How to Wear Ankle Boots with Jeans and Skirts

Last week I started a short series on how to wear ankle boots based on a few of your questions from the Style Help Survey.  We talked about different kinds of ankle boots, and I showed a bunch of pairs and talked about why I did or didn’t like them.  (Catch the last post HERE.)

Today we’re talking about how to wear ankle boots with jeans and skirts/dresses.  I’ll start with jeans because I feel like that has been the more difficult area for me.

Several people have asked what the “rights” and “wrongs” are of ankle boots.  I’ve read handfuls of articles saying certain things are wrong, but I’ve seen many people break those rules and look really cute doing it.  I think there are actually many “right” ways to wear ankle boots, and a lot of it comes down to preference and what kind of look you are going for.  However, if that doesn’t relieve your stress and you still want someone to give more guidance and clarity, I’ll try today.

With Skinny Jeans

So, the honest truth is that I haven’t loved how my skinny jeans have looked with ankle jeans.   (See all my ankle boot outfits HERE, HEREand HERE.)  I usually do a “messy roll” with them, which I don’t necessarily think is wrong, but I’d prefer the look to be tighter and neater, like this:

Finally, I stumbled upon an amazing post from Amanda at Advice From a Twenty Something, which you all need to check out HERE.  (The pic above is taken from that post.)  This is my favorite tutorial on how to wear ankle boots with skinny jeans, and she shows 4 ways to do it.  It’s clear, beautiful, and overall incredibly helpful.  Amanda’s post will probably be enough for most of you, so if it gives you the answers you need then go on and look cute with those ankle boots!
However, I tried to do what she said and it still didn’t solve my problems.  If you are still having problems here’s the thing: make sure your jeans are skinny enough at the ankles.

Skinny jeans tend to fit me like the picture on the left, not completely fitted to my ankles without alterations.  This looks fine with flats or pumps, but it becomes a problem when I roll them for ankle boots.  The picture on the right shows the same pair of jeans made skinnier with binder clips on the back acting as if I altered them.  It’s a subtle difference unrolled, but it gets magnified once the rolling begins.

(I’ve gotten lots of emails about what kind of binder clips I used.  Please note that the binder clip thing is not an actual solution!  It’s just to illustrate the difference in the pictures above so that I could use the same pair of jeans.  I literally have binder clips sticking out at my ankles, haha!  You need to get your jeans altered if you want to make the leg more fitted.  🙂  )

On the left column are the single and double rolls with my jeans in their natural state.  On the right are single and double rolls with the jeans “skinnified” (aka binder clip).

The bottom left (natural double roll) ended up giving a tighter look without having to alter my jeans.  It’s still not as tight as skinnified jeans, but it’s something to try if you don’t want to pay for tailoring.

Like I said before, I don’t think the looser rolls on the left column are necessarily “wrong,” but I’m usually always trying to get the cleaner lines on the right.  I also think the skinnier legged looks are easier to pull off in the sense that you don’t have to worry as much about the cuff cutting off your leg line because they’re not sticking out past the width of the shoe and creating a more defined line.  Instead, a skinnier leg makes things a little more streamline.

Here are comparison pics with an even taller boot that covers my ankles completely.  Again, it’s really a matter of preference, but this was for those who have been trying to get the looks on the right and haven’t been able to figure out why their jeans weren’t working.

If you try this look with straight legged jeans, you will probably get a more extreme version of the looks on the left.  Also, if you try this with jeans that go past mid-ankle it’ll probably be hard to get a decent 1-roll look, and multiple rolls might get bulky depending on how long your jeans are.  

Shop for the Look:
Top: J.Crew Factory (exact–wearing S, similar)
Jeans: Nordstrom (exact, similar, similar)
Boots #1: Old Navy (exact, similar, similar)
Boots #2: Forever 21 (similar, similar)

(The lighter brown suede boots from Old Navy HERE looked cheap online, but were MUCH better in person!  Doing a review of them soon, but ON is currently 40% off for today only!)

With Trouser Jeans
All that said, I think it’s hard to do a rolled jean look with straight legged jeans if you are concerned about cutting off your leg line.  If you don’t like skinny jeans, you could also wear booties with trouser jeans.

This is my favorite pair #4 from the last post–the pair with the cutout in front.  The toe is slightly pointed, and I think if they were pointier it would have looked even better with trouser jeans to elongate the leg.  If your ankle boots look a little strange with trouser jeans, try a pair with a pointier toe.  

