It never made sense to me that the rebel cities would continue using the same guard armor mandated by the empire (how else do we explain why every city has the same armor?). It also never made sense to me that the rebels would outfit their entire army in the same attire as every imperial hold guard.

I would instead expect the propaganda machine of Windhelm to model their new guard and army uniforms after "our ancestors, the ancient nords". That's why they'll be using Black Bear Ancient Nord Armor (light for guards, heavy for army officers, and combo of light/beserker for soldiers).

Winterhold is less dramatic about the rebellion; their guards just don't want to freeze to death. They'll now be dressed for the elements, in layers. They get Nord Vagabond Armor (I recommend grabbing the green variant on install).

Dawnstar leans into their identity as a port city that may or may not host pirates from time to time. Enter the Rogue Nord Armor.

Riften having mercenaries as guards sounds ripe for the kind of corruption we'd expect there. Mercenary Light Iron Armor already has some purple in it.

Finally, to bring it all together and make these get-ups look a little more official, outfits also include capes with city appropriate colors and symbols. This mod leverages Cloaks and Capes to do so (I recommend grabbing the upscaled textures).

All 5 of these linked mods are required. You must install them. This mod is only an ESP-FE/ESL pointing outfit records at these other great mods.

This mod is ESL and the 4 gearshout armors mods are also ESL.

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Compatibility Notes:

1. Cloaks - Cloaks of Skyrim vs Cloaks and Capes - I believe you can have both installed just fine.
2. Body - CBBE/BHUNP/ASDFASDF - it shouldn't matter. All of these armors cover the whole body. You can install the CBBE version of these armors if you like, but it also works fine to just install them as is.

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Credit:

So much thanks to Gearshout and volvaga0 for creating the beautiful and lore-friendly armors and capes this mod depends on!