This is the best real world picture guide I've found on how to wear ankle boots with jeans.
Here's my best how-to-wear-jeans-with-ankle-boots advice for what I'm seeing:
- Roll your jeans!
Rolled or cropped jeans so a little bit of ankle shows (saucy!) seems the way to go
- Jeans should fit close to the ankle
Then tuck them in so they fit snugly to your ankle, or let them scrunch up. To me, it seems they look best if your jeans fit snugly all the way down your leg, even if they scrunch up then on the bottom
- The opening of the boots themselves should fit close to the ankle
Otherwise it will look like you're a little girl wearing your moms high heels for dress up ;o)