With Skirts and Dresses
I find that regardless of the cut of the dress (pencil, a-line, or whatever else), the thing that makes or breaks it for me is the length of the dress.

Above are a-line skirts at different lengths: midi, knee, above the knee.  My preference with FLAT ankle boots like these is slightly above the knee, though at the knee is okay too.  However, if I’m wearing a knee length skirt or dress I’d prefer my heeled cutout boots like below on the right:

I mean, this boot can really do no wrong.  (Except that it has heels and sometimes you just really want flats no matter what…)

Shop for the Pieces:
Tee: Everlane (exact–wearing M)
Midi Skirt: c/o Le Tote
White Skirt: ASOS (exact)
Above Knee Skirt: MNG via JCPenney
Boots #1: Old Navy (exactsimilarsimilar)
Boots #2: Target (really old, but similar HERE)

If you wear a high pair of boots, adding tights that match will extend your leg line and help prevent your legs from looking stumpy.  Example:
The boot goes a couple of inches past my ankle and really cuts off my legs.  Even a hem above the knee couldn’t help much.  To minimize that, I went with matching tights.

Alright, that might be information overload.  Here’s a summary:

  • Go to Amanda’s post on ways to wear ankle boots with skinny jeans from Advice From a Twenty Something HERE.
  • Make sure your jeans are skinny enough at the ankles if you want that look.
  • There are a lot of “right” ways to wear ankle boots and it depends a lot on your preference.
  • If you don’t want to wear skinny jeans, pair ankle boots with trouser jeans, but go for a pointier toe.
  • For skirts and dresses, aim for hems that hit at your knee or slightly above.
  • If the boot is high, pair it with same colored tights to extend the leg line.
  • When all else fails, an ankle boot with a cutout front is awesome.  (Found one sort of similar pair HERE.)
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  • Reply
    Lindsay Erin
    September 23, 2015 at 8:13 am

    Where is the tunic from in your last pic?! I love it!

  • Reply
    the cape on the corner
    September 23, 2015 at 8:41 am

    such a helpful post, and i love the way you broke it up with the pictures to really define what you were saying with the different examples. simple to understand and see what works and doesn’t. more of these, please!

    • Reply
      Audrey @ Putting Me Together
      September 23, 2015 at 11:13 am

      Thanks, b! I’m working on doing more posts like these. They take a lot more time, but I think they’re more helpful than my OOTD posts. Glad to hear you like them!

  • Reply
    Aubrey Bardsley
    September 23, 2015 at 9:17 am

    Thanks for this post! So I’m trying to prep for winter here in Utah, and I’m wondering how to wear my ankle boots with the snow. Obviously the rolled up, little bit of ankle showing look won’t work when it’s so freezing. Any tips?

  • Reply
    Aubrey Bardsley
    September 23, 2015 at 9:18 am

    Thanks for this post! So I’m trying to prep for winter here in Utah, and I’m wondering how to wear my ankle boots with the snow. Obviously the rolled up, little bit of ankle showing look won’t work when it’s so freezing. I’ve looked all over and can’t find anything. Any tips?

    • Reply
      Audrey @ Putting Me Together
      September 23, 2015 at 11:12 am

      I’ve seen people do a thick scrunched up sock. I can’t speak much on it though because I’ve never done it and wouldn’t be able to recommend the right sock. However, I THINK I might have seen a tutorial on socks + ankle boots on Advice From a Twenty Something. I’d do a search for it and see if there’s anything.

      • Reply
        Aubrey Bardsley
        September 23, 2015 at 12:13 pm

        I’ll check that out, thanks so much!

        • Reply
          September 23, 2015 at 10:27 pm

          Yes, the thick socks/ankle boots combo is a lifesaver in the cold months! My favorite socks in recent years have been the Smartwool super-cushioned hiking socks (really warm and unbelievably comfy) or LL Bean’s Ragg socks.

          • Aubrey Bardsley
            September 24, 2015 at 5:35 am

            Thanks Mary!

  • Reply
    September 23, 2015 at 9:25 am

    These posts are really helpful and show me how clueless I really am! Yikes!

