Fall/Winter Fashion
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How to Wear Ankle Boots with Straight Leg Jeans

Hi friends! I’m back with more denim and shoe pairings today. We’ve talked about what shoes to wear with flares, and how to wear straight leg jeans with loafers and flats, and today I’m playing around with straight leg jeans and ankle boots.

I’m also planning a post that attempts to sum it all up with an infographic cuz I’m geeky like that! But seriously, it isn’t that hard. It just looks like it when I try on a gazillion different options.

First, let’s review the terms. Straight-leg jeans hang straight up and down the entire leg from hip to hem. They be relaxed and slouchy, or sleek and slim-fit; and they come in crop, ankle, and full lengths.

Straight-leg jeans hang straight up and down the entire leg from hip to hem. They be relaxed and slouchy, or sleek and slim-fit; and they come in crop, ankle, and full lengths.

SIZING NOTES: I’m 5’5″ and I usually wear a small in tops, a 28 or 29 in jeans, and a size 8 shoe. Gifted items are indicated by c/o; everything else I purchased myself.

How to Wear Ankle Boots with Straight Leg Jeans

When wearing a pair of straight leg jeans and ankle boots, you really only have two choices.

You can wear the jeans so the hem of your jeans ends above the shaft of the boot, in which case you will show some skin or show your socks. (If you choose to show your socks, it should look intentional. They can match the jeans or the shoes or be a contrasting color.)

The other option is to wear the jeans over the top of the boots. In both of these cases, it takes some trial and error to find the right denim + boot combo because you have to account for the length and width of the jeans, as well as the height and width of the boot shaft.

Option #1: Hem Above the Top of the Boot

The only way to make this happen is 1) wear jeans that are shorter than the boots, or b) cuff the jeans so the bottom of your jeans is above the tops of your boots.

similar jeans // Marc Fisher Alva Boots in Cloud Suede (size 8; similar for less) // similar thermal top (Rust Spice)

These straight crop jeans work perfectly with these ankle boots. The jeans have a 26 1/2″ inseam with a 13″ leg opening, and the boot height is 4″.

Or you can wear a lower shaft bootie and show a little more skin above the shaft. I’m actually not such a fan of this look because that style of bootie with the dip in the front looks dated to me, but these are gorgeous boots, and I can’t part with them. I might end up wearing them with longer straight and flare leg jeans.

Frame Le High Straight Ankle in Bosworth (28) // rag & bone Margot Bootie // Madewell Mayfair Cardigan (S)

Here’s an example of  is a look that almost works, but not quite. In this case, the 4″ shaft of the pointed toe boot just meets the hem of the jeans, and the jeans get hung up on the tab in the back.

These jeans have a 27″ inseam with a 14.5″ leg opening, and that half inch makes a big difference with these boots.

I can either cuff them, cut them shorter, or wear them with lower shaft ankle booties.

Frame Le High Straight Ankle in Bosworth (28) // Marc Fisher Alva Boots (8) // LOFT tee (S)

The same is true for these longer straight leg jeans and a similar pair of pointy toe ankle boots with a 4″ shaft. These jeans have a 29″ inseam with a 13″ leg opening, and I can pull them down over the Chelsea boots, which looks good…

But, if I sit down and stand up again, this is what happens.

AG Mari in 10 Years Highline (28) // Marc Fisher Alva (8) // Madewell Mayfair Cardigan (S)

The solution here is to cuff or cut or wear ankle boots with a taller shaft and allow the jeans to extend over the boot.

I didn’t want to cut them, so I did a double cuff to bring them up above the shaft of the ankle boots.

AG Mari in 10 Years Highline (28) // Marc Fisher Annabel (8) // Madewell Mayfair Cardigan (S)

I can’t say I’m a fan. For one, it looks dated to me, and I also don’t care for how it chops up the leg. My preference in this case is to wear boots with a higher shaft… which makes the perfect segue.

Option #2: Hem Over The Boot

Spoiler Alert: This is my preferred way to wear ankle boots with straight leg jeans this fall.

These are the same jeans with a 29″ inseam, but these leather boots have a 6″ shaft rather than a 4″ shaft, so the jeans extend over top. This high shaft works much better, even though the jeans are quite slim. A wider leg opening would look better, though.

