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One of my most frequently asked questions recently is how to wear ankle boots with straight leg jeans! Today I’m breaking it down by different styles of ankle boots and showing you some tips for wearing them.

Trying to figure out how to wear ankle boots with straight leg jeans?

As straight leg jeans become more and more popular this year, lots of you are asking how to wear ankle boots with straight leg jeans.

It’s been a bit of a learning curve for me too, and I’m still trying to figure it out, if we’re being honest.

Here’s the truth…

Straight leg jeans with ankle boots are significantly harder to style than skinny jeans with ankle boots. It’s true.

But I tried several styles of ankle boots and several styles and lengths of straight leg jeans and I’m breaking it down for you today so you can see how they look and what to look for and avoid.

How to wear straight leg jeans

If you want some tips on wearing straight leg jeans in general, READ THIS POST!

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • First of all, I forgot to take the third picture…sorry!
  • Secondly, I’m not a fan of this combination. The shaft of the ankle boot is narrow, but not quite as narrow as these jeans demand. So the ankles look a little blocky. Can you see that?
  • This style of jean isn’t great for cuffing, so I wouldn’t do that.  This one is a no from me.

Here’s my conclusion

Now that we’ve walked through three styles of straight leg jeans and three styles of ankle boots, let’s talk about it!

  • There’s no one perfect way. Lots of these options work, and with little tweaks we can make things work better.
  • The outfit will change based on your body type and what you’re wearing on top.
  •  The most important thing is to be able to see the ankle and that its narrower area is accentuated by the boot.

I hope this is helpful as you try to wear ankle boots with straight leg jeans!

(oh, and here are the two tops I’m wearing in these pictures….the purple sweater is old, but HERE is a similar one. The gray sweater is HERE and insanely soft and cozy).

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How to Wear Ankle Boots with Straight Leg Jeans

how to wear ankle boots with straight leg jeans

One of my most frequently asked questions recently is how to wear ankle boots with straight leg jeans! Today I’m breaking it down by different styles of ankle boots and showing you some tips for wearing them.

 

Trying to figure out how to wear ankle boots with straight leg jeans?

As straight leg jeans become more and more popular this year, lots of you are asking how to wear ankle boots with straight leg jeans.

It’s been a bit of a learning curve for me too, and I’m still trying to figure it out, if we’re being honest.

 

Here’s the truth…

Straight leg jeans with ankle boots are significantly harder to style than skinny jeans with ankle boots. It’s true.

But I tried several styles of ankle boots and several styles and lengths of straight leg jeans and I’m breaking it down for you today so you can see how they look and what to look for and avoid.

 

How to wear straight leg jeans

If you want some tips on wearing straight leg jeans in general, READ THIS POST!

 

Now it’s time to break it down by style of jeans and boots

I’m going to show you three styles of boots

  • block heel ankle boots
  • flat casual chelsea boots
  • taller lace up lug boots

with three styles of jeans

  • Shorter cropped length straight leg jeans (in a light wash)
  • Longer ankle length straight leg jeans (in a dark wash)
  • Wider leg relaxed fit straight leg jeans (in a medium wash)
light wash jeans with black chelsea boot

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • I think this one works really well. The shorter length of the jeans and the very narrow shaft of the boot create a little gap at the ankle and a define the ankle nicely so the leg doesn’t look blocky.
  • If it’s too cold for an ankle gap, you can easily add a tall sock under there and fill in the gap. I showed an example of that IN THIS POST.
black chelsea boot with longer leg jeans

What jeans and boots are these?

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • This one also works well. Again, the ankle boot makes it easier to style with any kind of boot because of it’s very narrow shaft. You WANT a defined ankle so you don’t give yourself the look of cankles or blocky legs.
  • These jeans are longer than the lighter wash pair above by about 1 1/2 inches, so they do get a little bunchy above the boot. You can cuff one time if needed!
  • Also fill the gap with a sock if you need maximum warmth.

What jeans and boots are these?

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • The longer length of these jeans makes this outfit a little trickier. See how my leg line looks shorter when you can’t see the narrower part of my ankle because of the longer pant leg?
  • For me, this is a no. If you love it, go for it. But just recognize that even with a great boot, the pants you wear can make the outfit feel less flattering.