    • Reply
      Audrey @ Putting Me Together
      September 23, 2015 at 11:10 am

      Haha, took me a while to figure out the skinny ankle thing, so we’re in the same boat. At least we are in it together. 😉

  • Reply
    bitch i might be
    September 23, 2015 at 10:08 am

    I do the rolls with jeggings but they don’t look as nice as I’d like. I think it’s because 1) I’m 5 ft and most jeans don’t hit at the ankle and 2) my jeggings aren’t lighter denim when inside out so it doesn’t have that contrast. They are just slightly lighter than the outside. I’m sure the solution is to get new jeans but that’s a whole other issue. 😛 Great post!

    • Reply
      Audrey @ Putting Me Together
      September 23, 2015 at 11:10 am

      Ah, I didn’t even take into consideration the lighter fabric on the inside. That does make a difference!

      And yeah…the length is a big factor for me too. I need to tailor a lot of my jeans. I’m sure at 5′ it’s even harder to find the right length of jeans!

  • Reply
    September 23, 2015 at 10:39 am

    So helpful! Do you have any thoughts on what color ankle booties to get? Black seems to go with everything, but I’ve also heard that a neutral bootie won’t cut your legs off as much?

  • Reply
    September 23, 2015 at 10:58 am

    Thank you for this very comprehensive post. You are a perfectionist! For me, wearing ankle boots with skinny jeans is always a trial and error game. Everybody has to find out what works best for her. Andrea

  • Reply
    Diana @ Bumps Along the Way
    September 23, 2015 at 11:22 am

    I love these ankle boots posts! I just bought my first pair and still haven’t worn them but am very excited/nervous!

  • Reply
    September 23, 2015 at 11:23 am

    So helpful! My question is… what color tights do you wear with tan ankle booties? I like your dress and booties example but what about when it’s cooler…what tights? thanks!

    • Reply
      Audrey @ Putting Me Together
      September 23, 2015 at 12:39 pm

      How about brown? If I don’t need the tights to match the tan booties (like, the boot is lower vs. the high ankle ones I talked about) then I’ve worn grey, maroon, and brown.

      • Reply
        September 23, 2015 at 1:05 pm

        i love the idea of maroon! thanks 🙂

  • Reply
    September 23, 2015 at 1:16 pm

    I’m with you on the not always loving how mine have looked in the past and finally figured out the ankle openings needed to be skinnier to work right. But to work with the jeans I have… maybe I just start walking around with binder clips?!

  • Reply
    Sophie Ford
    September 23, 2015 at 3:59 pm

    This post puts into words and explains why I hate wearing my black boots with anything other than black jeans or leggings, I just could never figure out why. How you explained it cutting off the legs and making a line makes so much sense!

  • Reply
    Rosemary Bostic
    September 23, 2015 at 7:28 pm

    Great post!! I always get a little nervous when wearing a ankle boots with skirts, but they look so cute on you here!!!

  • Reply
    September 23, 2015 at 8:45 pm

    Love this post! As an addition, I’ve found that rolling jeans that are looser around the ankles can work if the jeans are a more relaxed fit overall – ie my boyfriend jeans. With a slightly thicker cuff and enough skin showing (about an inch to an inch and a half of skin works for me), I’ve found I can pull off the look. Also, on a completely different note, could you maybe post a list of suggestions for olive skinnies? I’ve been looking for an new pair this season and am not having any luck.

  • Reply
    September 24, 2015 at 12:35 am

    Such a helpful post especially with all of the detailed photos! I just started wearing ankle boots a few weeks ago and you would think that cuffing jeans would be fairly easy, right? Wrong! I felt so silly doing a Google search on how to cuff/roll my jeans with booties but it sounds like I’m not alone in this. Now I’m off to play dress up with my new boots using your suggestions. 🙂

  • Reply
    Prudence Yeo
    September 24, 2015 at 1:07 am

    I love how ankle boots look with flare jeans (chic) and skirts (cute)! And it’s a good idea to fold up skinny jeans even when it may appear a little loose, thanks for the inspiration!


  • Reply
    September 24, 2015 at 6:13 am

    This is such a helpful post. I kept wondering why my jeans looked so messy and frumpy when I rolled them, and I thought I was doing something wrong.

  • Reply
    Suzi L.
    September 24, 2015 at 7:18 am

    Wow! I honestly can’t believe that so many people are trying to conform to the “right” way to wear any article of clothing. They are boots people. If you like it, then it looks fine. If you try on a pair of boots and you don’t like how they look, don’t buy them. Easy peasy. Isn’t part of the definition of “style” how any given person actually wears an item. And a second thought follows that one, isn’t part of the reason we are on this journey together to attempt to find our own “style”. Don’t get me wrong, I do appreciate the technical tips and tricks (you’ve done a fabulous job of sorting this out!) but, I think we could all benefit from a bit of confidence in our own ability to discern what looks nice and what doesn’t. Am I wrong?

