Mississippi is about 1,335 times bigger than Anguilla.

Anguilla is approximately 91 sq km, while Mississippi is approximately 121,489 sq km, making Mississippi 133,404% larger than Anguilla. Meanwhile, the population of Anguilla is ~18,741 people (2.9 million more people live in Mississippi).
Tip: This to-scale comparison of Anguilla vs. Mississippi uses the Mercator projection, which distorts the size of regions near the poles.