 

Let’s walk through the same thing with a different style of ankle boot

lace up boots with cropped jeans

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • Yes, I love this look! I was surprised that the tall boot and cropped jeans style worked so well, but I actually love.
  • The jeans every so slightly bunch at the top of the boot, but I wouldn’t cuff it. That makes your jeans look too short, and with an already shorter crop on the jeans AND a taller boot, it could make your jeans look like they don’t fit.
  • The narrow ankle on the boot keeps the shape of the ankle and that’s a good thing. We want to see that ankle shape!
lace up boots with dark wash straight leg jeans

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • I’m lukewarm on this one. The jeans are definitely a little too long, and they sit over the top of the boot. I don’t like that.
  • I wouldn’t recommend cuffing them, because cuffing above a taller boot makes your leg look shorter.
how to wear straight leg jeans and lace up ankle boots

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • This combination is actually cuter than I expected. A narrow ankle boot keeps that leg line elongated, and the color combination works too with the medium denim and the brown boot.
  • The block heel helps too to elongate the leg line even with the longer jeans, whereas the flat heel black boots that I wore previously didn’t have much of a heel so they didn’t give the same lift.
  • I don’t think I’d wear this, but I don’t hate it.
light wash jeans with tan block heel ankle boots

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • Yep, I think this absolutely works. The shorter length of jeans is great for creating that ankle gap, and that’s the most universally flattering length regardless of the style of boots.
  • And yes, you can fill that gap in with a sock for warmth!
straight leg dark wash jeans with tan ankle boots

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • This longer length of jeans works fine, but I don’t love it as much. There’s no ankle gap here and the jeans and boots touch each other unless I sit down.
  • Since the ankle boot height is shorter, you can absolutely do one small cuff on these jeans in order to shorten the jeans and make this outfit work a little bit better.
ankle boots tan with boyfriend jeans

What jeans and boots are these? 

Does this ankle boot and straight leg jeans combo work? Why or why not?

  • First of all, I forgot to take the third picture…sorry!
  • Secondly, I’m not a fan of this combination. The shaft of the ankle boot is narrow, but not quite as narrow as these jeans demand. So the ankles look a little blocky. Can you see that?
  • This style of jean isn’t great for cuffing, so I wouldn’t do that.  This one is a no from me.

 

Here’s my conclusion

Now that we’ve walked through three styles of straight leg jeans and three styles of ankle boots, let’s talk about it!

  • There’s no one perfect way. Lots of these options work, and with little tweaks we can make things work better.
  • The outfit will change based on your body type and what you’re wearing on top.
  •  The most important thing is to be able to see the ankle and that its narrower area is accentuated by the boot.

I hope this is helpful as you try to wear ankle boots with straight leg jeans!

 

(oh, and here are the two tops I’m wearing in these pictures….the purple sweater is old, but HERE is a similar one. The gray sweater is HERE and insanely soft and cozy).

 

IF YOU LIKED THIS POST, YOU MIGHT ALSO LIKE THESE POSTS

5 Comments

  1. DAYdra says:

    This post is so helpful! What wash do you have in the Everlane JEan?

  2. Kristin says:

    Love this post!! Thank you for all the photos and for breaking it down! I actually get it now

  3. Becs says:

    Love this. What type of socks do you wear with tHe chelsea boot. Too short & they rub my ankle bone, too tall and i cant tuck jean in.
    Also, how do you keep jeans from riding up & out the chelsea boot?

  4. Cindy cramer says:

    I would love some fashion advice, style, colors, and ideas.
    Thanks!

  5. HillarY says:

    Coming in a little late here, but my take away is that there’s no good way to style longer, straight jeans with booties. It looks like the lace up boot is as close as it gets. Is there any way to investigate booties that could pair with the longer straight leg jean more? I ask because it’s what I’m struggling with Haha! And because the Tomcat, 90s pinch, 90s abercrombie jeans seem to fit this way on me, and I’d love some help! Thanks for your posts, they are clearly helpful and needed!

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