Cardcaptor Apparel: Pink with a Hoop Skirt

This outfit was originally designed by Tomoyo with the Fly card in mind, as that’s the card Sakura was up against when she wore it in the manga. In the anime, Tomoyo plans to have Sakura wear it for a “forest dance” in the park to film. Instead, Sakura wears it while going after Woody and Rain. This outfit appears in the chapter “A Cardcaptor is Born Part 2″, and in episode four, “Sakura’s Tiring Day”. It also appears in Tomoyo’s daydream in episode 40.
Main Outfit

Tomoyo sure wanted a lot of close-ups of Sakura in this outfit. The outfit is at its base a pink dress with oversized white trim, and connected arms with gloves.
Circles of yellow keep the main outfit consistent, appearing on the lower shoulders, and the gloves, as well as the back of the outfit. The front of the outfit also holds a yellow-colored plaque featuring the name “SAKURA” (as seen in the manga chapter’s cover image).
Headband

Pink with yellow circles, the headband is color coordinated with the main outfit. The wings are fitting of the manga’s theme for the costume, although they are out of place in the anime.
Gloves

The gloves are part of the sleeves to the outfit. They are fully white with a pink padding with yellow circles on top, matching the design of the shoes.
Socks

Rather than pants to match the long arms of the outfit, Tomoyo opted to go with tall socks. These socks go up just above Sakura’s knees. In the animated design, there’s nothing to suggest the material used for the socks, such as whether they’re made from the same material as the arms of the main outfit. The manga counterpart in one panel shoes lines which may suggest normal cloth used for the socks.
Shoes

Sakura’s shoes for this outfit have soles with thick rubber and gripping. Considering the original “fly” theme, the design looks to support touching ground after falling from a higher-than-normal height. The movement of the shoes in the anime suggests a rubber material is used for the white portions of the shoes, as well.
The choice of white with pink colors matches the style and look of the shoes with the gloves to this outfit, right down to the yellow circle on either side.
Animation Error

At one point in the animation, Sakura’s tall socks are traded in for what appear as white pantyhose instead. The reason for this animation design is fairly obvious, but I can’t imagine the animators couldn’t use a different angle for the scene (camera slightly higher, looking down more at Sakura) or a different position for Sakura to climb over the root. Then again, how else should Sakura move around through a tangle of thick roots when Tomoyo provided her with a hoop to wear around her legs?
Manga Costume

The design used in the anime appears to be a 100% faithful adaptation of the manga version. At one point (not pictured here), Kero is given a collar with a wing symbol on the front, which does not appear in the anime.
Media Use

The manga style of this outfit appears on the case cover to the original Japanese second DVD. Here, the “SAKURA” nameplate is clearly readable, and Kero also wears a “KERO” nameplate.
Thoughts
For the manga, the design works. The wings on the headband give the impression of flight, and the hoop design may have helped slow Sakura’s fall at one point (alongside Kero’s efforts to lower Sakura safely to the ground). If anything, I would swap the tall socks for pants made from the same material as the sleeves, to add symmetry to the design.
I question why the animated episode went with this outfit. Tomoyo’s “forest dance” story feels forced. Who wears a bright pink and white outfit when out in a forest with brown tree trunks and green leaves and green grass and a blue sky? This also gives the impression Tomoyo plans to take Sakura out to film in outfits when not capturing cards, something that’s never touched upon again.
Considering the small spaces Sakura has to squeeze through, going between Woody’s roots, the hoop skirt style is a bad choice. I get the impression the animators choose to use a design from the manga that they might not have anywhere else to use otherwise.
As far as it goes in the anime, the outfit holds up well in water. Amazingly well. So well, it never shows a drop of water on it. Is the material water-repellent? It could be made from a plasticized synthetic resin. It could use rubber. It could even have a textile finishing like a raincoat. All these would sense for an outfit choice if Tomoyo knew about Rain before hand. But she didn’t. It is possible that Rain’s rain is magic, and therefore things do not get wet by it (as neither Sakura’s costume nor the submerged books in the basement appear to be water-touched), which is a better explanation for the outfit’s ability to fair the foul weather. It’s magic, after all. The rain, not the outfit.
Setting aside Tomoyo’s original use for this costume in the anime, the colors work very well together. It’s hard to go wrong with pink and white, and this outfit goes the extra mile by using my favorite shade of pink (and, to be specific, my exact favorite color). I wonder how the design would look if the white trim were not as large-sized as it is. The outfit could probably survive without the headband, or even with the headband sans the wings. Outside of the context of the Fly card, the wings don’t contribute to the outfit any. Just the opposite, without any other wing design as part of the outfit, the wings are distracting.
Considering Tomoyo only had this outfit with her in the anime for Sakura to wear during their picnic, how did Tomoyo fit the outfit into her backpack? The hoop part must fold down some way, but there are no creases or fold marks on it, and it stays stretched out as a hoop rather well. Tomoyo must know laundry secrets to make even Martha Stewart green with envy.