AG Mari in 15 Years Shoreline (28) // Sam Edelman Agnes Western Boots (8) // Madewell Mayfair Cardigan (S)

It’s a lot easier to wear straight ankle jeans over top of higher shaft booties than to try to wear straight crop jeans with lower shaft booties because you always run the risk of bunching. You also have more flexibility with inseam length, and I also think this silhouette looks more current. And bonus, you don’t have to worry about freezing your legs!

It’s a lot easier to wear straight ankle jeans over top of higher shaft booties than to try to wear straight crop jeans with lower shaft booties.

Frame Le High Ankle Straight Leg Jeans (29) // Aquatalia Brigitte (8.5) // Madewell sweater (S)

These jeans have a 27″ inseam with a 14″ leg opening, and they work just fine over a boot with a 6″ shaft, such as the Aquatalia Brigitte (above) or the Sam Edelman Western Boots (below).

Frame Le High Ankle Straight Leg Jeans (29) // Sam Edelman Agnes Western Boots (8) // Madewell sweater (S)

The Aquatalia boots also look great with the longer AG Mari. I can see myself wearing that pairing a lot this fall.

AG Mari in 15 Years Shoreline (28) // Aquatalia Brigitte Booties (8.5) / Madewell Sweater (S)

While I was on a roll, I also tried these boots with the Mother Dazzler. These jeans have a 27 1/2″ inseam with a 13″ leg opening.

They’re so slim, they’re almost skinnies, but they work fine over these boots because the shaft is pretty narrow. In fact, they’re almost a sock boot. (Sock booties have super slim shafts, often with a bit of stretch so they fit very close to the ankle.)

Mother The Dazzler Raw Hem Ankle Jeans (29) // Aquatalia Brigitte (8.5) // Madewell sweater (S)

As you can see, pairing straight leg jeans and ankle boots is all about finding the right combination of inseam and boot shaft.

Pairing straight leg jeans and ankle boots is all about finding the right combination of inseam and boot shaft.

Full length straight leg jeans make it super easy because they’re long enough to cover almost any boot shaft.

These are the AGOLDE Lana Vintage Straight Jeans, and they’re a true straight style of jeans. They have a 31″ inseam and a 16″ leg opening, and they’re more of a rigid vintage denim. They fit easily over the Sam Edelman western boot with the 3″ heels.

AGOLDE Lana Vintage Straight Jeans (28) // Sam Edelman Agnes Western Boots (8) // Madewell Mayfair Cardigan (S)

And here they are with the Aquatalia Brigitte, a more casual type of ankle boots.

AGOLDE Lana Vintage Straight Jeans (size 28) // Aquatalia Brigitte (8.5)

Finally, these are the NYDJ Marilyn, with a 32″ inseam and 16″ leg opening, so they’re a little longer than the AGOLDE Lana. These are very soft and stretchy, so a great option for those of you who don’t care for rigid denim.

And because they’re so long, you can easily wear them over lower shaft booties as well. These booties have a 4″ shaft with the little dip in the front, much like the black rag & bone booties at the beginning of the post.

 NYDJ Marilyn Straight Leg Jeans (6) // Marc Fisher Annabel (8)

To sum it up: I know everyone says they’re struggling with straight leg jeans this fall, but I actually think they’re just as easy to pair with ankle boots as skinny jeans are, and even easier if you consider that you can wear socks and they won’t show. We just have to get used to wearing them down over the top of tall ankle boots, rather than above shorter shaft styles.

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57 thoughts on “How to Wear Ankle Boots with Straight Leg Jeans

  1. Thank you for all your helpful tips styling jeans this season!! Do you have recommendations for socks if you want to intentionally show them?

  2. THANK YOU for the series on what shoe/boot goes with which jeans! So helpful! And this morning I was looking at a pair of full-length gray straight-leg jeans that I have had for years, wondering if I should cut them. I think I will wait and experiment with the length as-is first.

    I haven’t yet switched out my summer for winter wardrobe yet. I’m thinking I will do shoes today and the rest this weekend. I love fall and boots are my favorite type of footwear!

