Straight Ankle Jeans Two Ways

In Saturday’s try-on post, I shared three pairs of straight ankle jeans that I recently ordered, and this pair was by far the favorite. Bonus, they’re 30% off right now!

I’m still #teamskinnyjeans all the way, but I know you guys want to see some other styles, so I’m giving these straight ankle jeans a shot today.

There was some debate in the comments as to whether the straight ankle style looks better with loafers and ballet flats or worn over higher shaft ankle boots, so I’ve been taking notice of how they’re being worn on various websites and blogs, I’m going to say they can work with both.

In fact, I took it a step further, and I’m showing them both ways in this post — with my favorite black suede loafer mules for casual wear, and with red leather block heel ankle boots for a dressier look.

I styled these booties a few weeks ago with bootcut jeans, and I do love the subtle peek of red from under the denim, but it’s a shame to over up these gorgeous boots with long pants.

Cropped jeans are the perfect solution, and the straight ankle style is right on trend this fall.

Since these boots have a higher shaft, they work well with straight ankle jeans because the jeans fall nicely over the top of the boots.

AG Prima Ankle Straight Jeans straight ankle jeans with Vince Camuto Thelmin Booties

It does create a rather boxy look, though, which some of you aren’t crazy about. Maybe a sock bootie with a skinnier shaft would work better.

For reference, I usually wear an 8 in Vince Camuto boots, but I sized up to an 8-1/2 in these. I think because of the pointed toe, I needed a bit more room.

The shaft is also kind of stiff, so I have to wear socks. I like these bamboo rib crew socks because they’re moisture wicking and super soft. They’re thin enough to fit in all styles of boots, but not so thin that they don’t provide any warmth, and they stay put all day long.

Jo-Lynne Shane styling dark wash AG Prima Ankle Straight Jeans straight ankle jeans two ways -- with loafer mules and red block heel booties.

This sweater was one of my top sellers last season, so I was excited when Nordstrom brought it back this year. The sizes and color options are dwindling, but it’s still available in a few combinations. I also have it in the black because it’s such a great closet basic. Aren’t the ribbed details so pretty?

While the website says it runs big, I’m wearing my usual small, and I believe the fit is just right. I wouldn’t recommend sizing down from your normal size in the Caslon brand.

Because I’m a plain Jane, I don’t usually wear this sweater with a necklace; but to jazz it up a bit for these pictures, I wore this double ring pendant from Kohl’s. When I do wear a pendant over a sweater with a cowl or turtleneck, I think it looks best when the pendant is extra long, and extends past the chest area so it doesn’t compete with the neckline.

Caslon Cozy Rib Detail Relaxed Turtleneck

For a more casual look and one I’d probably get more wear out of, I tried the same sweater and jeans with my black suede loafer mules. I love these shoes, but you’ll want to size down half if you’re ordering.

A lot of you said you prefer the straight ankle style with loafers and flats because it leaves the ankle area visible, and I’m definitely seeing a lot of girls wearing the straight ankle jeans with this style of shoe, but this look isn’t very practical for colder weather.

I’m also wondering if this look works better with lighter wash jeans because there’s less contrast between the color of the jeans and one’s skin.

Jo-Lynne Shane styling dark wash AG Prima Ankle Straight Jeans straight ankle jeans two ways -- with loafer mules and red block heel booties.

I don’t know. The jury is still out… I want to like these jeans; I just don’t know if I quite nailed the look.

It could also be that the top isn’t right for them. Because the jeans are cropped, I think I need a shorter top to balance out the proportions. I guess this is why we’re seeing a shift to shorter tops!

On the one hand, I’m tempted to say that if I have to work that hard, I’m just going to keep reaching for my skinnies because they’re a lot easier to throw on and go with most of the tops and shoes in my closet. On the other hand, I suppose that’s how our style gets stuck in a particular decade, so I’m going to keep trying.

Every time the pant trends shift, we have to pivot and figure out the tops and shoes that work best with them. In a few years, this will probably all seem so obvious and effortless, but for now, I’m still trying to figure it out.

Jo-Lynne Shane styling dark wash AG Prima Ankle Straight Jeans straight ankle jeans two ways -- with loafer mules and red block heel booties.

sweater // jeans // mules // booties // bag // necklace // hoops // photo credit: Alison Cornell

What say you? Are you embracing this trend or taking a pass?

Be sure to visit Cyndi and see the winter outfit she’s styling today!

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62 thoughts on “Straight Ankle Jeans Two Ways

  1.  I appreciate that you try new trends, but also appreciate that you like what you like and know what works well on you and are willing to stick with it. By the way, I had commented that I bought the same loft utility pants but wasn’t sure about the leg opening, so I had them taken in at the bottom to make them more like skinny jeans, and it turned out great!

