To Boot or Not to Boot... Need help choosing!

[Coach Superfan]

So lately I've been contemplating buying some COMFY boots. I was thinking of these type of styles and:

1) I need your suggestions on choosing between these types or any other styles (no Uggs)
2) I need tips on what to wear these boots with (over jeans?) ...

OR...

 

[seahorseinstripes]

i like this :

it'll look great on skinny jeans under it and also on a casual flowy dress!

 

[anotheremptysky]

I just got these boots and they are SO comfy! They have nike insoles and look great with dresses or jeans!

I got mine on sale at bloomies for just over $100 too.