  3. What a great post so us ladies can determine what to buy. Thanks, however, my budget does not allow me to spend $120 – $250 on a pair of jeans. Would love to see a post on Target or Amazon jean options that are more reasonably priced.

  4. You do a wonderful job of keeping up with current trends. I, myself, being more than 20 years older than you have seen more trends come and go than you. Sometimes, I think that manufacturers are hood-winking us. Styles change to keep us buying and sometimes they also change to save on manufacturing costs. The current trend of unfinished, cropped hems is a good example. I think the cropped hems shorten the look of our legs. I don’t find it a good look on anyone. But, the cropped length saves money for the manufacturer and so does not putting in a hem!

    The jeans you showed that are full length and brush the tops of your booties look so nice to my eye. Your legs look a mile long. I much prefer that look to any of the cropped styles. At nearly 68 i figure i can pass on certain styles that are not my cup of tea and wait a day or so, ha, ha, until the styles change to something I consider more flattering.

    I wonder if i am in the minority when it comes to passing on cropped jeans styles?

    1. I agree about the cropped jeans. I’m 5’2” so cropped jeans make my legs even shorter. Fortunately for me I can buy cropped and they’re full length on me. I wear my jeans over my boots which is way more flattering on me!

    2. 62 years old here and I am wearing the cropped with booties. Proportionally, I have long legs for my 5’4” frame so I don’t feel the look chops the line much. I really like wearing the crop with my lug soled boots and a flannel shirt or cardigan. That’s my fall mainstay outfit this year.

  5. This is so helpful! I appreciate all your comments. It motivated me to go through my own closet and just try things. It’s been a while sense I have been in jeans. I will make a wish list from that. Another take away for me is for me to take a picture of what works so in the morning when I am hurrying to get dressed I have a visual reminder! Your pictures have inspired me as the successes and failures pictures both learning tools. Thanks for posting all and walking us through that!

  6. Great post! Thank you for showing so many different options in lengths, brands and styles of denim. You do the work for us! Almost all my boots are low-heeled and I wish so many didn’t have the pesky “tab” on the back.

  7. I wore cropped denim this summer with fashion sneakers or sandals but will wear full length straight jeans with my booties. To my eye it looks better. And, this post confirmed that.
    Thank you for doing these in depth posts. It must take a lot of time. We appreciate you!

  8. I struggle with most the boots are too high heel or the light color boots get jean dye on them if I wear them over the boots. In another couple weeks here in the NW, we will be having rain and so suede is not practical and so this season I really stopped myself from buying the lighter, suede booties. You have such good options in jeans and booties to work with. I’m retired at home, so trying to figure out booties that I will actually wear for casual and not be running around in high heels. I got excited about the lower heel Brigitte Luxe bootie you posted, but wow…..$495 is a lot. LOL I’ll keep looking. I really appreciate this post and the hard work you put into it. It really is trial and error and trying to get the right combo jeans and booties in our closets. Let us know if you know of any shoe protector that protects against Jean dye on the booties.

      1. Thanks Bonnie……I’ll check Tom’s out. I do have a black heel (wedge) Tom bootie I like and is comfy. The wedge may be a little dated, but I still like them. 🙂

    1. I have had great success buying booties on Zulily.com (variety of brands & price points) most are returnable and another great option, at least for me is Amazon try before you buy, you can pick up to 6 pairs out, try them, pay and keep what you like, send the rest back no charge, I did this over the summer with sandals

    2. Yeah, I know, Kathy… I got those Aquatalia boots when they were 40% off during the #NSale. I did hate to use those as an example b/c the price is out of range for many, but hopefully you get the idea how they can look with a lower heel. They are also waterproof suede. That is just about the only kind I buy. Blondo also does waterproof suede at a lower price point.

      1. I figured you got them on sale. 🙂 They are sooooo cute and good heel height. You look great in all the jean styles and booties. 🙂 Thanks for your hard work on your blog. It really is quality. So much information with pictures to help and great writing.

  9. It’s funny how a year or more ago I would have thought the longer look on jeans was boring and the cropped look was of the moment. Now I’ve gotten use to seeing the longer length and it feels more right. I bought 2 pair of suede boots with a thin (close to the leg) and higher shaft at Nordstrom several years back and they seem to be getting me through all of these transitions. Thanks for all the info that keeps us on trend!

