Everything You Need To Know About Wearing Boots With Jeans

Some of the most common questions I get are during the fall… “What boots do I wear with these jeans!? Can I wear these boots with those jeans? Do I cuff them?”
There are so many types of jeans and boots now…it can get VERY confusing! So I’m walking you through how to wear ankle boots with jeans, but more specifically…with each specific kind of jeans… so you don’t have to wonder or worry anymore! Plus, I’m sharing my go-to way to wear skinny jeans and booties…

For more outfit ideas on how to wear boots and boots, make sure you check out this post next.

How to Wear Boots With Jeans

Why It’s So Hard to Decide How to Wear Boots With Jeans

I’ve done TWO videos on how to wear boots with jeans so make sure you watch those here and here if you’re still not sure or have more questions after reading this post! I’m breaking down how to wear ankle boots with different jean styles. But, to make it even more complicated, in addition to different jean styles and hemlines, there are also varying bootie heights and types of booties… Chelsea boots, flat ankle boots, heeled ankle boots, combat ankle boots, etc. Ugh, it can be SO confusing!

But, don’t worry I’ve got you covered in this post! Yay!

More Questions?

If you have additional questions, feel free to ask in the comments.
You can also try out different cuffs and post your outfit pictures in the Hive for positive and encouraging feedback and outfit help from a community of dynamic, like-minded women!

guide to wearing boots and jean

#1 | Skinny Jeans

With skinny jeans and boots, the key is to minimize bunching. Your jeans shouldn’t compete with your boots. With traditional skinny jeans, you have multiple options. (I did a video on how to wear ankle boots with skinny jeans if you want to go back and watch it here.)

With skinny jeans, you have 4 main options (pictured above):

1) Tuck In
2) Small Cuff
3) Large Cuff
4) Double Cuff

Another option is to tuck the jeans under so you can’t see the contrasting colors of the denim.

I show you how to do all of these in this video. Many fashionistas are saying skinny jeans are out of style. And I’ve found myself gravitating toward baggies styles. But it’s still important to have a pair of classic dark wash skinny jeans in your closet as a wardrobe basic. So, I’m sharing a few of my favorites below in case you still need to make those off your list…

#2 | Straight & Tapered Jeans

Straight-leg and tapered jeans have roomier legs and either…you guessed it, go straight down or taper toward the ankle. With either style, you can do a small cuff, large cuff, double cuff, or a tapered cuff. Depending on the pair of straight-leg jeans, I also love to just do nothing when wearing booties with straight-leg jeans. Leave them alone and let them go over the ankle boots. Again, make sure you watch the video to see exactly how I do these if you’re unsure!

1) Small Cuff
2) Large Cuff
3) Double Cuff
4) Tapered Cuff

Straight-leg and tapered-leg jeans are a much more on-trend jean silhouette right now and the perfect middle ground if you’re not quite ready to give up your skinny jeans but also don’t want to wear baggy jeans yet. I’m sharing a few of my favorite options below…

#3 | Wide Leg Jeans

Wide-leg jeans are pretty dummy-proof. Since they’re SO wide at the bottom…you do nothing! This also applies to any sort of flared or bootcut jeans. Just leave them along and let the jeans go over your boots. I LOVE wide-leg jeans and links some favorites below…

#4 | Cropped Jeans

The next pair of jeans I want to tackle… is the cropped jean. Ankle boots and cropped jeans are a match made in heaven. The hemline of the jean is typically not going to compete with the boots, which means you do NOTHING. Yay! Find some chic cropped jeans below…

More Quick Tips for Booties & Jeans

  • Wear taller boots over skinny jeans.
  • With booties that are fitted to the calf, wear the boots under your jeans. This style of booties is perfect to wear under straight, tapered, and wide-leg jeans.
  • If your booties aren’t fitted to the calf and they are taller, more like mid-calf booties, try cuffing your cropped jeans. (works best on skinny and straight-leg jeans)
  • Over-the-knee and knee-high boots always go over skinny jeans. it’s become trendy to wear tall boots and baggier jeans in which case you can let them bunch around the knees. See an example here.

how to wear skinny jeans and ankle boots

skinny jeans and ankle boots Black ankle boots with straight leg blue jeans
black Theory faux leather blazerfaux leather blazer with jeans

Boots With Jeans over 40 fashion

My Go-To Cuff

One large cuff is one of my go-to’s for when I wear skinny jeans and booties. I’m petite so most jeans are longer on me unless I get them in an ankle or cropped length. These jeans by Frame are not cropped so I’m able to do more with them. I did one large cuff and I love how they look with these cute black booties (sold out, similar here). These are the jeans and booties I’m wearing in the graphic above. So you can see how they look tucked in, a small cuff, and double cuffed. All of them work but I love the large cuff for this look!

Faux Leather Blazer… Yes, Please!

I paired the jeans with a lace cami and one of my favorite 3rd layers…a faux leather blazer!

Do you have any other questions about how to wear jeans with boots? What’s your favorite way to wear jeans and booties? Please share in the comments!

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14 thoughts on “Everything You Need To Know About Wearing Boots With Jeans

  1. Love skinny jeans with ankle boots but struggle with height of boot with my skinny ankles. any suggestions would be gratefully appreciated.

  2. Thank you i loved this. i just purchased a beautiful white ankle boot. any specific ideas on how to style a white ankle boot?

  3. Hi, thank you for this info. What about straight legged jeans, with a high heel ankle boot and a flat heeled ankle boot? Lise

    1. Same concept… if the leg is wide enough and the boot skinny enough, wear boot inside jeans. If not, cuff jeans if needed so the hemline is just above top of bootie.
      Same with flat boots or booties. Inside if there is enough leg room or cuff so bottom of cuff is just above top of boot.

  4. Erin this was SUCH a fantastic guide… thank you for writing it and featuring all those different combinations!! I’ll be sharing this in my Best of the Blogosphere post at the end of the month for sure 🙂

    Catherine x

  5. People seem to be afraid of socks! A cute pair of cozy marled socks look great with (not too low) ankle boots.

  6. Thank you for this great video, Erin! I’ve often been at a loss over the jeans vs boots issue. This helps a lot!

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