Today's little cutie is a runt from Sweden who became an international sensation. There was even an American remake in the 1980's. Who else am I talking about but the adorable little Pippi Longstocking!~
Pippi was also a pirate, you know, so don't be surprised when she's wearing a cliche pirate hat and an eye patch.
To add a little bit of Pippi Longstocking into your Lolita coordinate, part your hair down the middle and section it off into two simple braids. All the better if you can get them stick up like hers! Multicolored thigh-high socks are a great option as well, especially if they're different patterns or designs. Simple boots are best for this.
This can work well in Sweet Lolita, Country with gingham dresses, and even simple Gothic. But taking a Pippi approach to Pirate Lolita could be a lot of fun. I bet not many people rock braids like those with Pirate Lolita.