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Through the different movies and features, Anna and Elsa have been wearing more different outfits than any Disney Princess before and after. Probably a statement based on nothing, but prove me wrong if you know of any Disney Princess with a more extensive wardrobe.
It is difficult to give an exact number of outfits, because it differs the way you count. For example, is the same dress with a different blouse another outfit or not? And, as will be mentioned below, is the same dress but in a much larger size a different one or still considered the same outfit?
Having said that, below are screenshots of all the different attires Anna and Elsa have been wearing in the movies.
Anna
The very first outfit we see Anna wear is her childhood pyjamas when she wakes Elsa to build a snowman.
When we see Grand Pabbie replace Anna’s memories containing magic for memories without the magic, Anna is also wearing a slightly different outfit, more suitable for outside activities.
When Anna tries to get into contact with Elsa right after the gates have been closed, we see her wearing a different dress.
At the beginning of “Do You Want To Build A Snowman?”, Anna is wearing yet another childhood outfit.
Playing with her Anna and Elsa dolls in the same song, she wears yet a slightly different coloured outfit.
A slightly older Anna, once again knocking on Elsa’s door, is wearing yet another outfit.
Talking to “the paintings on the wall”, her outfit changed again.
Teen Anna, walking past Elsa’s door and not even bothering knocking any more, is wearing another dress again.
During, and directly after the mourning ceremony, Anna once again knocks on Elsa’s door, wearing a beautiful and appropriate black mourning outfit.
3 years later, we see the famous scene where Anna is elegantly sleeping with a strain of hair in the corner of her mouth while drooling. Her pyjamas or nightgown is exactly the same style as the one we see in the very beginning of the movie, but due to the much larger size obviously not the same physical pyjamas. So, whether or not to count this one as a new outfit depends on your criteria.
One of Anna’s main outfits for the first Frozen movie is her famous “Coronation Dress” or “Summer Outfit”. This is the dress she will be wearing until she trades it for a warmer outfit at Oaken’s Trading Post (and Sauna).
When searching for Elsa on horseback, Anna is still wearing her Coronation dress, but she added a cape to it. So, again, depending on how you look at it, this can be seen as a different outfit or not.
When tumbling down the hill into the stream, she loses the cape and is in her regular coronation dress again when she enters Oaken’s Trading Post. After meeting Kristoff, who gets kicked out and finds shelter in the barn, she changes into her famous winter outfit that is used to show Anna on most Frozen (1) merchandise.
The winter outfit comes with a headgear that gets lost when Anna and Kristoff fall down the cliff after being chased by Marshmallow, but the general outfit remains the same throughout the remainder of the movie up till the point where Anna presents Kristoff his new sled, where she is wearing yet another summer outfit.
This is the last outfit Anna is wearing in the first Frozen movie.
In Frozen Fever, Anna wakes up wearing a nightgown that has the exact same motifs and features as the one she is wearing in Frozen, but is has a different colour. So, again, depending on how you look at it, it is a new outfit. From an animator’s point of view, it is probably the exact same outfit with just slightly different colouring, but physically a different colour would mean a different piece of clothing.
Anna changed into a summer dress with a sunflower motif. Although Elsa does some sort of transformation to Anna’s dress, all she really does it make it more sparkly and have the sunflowers stand out more than the original, somewhat faded design. So we really consider this the same outfit. If anything, Elsa’s action is more of a “restoration” than a “transformation”.
In Frozen Adventure, we see Anna wear a light blue festive dress with bells and reindeer.
When Elsa finds Anna rummaging through an old suitcase in the attic, Anna added a cape and funny hat to her dress. Not really a new outfit, but we wanted to mention it in here anyway.
Frozen II starts with flashbacks to Frozen I, so naturally, the outfits are all the same as already mentioned above. The first ‘present day’ image we see of Anna is when she joins Olaf on a picknick blanket while she is wearing a beautiful cream-coloured summer dress.
During the charades game, Anna wears the same nightgown she has always been wearing, so no new outfit there. The next new outfit we see Anna wearing is the brown pants and top with a purple traveling cloak that is used mostly on Frozen II merchandise and which Anna wears through the majority of the film.
When Anna and Olaf crash into a cave via a waterfall, she looses her purple cloak. While her outfit is technically still the same, the absence of the purple cape makes it seem like a totally different outfit.
Elsa decides to live in the forest with the Northuldra people and her fellow spirits and Anna is crowed Queen, wearing a nice Queen dress.
Once Upon A Snowman is basically a storyline that happens in parallel to Frozen I, so in the few brief appearances of Anna, she is wearing the exact same outfits she is wearing in the main Frozen I storyline.
So there you have it, depending on how you look at it, Anna has somewhere between 14 and 18 different outfits.