Ankle boots are my JAM. Seriously, fall is my favorite because of B-O-O-T-S! Sometimes wearing boots can be tricky. I have different pairs of denim I wear different ways with different pairs of boots, and today I am breaking it alllll down for you guys. Seriously, this might be a little too detailed but let me know if you have any questions.
Hi! New here?? I’m so glad! This post is getting lots of traffic from Pinterest, so I thought I would take a second to introduce myself. I’m Amy Ann, mom and wife, and I love sharing my everyday life and fashion here. I’d love for you to follow along on Instagram, Facebook, or Pinterest. You can also find similar posts to this one about how to wear ankle boots with straight leg jeans, when to tuck and not tuck your shirt and what shoes to wear with cropped jeans. Now back to boots. 🙂
How to Wear Ankle Boots with Jeans – The Dos & Don’ts
Cropped Denim
This is perhaps the easiest way because your jeans do all the work for you. If you are wearing a cropped pair of jeans, they are already not going to conflict with your booties.
- Do let your denim hit above your booties
- Don’t let there be too much skin between the bottom of your jeans and the top of your booties. This may mean (depending on how cropped your jeans are) that you need a taller ankle bootie (one that hits above your ankle bone) as opposed to a shorter pair. In both pictures below, I am wearing one of my taller booties.
Examples
Tuck Your Jeans In Your Boots
This one is the trickiest of all in my opinion.
- Do tuck your denim when it is very skinny at the ankle and will not bunch. It also has to be long enough to tuck.
- Do tuck your denim when your boots have a wider opening at the top.
- Don’t try to tuck your denim when your boots are very short (i.e. hit at your ankle), only when they are a bit taller.
Example
Cuff Your Denim
Jeans that are 1.) too long to naturally hit above your booties 2.) not super skinny at the ankle and/or 3.) may be paired with taller booties are great candidates to be cuffed. My jeans below are a great example because they are a thick denim that is pretty long and not super skinny at the bottom. Any bootie I pair them with really means they need to be cuffed because it causes them to bunch.
Do cuff your jeans when they would otherwise bunch over your booties.
Examples
Do Nothing
Sometimes your jeans are just regular length skinny jeans and your boots are ankle length, and there is no need to cuff or tuck. Win!
- Do nothing when your jeans are skinny/narrow at the bottom and hit just above your ankle.
- Do nothing when your booties hit at your ankle.
Examples (sorry for a throwback pregnancy one, best I had! Miss those jeans…)
Like this post? Be sure to follow me on Instagram and sign up for my newsletter here for more content like it!
Ankle Boots I’m Loving
Jeans I’m Loving UNDER $80
You Might Also Like
112 Comments
I am 68 years old and very happy to read this article as I still want to look fashionable! Thank you thank you thank you!
Stop it with the skinny pants, not everyone can wear them or should. I guess, I am of the variety is the spice of life kind of girl.
Hi Olivia,
I am sorry you found this so distasteful. Feel free to read another blog or one of my many articles about other jean styles.
Thanks,
Amy Ann
No one is forcing you to wear skinny pants. With the entire fashion world at your fingertips, spend some time elsewhere if you don’t like it.
omg! just move on. so rude
I for sure needed this post. I have so many cute boots and so many cute pants but struggle to put outfits together because of this. Thanks for the advice! Love the pics!
Hi! I believe I responded to you directly over email, but thank you SO MUCH for taking the time to leave a kind comment. I am so glad it was helpful and hope you have a wonderful day!
Hi Amy Ann
l dont think Kim was personalising her ‘chicken leg’ comment. l think l know what she meant. l am 5’1″ with really skinny ankles and l need to pay attention to where jeans. skirts or boots hit – also the width of boot tops can be a problem for me.
l think we all realise that your ‘tips and tricks’ are generic and not specific – they cannot be – we are all different shapes and sizes. Love your Posts – l can always find something l can relate to and that helps me to keep ‘on point’
Thank you
Amy Ann – l thought fashion was a fun thing not a stick to beat someone with. Some of the comments posted for your jeans boots Blog quite frankly are completely ‘out of order’ All you are doing is giving guidance and ideas that we can pick and choose from to suit our personal style and our life style. l would suggest that if some readers need to take everything literally maybe they need to develope their personal style then use your excellent blog to give ideaa and suggestions.
