2. "Monster Maroons" from Wrath of Khan through Undiscovered Country

After the tepid audience response to the rather muted and plain uniform designs in Star Trek: The Motion Picture, costume designer, Robert Fletcher, reworked things for the sequel. Thus, 1982's The Wrath of Khan debuted striking, red uniforms with a decidedly more naval feel than what had come before.
I acknowledge that these uniforms fly in the face of much of what I have praised before: They're complicated, they don't look as comfortable, they don't include the clear-cut division colors (though they are present in the undershirt colors), and they're pretty militaristic compared to other Starfleet uniforms. Nonetheless, I really like them.
One thing that these uniforms do is that they offer both visual contrast and visual interest. The deep reds contrast well with the greys and beiges of the ship, helping to draw our attention to the characters. They are also thoughtfully detailed, rather than just visually busy. This adds to the world's depth and encourages fans to delve deeper into the lore if they want, without demanding it.
Another thing about these uniforms is that they add a level of formality and maturity to the look of their movies. Given that the themes of the TOS-era films center heavily around the ideas of aging and finding one's place while growing old, these uniforms feel thematically appropriate. They may be a bit staid and stiff, but this works well for films where the action is more naval/space tactics than fistfights.