Does this look stupid?!

[Abigail098]

I’m trying to find ankle boots to wear with slim fitting jeans. (Pretty much all my jeans and trousers fit like this.) In summer I wear moccasins, but in winter I’d like to wear ankle boots as they’re warmer and much better for rain. The problem is that the top of the ankle boots gets in the way of the bottom of my jeans, making the jeans look odd (crinkled up on the leg). I’ve tried a few pairs of boots and they all have the same problem. I’ve tried turning up the jeans inwards (not keen on the turned up outwards look), and I think that looks even worse, because my jeans are not skinny enough to look good short. The ideal thing would be to wear jeans that are a really skinny fit, finishing above the ankle, but my calves are just not toned enough for that - really skinny jeans look awful on me. Do you think my jeans look rubbish with the ankle boots?! (One photo is with the jeans turned up.)

By the way, Gabor do those boots season after season, and they are usually in a sale at the end of the season (I got mine in a sale).

I find with a shorter length you don't end up with the ruched gathering on the knee area

I never like jeans turned up unless with sandals/trainers in summer.
I think they cut the leg off at a weird point and ruin the look.

It’s great if you get the hem flush with top of boot - I made an art of this for years before I quit jeans and it is awkward to do, I admit. Hard work, haha.

However, your legs, jeans and boots look fabulous regardless.

Thank you @Abigail098, I do prefer that kind of style.

OP, I think you'd be better off with a calf boot. Something like www.dunelondon.com/wf-rosalinda-ruched-calf-boot1179505060002484/

The jeans are a bit too long for you, skinny jeans shouldn’t be as bunched/baggy as yours are.

You need more of an ankle grazer length. Turned up hems are not “in” - jeans the right length look much better. Turned up hems are outdated and suit light wash mom jeans rather than skinny jeans.

Turned up is fine. But, honestly, you're way over thinking this. No one will even notice

You could just cut them to length, that's what I do.