May l suggest not justifying those comments by taking the trouble to reply if those comments are not in the spirit of your blog.
Go Girl! You are absolutely correct. Every one of us is different (thank Goodness), has a different body shape, style, and idea about what we like. Different strokes……and all that. Thanks Amy Ann for your suggestions! BLT
I love your tips but im only 5’2” 😔
Do the same principles apply to me even though I’m short.
I’m also size 12 (UK) so not really skinny either.
thanks..
however skinny jeans with pointy heel boots look so old fashioned such as what I wore in 2013. Where is wide pants, big boots, slouchy being the new sexy. Your ideas are the stereotypes of female sexy. Do something new-age.. different..origial.original.. Avant garde.
Not boring .
Be nicer. Or just move on.
👏🏻👏🏻👏🏻👏🏻👏🏻
I agree!!!
I agree A Mom!
I agree,if you do not have something nice to say, then move along.
Thank you all for taking the time to leave kind comments! Some of these have gotten pretty mean. I have responded to many of them directly over email (well the kind ones anyway). I have MANY articles on my blog about all kinds of jeans. Everyone has different tastes. Styles also change over the years too. Thank you all for reading, and I hope you have a wonderful day!!
love your suggestions …They are all right on.. Just the way I like mine to look.
I dont think wide pants have caught on as much as the designers thought they would. I love the look of slim pants with heeled boots. You had the best examples right here.
Yes good on you Mom I’m tired of the nasty all over the place. Shut up and move on.
WOW. Well I think we solved the mystery of where all the wide pants and big boots are. hiding out…obviously in your oh so fashion forward slouchu and sexy closet! Sounds like YOU should start a blog, Minister. I’m sure you’ll enjoy reading it. 😉
*SLOUCHY* and *MIMISTAR*
I couldn’t care less about what’s in style now. I wear what I think I look best in. I like the slim fit ankle length jeans and pants. I don’t like the high waist, baggy look for me, although they look good on others.
Thank you. I appreciate your advice and get a kick out of some comments. My weight fluctuated in the past and skinny jeans were not flattering so personally, I would have looked past your blog and found one the worked for me instead of finding a reason to complain. As it stands, I am now able to wear skinny jeans. So, THANK YOU for the fashion forward. I’ll be putting together an outfit today that will be hot, hot, hot!
I am 40 yrs old and absolutely love this article as I have been trying to better my self esteem. I do like to wear the ripped jeans as it is 2022 and they are totally in style now! You have given me amazing tips!!! Thank you so much!!!
This makes me so happy to hear! Thanks so much for reading and leaving such a kind comment! Have the best day!
I find the best thing is to wear what makes you feel good and ignore these experts views. After all who voted them in as experts in everything.
Absolutely <3
I don’t care for the denim hitting above the ankle, and a wider boot body at the top. Makes legs looks like chicken legs flopping in the boots 😂
Hi Kim,
I am sorry you find my ankles to look like chicken legs flopping around. I am 5’10 and thin. My ankles are on the smaller side, and that is what they look like in every boot I own.
I hope you have a good week and thanks for reading.
Amy Ann
You look amazing! Ignore the negativity! People can be so annoying! Keep up the good work! Very helpful to me!
I agree people stop hating on skinny people not all of us choose to be this way we’re just stuck with it!!
You could have kept scrolling . There is no need to be rude .
You are very welcome <3
I’m stumped,I’m 73,like to be stylish,and cannot wear much of a heel,anymore,please help give me advice!
Hi! You can absolutely wear flat boots and use these same principals. Most of mine just happen to have a heel, sorry!