    1. Isn’t it interesting how our eyes adjust? We were just talking about that in Nashville, how even the slim straight leg jeans are starting to look like skinnies to me now. It’s so funny.

      1. Yes, they do look like skinnies, I have to really look! I need to get some of the new styles. I know I won’t look good in any of the wider leg styles. I am going to try to find a pair of straight leg blue jeans and call it a day!

  10. I know I’m getting a bit ahead here, but I’m anxious to see how to style these new styles of jeans with true winter boots. Since I’m looking into buying denim *now*, it makes sense that I’m thinking ahead to winter. I just can’t see any way that winter boots are going to look good with ANYTHING but skinny! Help!!! (I’m thinking Sorel, North Face, etc)

    1. MMASC……I have been thinking the same thing. I want to buy more jeans, but I see Winter boots needed and I don’t know how those are going to work either. I have been trying to remember what I use to do back in the day with the longer jeans and can’t. LOL 🙂 Like you said with the Sorel or N. Face boots. I’m sure Jo-Lynne will cover this well. It again will be trial and error with trying it and getting the right combo’s in our closet. Skinnies were sooo easy.

  11. Looking forward when this latest round of trending passes. Dresses with ruffles and tiers, sweaters with puffs either high or low on the sleeves, and $200 plus jeans that appear worn out and are ill fitting takes the fun out of shopping for me. I love how I feel when I am well dressed in classic styles remembering the rule of thirds.

    1. Straight leg jeans are SO much easier! I’m in Texas, so boot-cut never went anywhere and that’s how I’m used to wearing jeans. Now let’s discuss the “boot cut” jeans that aren’t big enough to go over the cowgirl boots! Those drive me bonkers!

      1. Ooops! I was trying to say that I just opt out of the styles that don’t suit me. Like the dresses that don’t show my waist (or put it way too high). So, basically all the dresses right now except the wraps.
        Rule of 1/3 is pretty important to a short girl with short legs!

    2. Then you should wear classic styles and create the rule of thirds! 🙂 We should all sit out the trends that don’t work for us, while keeping an open mind to evolving styles and silhouettes.

  12. This may be a fashion sin, but I cut off the tab on the back my boots… so no more catching them on the hem of my jeans. Problem solved!

  13. Great post! It’s nice to have so many options. My boots and jeans are waiting for the weather to turn! We’ve had a nice September here in the NW. On a side note, I ordered the floral Loft tee that you are wearing in this post, last week when you told us about 50% off and free shipping. I’d been eyeing it since you posted it and the sale clinched it. Ha ha.

    1. Linda….I did just what you did. I bought the floral LOFT tee on the same sale and I just received it and love it. I too was holding off. As for jeans and boots, I live in the NW too and our Sept. has been wonderful, so not much need yet for boots for sure. Just got some rain today but suppose to get nice again.

  14. Straight leg jeans are SO much easier! I’m in Texas, so boot-cut never went anywhere and that’s how I’m used to wearing jeans. Now let’s discuss the “boot cut” jeans that aren’t big enough to go over the cowgirl boots! Those drive me bonkers!

  15. Love the look of the AGOlDE Lana Jean. Love the NYDJ Marilyn as well. Others not so .much. My struggle is I can’t wear a heel. Need flat booties!
    Thanks for your time.

    1. I have the same issue!! I’ve got knee problems and feel best when I wear flats. At least Jolynne’s blog gives us some guidance!

  16. I just want to say thank you so much for your guidance on jeans and shoes/boots. I’ve worn nothing but skinnies for the past few years and just bought a couple pair of straight leg jeans. I always felt a little frumpy in straight leg jeans, but with your helpful tips on shoes, I’m so much more aware of what works and what doesn’t, and I feel more pulled together!!

  17. Love your tips..
    I have been having a huge problem.have booties o love but having problem finding jeans to wear with them. I do not like narrow legs with them at all so looking for boot cut with just enough flare to go over them. It’s a huge problem. You didn’t mention boot cut jeans…what is your advice?

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