I'm probably biased since I like short hair on women in general (Whether it be Anime or IRL)
But there's something about the new look that grabbed me immediately. The design just pop's and quite literally unique since Anime Serena's outfit and hair cut aren't options in the games.
Short hair chestnut hair accented by the reddish-pink fedora, The pink one-piece dress contrasting beautifully with the blue ribbon that's the centerpiece of the entire look, accompanied by the red sleeveless jacket, dark grey stockings, and those boots...
It looked perfect, it honestly and made me fanboy for a couple of minutes when I first saw it.
I feel that the OG outfit doesn't fit her at all. Since her proportions really aren't similar to her Video game counterpart, the outfit becomes bland and unnatural to look at times. Her figure just wasn't suited for her outfit I feel, the long hair also didn't help since at times it made her look thinner than she already was... not to mention making her head look bigger body at times...
The Black as a primary color also didn't fit well with her, with Pink or Red honestly looking better on her hands down, long hair or otherwise.
Also since we're talking about design, here some of my fav serena fan art XD