  2. I’m definitely a fan of the boot look! It makes you look long and lean and the flats just don’t… I know we all have to wear flats sometimes, but I have the same problem when I wear them, I feel frumpy… not that you look frumpy…..maybe I’m just doing something wrong! But my vote is for the boots!

  3. I’m not a fan of this style jeans, but you made a valiant effort. I think they just look too short, and agree that showing that much foot/ankle skin when it’s cold out is impractical.  Love the sweater though. Maybe straight leg jeans with a little flare, that are longer. 

  4. It took me forever to get on “team skinny jean”! Now, I am more comfortable in them than the straight leg look. I may be the last member to retire from the team. HA! The few pair of straighter legged jeans I have picked up, I tend to like with flats, but more of a point toe style. Not trying to promote the brands or style, but I have the M Gemi Stellato, and on me, find that to be a good style. There are many other brands doing that same “look”. Everlane also has a nice point toe shoe. I have the mentioned shape of shoe in a navy pair, a dark gray, and also deep tan.. A little less contrast than a black shoe. I am not professing to have all the answers, just putting some ideas out there.

    I must say this PA weather is the pits!! I keep saying 2018 was the year without a summer.

  5. First of all I love the split screen idea. Great way to show comparisons. This was the straight style I picked from your try on… I would be ok with either but I’d probably go with a lighter wash with a mule or loafer so yeah the leg doesn’t stand out so much. But at the end of the day this style jean just seems like a lot of work especially this time of year so I’ll stick to my skinnies.  I think maybe it’s done easier in spring and summer when you can wear that style jean with a nice wedge and cute top. Well enjoy your day it sounds exciting for your son. I remember that day with our son and daughter when they were of age. We have a milder rainy day today too after a cool crisp day yesterday.  Weather still up and down but hey no snow.

  6. I think you nailed it! These straight leg jeans are the best I’ve seen you style. They seem similar to my beloved AG stevie fit from Anthropologie. I agree, they are harder to match a shoe with but both the loafers and boots look great. I’m pear shaped so I jumped on straight leg jeans and cropped flares a long time ago since skinnies aren’t the best on me and I’ve found that front tucking usually works well if the shirt is too long. (Though front tucking sweaters is hit or miss as far as not looking silly.) In the winter I wear supergas or slip on sneakers with them a lot. Also lower shaft booties. They look great with your boots though so I’ll have to try them that way, too!

    1. Hey Nikki, thanks for the comment about pear shaped ladies wearing this trend. I have seen this comment a few places and it is definitely enough to get me into the store and try them on. I have a hard time with jeans, so any style that is on trend and will fit my “bootie” is a winner! 🙂

      1. Good luck!! I find that the ones that are slim fitting through the thighs work best. The more relaxed fits still don’t work for me.

  7. I love the crop straight pants with the loafers vs. the booties. And I agree with your comment about how they may not be practical for the cooler weather……and since here in Ohio we went from summer right into winter I didn’t have much time to wear my straight (or my flare) crops. Weather can really cramp our fashion choices 🙂

  8. Jo-Lynne, 
    These outfits both look great! BUT you gotta like it ! HA. What if you wore the straight jeans with a more fitted shorter top? Sort of like when we ( I) used to wear a flare and would need a more fitted top so it did not all look boxy? Maybe that cute top and vest or one of your V neck sweaters that fit close to the body? I sure don’t know just wondering. Thank you for all the great info. I am going with Old Navy on this trend and keep it economical as it is not yet for me a investment type piece. Enjoy your son being around! 

  9. I’m a fan of full length straight leg jeans, but the cropped/ankle ones just look like they ate too short.  The dark wash of yours helps.  However,  I’m not sure why people work so hard to make unflattering looks work just because they are “on trend”

    1. I’m not convinced the look is unflattering — I like it on others. So I’m trying to figure out how to make it work, and if I can make it work for me. If not, I’ll happily pass. I’m always the first to say not every trend is for everyone. But I liked this outfit, so I don’t think the straight ankle jeans are totally a lost cause: https://jolynneshane.com/how-to-wear-straight-cropped-jeans-this-fall.html

      And as you know, part of why I do these posts is because people ask me to style new trends, so it’s not all about what works for me. 🙂

      1. I would love to see a side by side comparison of the same outfit but swapping the straight crops for straight full length 

      2. I like the other outfit better too. I can’t decide if it’s the shorter sweater or the lighter wash? I think I’ll keep my straights long, like my boot cuts. I appreciate you trying everything out for us and then putting yourself out there for us to pick apart! 🙂

      3. I just popped back to the other post where you styled cropped straight leg jeans. I think that outfit worked because your sweater was cropped too. We might all get on this trend! 

