Sakura wears this in episode three, “Sakura’s Heart-Racing First Date”. I don’t understand the jester theme to the outfit, but maybe that’s just what it is: a theme. Does Tomoyo sit around thinking, “What would Sakura look like in a jester swimsuit”? Maybe she thought, “What did court jesters swim in? Oh, I have to make a jester swimsuit for Sakura to wear!” This outfit isn’t visible in Tomoyo’s van of costumes in the second episode, so it’s possible she threw an idea together quickly after learning the enemy would be water-based.
The core of the outfit looks like (and may be) a blue swimsuit, with a collar (not seen under the white piece of the outfit in the anime). This is sensible as there’s always a chance Sakura will be submerged, or at the very least violently splashed at, by the watery Clow Card she’s about to face. In the manga, Sakura had already almost drowned by Watery in the school pool before Tomoyo used her own limited (lack of) swimming ability to go in and pull Sakura out.
Worn over the basic swimsuit is a white piece with a collar and a skirt in a “jester’s collar” style. The ends of the skirt are longer in the back.
The ends of the collar and skirt are silent, so they are adorned with decorative yellow balls rather than bells. Wide shoulders of the outfit allow for free movement of arms.
Hood, Gloves, and Shoes
To match the color and theme, Sakura’s outfit includes a blue twin-hooded jester-style cap, long blue gloves, and blue pointed shoes. Both the hood and shoes include the decorative yellow balls at their tips. The hood also has a yellow ball design on either side of the white trim. The white at the openings of the shoes matches the hood’s white trim in color coordination.
This accessory for Kero deviates from Sakura’s in specific style, but matches the theme. Sakura might have had a similar collar to her outfit if Tomoyo either 1) thought it wouldn’t be bothersome when running and flying, or 2) didn’t think the chosen design would make for a better design. I’m guessing it’s the latter.
The light blue color for Kero’s collar is interesting, as Sakura wears solid blue in her outfit in the anime. Her manga counterpart wears a more pastel blue, closer matched to Kero’s collar color, but in the manga Kero wears a white color.
Just the same as the collar and skirt on Sakura’s costume, Kero’s collar ends in yellow balls, which are probaby also not bells. If they are bells, on both of their costumes, then they’re designed without the object inside to make a jingling noise.
The manga version of Sakura’s outfit has a transparent outer piece, making the swimsuit underneath a much more visible portion of the design. Since I don’t know of any transparent cloth, this outer piece may be plastic, similar to plastic used in inflatable float rings used in the water by non-swimmers to stay afloat.
I imagine the outer piece’s design was avoided in the anime to make it simpler to animate.
Color differences include a powder blue for Sakura’s swimsuit portion, and white gloves, with clear wings adorning Sakura’s shoes.
The manga style of this outfit appears on the case cover to the original Japanese first DVD.
A swimsuit against a water card is a well met match. The opaque white covering in the anime version looks fine with the jester theme, but I prefer the manga version, if only because the visibility of the swimsuit gives a stronger impression of the outfit being fitted for the situation.
Strangely, the gloves to this outfit extend past the elbow, but the shoes are barely higher than the ankles. I don’t know style, but I would imagine the shoes might be better if they extended up high, matching the style of the gloves.