Hi Amy Ann
l dont think Kim was personalising her ‘chicken leg’ comment. l think l know what she meant. l am 5’1″ with really skinny ankles and l need to pay attention to where jeans. skirts or boots hit – also the width of boot tops can be a problem for me.
l think we all realise that your ‘tips and tricks’ are generic and not specific – they cannot be – we are all different shapes and sizes. Love your Posts – l can always find something l can relate to and that helps me to keep ‘on point’
Thank you
Thanks for your help with booties & jeans, you clarified my confusion!
I know as an old lady I appreciate tips & advice on current fashion trends and how to wear them if appropriate for Me.
Please ignore the nasty comments, it’s a sad way to be treated, it’s a reflection of them and their unhappiness. Don’t let Anyone steal your joy!
My Sister is a plus size gal, she bought her some black ankle booties. She wears them with her jeans , she cuffs them up at ankle and she looks pretty cute.
Do not be sorry for the pregnancy pic! Gosh! Pregnant women want to know these tips too!
I love the pregnancy ones! I’m currently 16 weeks with my first and struggling to stay stylish haha! This helped heaps. Thanks!
I will be glad when this fad passes…..nothing like taking your legs and cutting them off at your ankle….what happened to the days of long and lean looks. This is one fad I pass on…don’t like the look and you need to be 5’10” with long skinny legs to pull this one off……
Love these tips! Would love a tip on how to ‘roll’ a cuff … as in a a slouchy cuff. I’m a petite women and often have to cuff a few times but love for the unfinished hem to still show. Any ‘cool’ way to do? Thanks!
your so adorable with your little baby bump! Great tips..
your so adorable with your little baby bump! Great tips..
hello, does anyone else think that ripped up jeans with your knees sticking out is the DUMBEST TREND that has come along in many years???!!??! Why do we do this???…It looks ridiculous! I love the boots & jeans tips…& just signed up to follow you, thanks!
Thanks so much for following along and for leaving a comment. So glad you found this post helpful. Sorry yo udon’t like the trend of the ripped jeans. I totally understand that. I personally like it, but I know it is not for everyone. Happy Thanksgiving!
Don’t apologise for your pregnancy! Own it 💪
I agree! But I have a better one to make you crazy — jeans hanging halfway down the butt!! What were they THINKING? Love these boot styles – am going to repurpose a few now!
Yep! That and putting books backwards on shelves drives me nuts!
It’s nothing wrong with the ripped jeans the one I can’t stand is the low waisted jeans showing the crack of woman butts again I rather have the ripped. jeans all day and I’m 62 1/2 y.o but look about 40 y.o
Yesssss! I love me some ripped jeans and even better if they are high waisted lol and I’m 40 almost 41. Anymore I don’t think I even own a pair of jeans that’s not a mid rise or high lol and I only own 1 pair of bootcut jeans, the rest is skinny jeans and most of them are ripped lol now a few years ago I would not even think about skinny jeans but I think they are definitely giving me a confidence boost <3
Agree , what is interesting about a book backward. It looks silly.
I thought it was just me. I like a more put together look the “ripped” style . I would never, ever purchase a pair of torn britches.. lol…
What advice do you have for knock needed women? What kind of jeans should we wear?
Hi! Thanks so much for stopping by and leaving a comment. I just sent you an email.
What’s knock needed?? Never heard of that!
When legs are shaped in a way that the knees touch together, and lower legs are out further than knees
I see this post is over a year ago! You probably know what it means by now!
It’s ‘knock KNEED’, not need. Because the knees knock or touch each other.
Do these rules also apply to plus size girls?
I responded over email, but yes! I think they definitely do. 🙂
The black, pointy toe leather booties in your post– where can’t I find those?
Great advice on how to wear….
Thank you
Great tips I was so worried about cuffing my jeans to hit above the booties. But it does look great
I dont think wide pants have caught on as much as the designers thought they would. I love the look of slim pants with heeled boots. You had the best examples right here.