Which are correct?

These examples aren't great but I wanted to try and convey 2 different thoughts. 1 : girl with the prettiest face vs the number of pretty faces
2 The team with the longest haired girls vs the most number of girls with long hair

How would you say this? Is it natural to say 'the country with the girls with' or 'The team with the girls with'?

1
The country with the prettiest women is...
The country with the most pretty women is...
The country with the girls with the prettiest faces is...
The country with the girls with the most pretty faces is...
The country with the girls with the most number of pretty faces is...

2

The team with the girls with the longest hair wins.
The team with the girls with the most long hair wins.
The team with the girls with the most number of long hair wins. This team has 3 girls with long hair vs 2 girls with long hair on that team. This team wins.
The team with the longest haired girls wins.
The team with the most long haired girls wins.

Thank you