforced emotional walls, her desire to protect herself from further harm and betrayal by anyone, but specifically her own friends, and most of all Rapunzel, who has just permanently crippled and traumatized her. She finally gets new clothes, the better part of a season late. Just like Rapunzel gets everything first, while she’s left stuck until she can scavage some dead, forgotten knight’s armour. Cold steel physically cuts her off from human warmth and affection. The deep red/maroon cape continues that link to Gothel. I think her disability is important to this outfit. It’s firmer to limit her injured arm’s movement and provides it with better protection and insulation, kinda an improvised brace, thereby giving us an impression of how painful and inconvenient the injury must be.
All of that applies tenfold to Cass’s black rock armour. It is literally indestructible, the way her toxic coping mechanisms are intended to make her, but that only highlights her emotional vulnerability in contrast. The blue right gauntlet draws attention to her formerly crippled arm, a sharp reminder of the pain that drove her to this point. Her skin turns ashen, implying that though the Moonstone cures her arm, it is unsurprisingly for a power of death and decay causing biological damage, to parallel its toll on her mental health. Her theme colour besides black abruptly switches from red to blue, its near opposite. Her dark hair and eyes that connoted how grounded, sincere and trustworthy she was are turned a naturally impossible luminous blue, more intense than her handmaiden dress’s pale blue; her villainy is unnatural and wrong for her like her suppression then was, but far worse. (“Waiting in the Wings”, which spells out Cass’s insecurities that lead to her defection, occurs in a dark shadowy setting lit with blue moonlight, an early glimpse of Moonstone!Cass’s black and blue colour scheme.)
Rapunzel’s Season Three outfit has elements brought back from her old dresses, like the puffy upper sleeves of the Season One princess gown and layered skirt combo with the front parting from Season Two, but it’s more elegant and refined than them both. In a word, it’s regal. It befits at first her role of acting queen, and throughout the season her development into a true leader to her people, developed responsibility and general psychological maturity. The sun symbol’s placement on her chest mirrors Cass’s Moonstone, contributing to the parallels between them this season is brimming with. It may even foreshadow the solid Sundrop’s manifestation there in “Plus Est En Vous”.
Eugene’s pre-promotion Season Three outfit is similarly mature and he proudly wears the crest of the land he used to be an outlaw in on his shoulders, a display of commitment to Corona’s people and wellbeing and his own belonging there. Despite now knowing he’s the heir to the Dark Kingdom, his home is and always will be Corona. That’s a significant step forward after his identity crisis in “Destinies Collide”.
Eugene’s promotion to the captain of the guard brings his character arc full circle. The broken, lonely man who cared only for himself and mocked justice clad in cool blue has become a happy, loved and loving man who fights for justice and the greater good clad in warm red. Again, there’s the Coronan sun.
Cassandra’s ranger outfit combines various aspects of all her previous outfits to show the unification of her fractured personality and acceptance of all her past experiences and actions, the good with the bad: the overall structure highly reminiscent of her original independent outfit, right down to the belt with a small blue pouch on one side; her maid veil tied around her arm; a cape with an asymmetrical oval clasp like in the original armour; a specialized glove on her withered arm like in the black rock armour, possibly her making peace with and accommodating for her disability; and she wears Varian’s cassandrium crystal necklace to remind her of her friends in Corona. The primary colour is green, the true opposite of both Gothel and that miserable, bitter handmaiden’s red, the colour of the growth and life Cass is leaving to engage in. Green is what she wore when she was a tenderhearted little girl, that very shade in fact. She may not be able to restore her innocence, but she can see the world through new, more caring eyes. This is Cass.