    • Reply
      Audrey @ Putting Me Together
      September 24, 2015 at 7:45 am

      Hi Suzi. Thanks for your thoughts. I really appreciate the sentiment you shared of wanting people to find their own style. I usually try to write general concepts and not tell people they HAVE TO do things a certain way (with a few exceptions). This particular post was written to help people troubleshoot why they might not have been able to get a particular look they were going for, but my intention was NOT to tell them that the other look was wrong. I tried to make that clear by saying several times that I didn’t think the loose fitting cuff was wrong, but that if anyone WANTED the tighter fit and couldn’t get it, then to try jeans with skinnier ankles. I hope that distinction makes sense, and if it could have been clearer please help me know how I could have done that better.

      • Reply
        Suzi L
        September 24, 2015 at 9:02 am

        Hi Audrey,
        I love this blog and I read it most every day. I really do appreciate this post and your sense of style or I wouldn’t still be here. : ) I just thought that it was important that we remember to have the confidence to have fun with fashion. Part of that confidence comes from discussions like this one and from seeing the options that are out there. Thanks again for all you do!

  • Reply
    September 25, 2015 at 12:40 pm

    I’m digging around to see where the trouser jeans are from. Did I miss it? I love them!

    • Reply
      September 25, 2015 at 12:41 pm

      Ah. Just noticed the shorter hair in the photos… so probably an older closet staple you get to bust out again.

  • Reply
    Susan Scott
    October 8, 2015 at 4:19 am

    Have you tried pegging your jeans to get the skinnier ankle fit? Anybody who was in high school in the late eighties can show you how to do it.

  • Reply
    November 13, 2015 at 8:20 am

    What about jeans that aren’t skinny or trouser cut? I have some that are close to skinny but NOT. They are VERY long and I need to cut and re-hem but not sure what to do then. Do I re-hem so one inch of skin shows? Or do I re-hem so I can cuff once? Or is it even good fashion to show skin above the bootie with a jean that isn’t skinny? Any advice would be appreciated!

    • Reply
      Audrey @ Putting Me Together
      December 2, 2015 at 8:19 am

      I think you should figure out if you would wear the jeans more with heels or flats and hem them accordingly. Then, wear them with booties however need be, whether it’s cuffing once, twice, or not at all.

  • Reply
    January 22, 2016 at 5:38 pm

    Where did you get the shirt/tunic you’re wearing with the tights in the last picture?

  • Reply
    March 22, 2016 at 3:52 am

    Going to buy my first pair of ankle boots, I would only wear them with jeans, would you recommend brown or black. Also what kind of leather, the smooth finish or suede? Thanks

    • Reply
      Audrey @ Putting Me Together
      April 3, 2016 at 7:54 pm

      Hi Dee! Sorry this is such a late reply! You might have already gotten your ankle boots. Brown or black just depends on what the main neutrals are in your closet. (See here: If you wear both brown and black equally then you probably couldn’t go wrong with either!

      I tend to go for suede ones because they tend to be a little more subtle and casual. But really, both would be good depending on what you’re going for. I hope you found a pair you love!

  • Reply
    October 11, 2016 at 8:01 am

    Please tell me what kind of “binder clips” you are using, and exactly how to use them? Love that look!!!!!

    • Reply
      Audrey @ Putting Me Together
      October 11, 2016 at 10:27 am

      Oh! Haha I would not wear pants with binder clips out in public. It was merely to illustrate the difference in these pictures since I didn’t have jeans that were skinny enough when I wrote that post. No special binder clips and no special way to wear them without looking like you are wearing binder clips on your jeans, hehe. Gotta go buy jeans that have a skinny leg opening!

  • Reply
    Brianne Austin
    January 29, 2017 at 12:05 pm

    What about combat boots? They are higher than the ankle boots and I’m never sure whether to roll my jeans or tuck them.

  • Reply
    Julie Toro Wood
    November 1, 2018 at 10:23 am

    If your jeans are too loose at the bottom and you want to roll them, try the 80’s fold – fold the hem over itself, (almost like you are pleating it) and then roll it up. We did this with all of our jeans back in the day over our hightop Reeboks (I am so dating myself, lol).

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