style session: how to style ankle boots with jeans!

Today I am answering a super popular reader question about jeans and ankle boots! Everyone LOVES ankle boots for fall and winter and when they first reached popularity the jean du jour was skinny jeans… but fast forward to today and the jean styles are all over the place! There is a lot of unchartered territory with jeans and ankle boots these days. I’ve been getting so many questions about what jeans you can wear with ankle boots now that there are SO many styles. From skinny to straight leg to slim leg – what works?? 

I tried on my new suede ankle boots with some of my most favorite jeans recently to do some hardcore research into what jeans work with ankle boots this fall. I myself wasn’t even sure how this little experiment would work – it’s all new territory for me too! So here are my unofficial/official research results. I tried ankle boots with 5 of my most favorite pairs of jeans and are you ready for it!?!? The results are in: there is NO WRONG WAY to wear ankle boots with jeans this fall. I think ALL styles and silhouettes work. Truly!

I will say some jean and ankle boot combos were more to my liking, but none of them looked ‘bad’ really. I liked them all! A few pairs got a tiny cuff at the bottom so they didn’t rub on the boot, but some pairs I just let fall on the boot too. So really… my advice: try lots of looks to get a feel for what you like, but in the end… there are no rules to what works and what doesn’t!

Here are 5 pairs of jeans I would wear with these ankle boots… I’m 5’4 for reference. 

(above) Shown with boot crop jeans
This pair of boot crop jeans has just a bit of a flare at the hem making them perfect for wearing with boots. If you are worried about your hem hitting the top of the boots this pair is ideal.
Shop the look: boots, jeans, sweater, jacket

(above) Shown with straight leg jeans
I cuffed just the hem of this pair to show a little bit of skin between the hem and and the boots. It ends up being the perfect length.
Shop the look: boots, jeans, sweater

(above) Shown with skinny jeans
Skinny jeans are still a great option with ankle boots. Instead of tucking in the hem to the boots I like them a little less ‘perfect’ looking with the hem bumping the top of the boots a bit. It’s not too styled and a little more modern look than how we used to tuck the jeans in. Note: I cut the hem on these jeans back when I originally bought them, the raw hem hits right above my ankle bone for reference.
Shop the look: jeansboots, tank, cardigan

(above) Shown with mom jeans
This is the ultimate modern look right now. Mom jeans are still very much on trend and worn with ankle boots it’s a modern and trendy look that is not a stretch at all to pull off. Paired with a button front top gives it a fun 90’s nod.
Shop the look: boots, jeans, striped top

(above) Shown with slim straight jeans
This slimmer straight leg jeans is the perfect mix between a trendy straight leg and a classic skinny jean. Again I did a tiny cuff of the hem to show a little skin here.
Shop the look: jeansboots, sweater

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