  10. I like it! I think it just takes a little getting use to seeing yourself with bigger ( not skin tight like skinny jeans) on the bottom and and more fitted on top. I struggle myself ! Being a 34 DDD and size 6 jeans , I feel awkward and larger when in reality I look more balanced in this type of jean. Thanks for your post!

    1. Yeah, 34G here, lol. I feel like it works in theory, but not necessarily in practice. But you’re right – sometimes we have to give the eye a chance to adjust to new styles. Which also goes back to Heather’s question. I used to think skinnies were unflattering, ha!

  11. Love the look with boots, maybe a grey loafer would work better less contrast to your skin.
    Northeast weather is the pits this year…Waiting for Spring!
    Already voted here in New Jersey! Have a great day!!!!

  12. I would hv to say …I would pass
    Being taller than you it looks like the pants shrunk
    Even with cute boots!
    As always you make it look cute with flats and boots.
    Enjoy your son …saw mine this past weekend …
    Warms mothers ♥️ to see our boys/men!

  13. I’m glad that you have reasons to get dressed and get out of the house today!  Oh, I heard yesterday that there’s new research showing that people who put up their Christmas decorations early are happier people.  Just sayin! 🎄 Personally, I like straight leg jeans because they don’t wrinkle up in the legs and stay that way upon any movement.  With your red boots, I am wondering if they fall over the top of the boots when you change from a sitting position to standing.  I do like my skinny jeans, but they aren’t my favorite, and I don’t know that I have a favorite.  The weather here is way too warm for Nov!  We could have storms today, but our chance of severe weather is a 1 out of 5.  Our granddaughter voted for the first time, as well, and was super excited.  Enjoy the time with David.  Christmas break will be here before you know it, so he’ll be home for a bit.  Make extra effort to smile today – that will make you feel better!

  14. Well the plus side is that you keep trying to embrace the trends no matter the struggle – bravo! 😊 And you definitely connect with your readers which is why you have so many followers. (Not many bloggers ask the audience’s opinion.) 

    I still prefer a more fitted top and flat shoes with the straight cropped jeans, but then again I’m in CA and the weather is so mild I don’t have to worry about getting cold ankles. 👖👚☀️ 

    1. I just wanted to jump back on here because I went to LOFT this afternoon to return a few items I’d ordered online and found out they CHANGED their return policy…. 30 Days or NO RETURN allowed! I was 2 Days past the 30 days so I couldn’t return anything…..and the items don’t fit!! Oh I was so mad! I don’t think I can shop there anymore because 30 days just isn’t enough time for working people to always get back to the store. Ugh! I guess I’ll be donating brand new items to charity. 

      Any-who…. I just thought you might like to know  and share that with your readers as I know a lot of us have been LOFT shoppers. 

      1. Yes, someone brought that to my attention last week. That’s no good at all. I will really have to be careful b/c I often am lax about making my returns. I got caught with 3 brand new with tags tops from White House Black Market b/c they wouldn’t take them back – and they allow 45 days, I think. Usually I found if the tags were on, and things were still on the sale floor, they would give some grace with those return policies, but LOFT must really be cracking down if they didn’t even allow you to return in store. I assume they offered store credit? For me, that would be fine b/c I order stuff all the time, but for a lot of people, I realize they wouldn’t want that. I’m with you. That policy stinks. And also that they charge for returns – that always sticks in my craw. LOL!

        1. I love that you get it! (The frustration 😣)
          Yes, they offered me store credit but at the current selling price (even with tags on and the receipt). One top was half of what I paid for it do I just couldn’t do it. So I kept two tops and a necklace (plan to use the necklace as a gift) and will donate the tops. My church always has a Christmas gift donation tree so I’ll give the tops to them. 
          I still like LOFT clothing and sales, butvwill have to definitely think carefully before buying next time and/or mark the calendar with a reminder of when I bought it! 

  15. Thank you for stepping out of your comfort zone to style looks that you are on the fence about for yourself, but might help others decide if the look is for them. I’m not sure about this trend either, based on my body type, but I think I like them styled with the bootie better. I agree that perhaps the sock booties that are out there might look good too. Thank you for what you do. I’ve been following you since this past spring, and you’ve encouraged me to try different things that I wouldn’t have thought to do otherwise. I wish I found you sooner!

  16. I’m going to join in and complain about the weather. We are dreary and hot! Yuck! That means no cute sweaters and all the suede has to stay home….no fun at all! Right now it’s so foggy I can’t see the building next door.

  17. I’m struggling to find a cropped straight jean I like as well. I’ve tried on a lot. But they never feel quite right. I’m going to keep trying though!

  18. Jo-Lynne, I totally appreciate you trying the trends so it’s not 24/7 skinnies, but this cropped straight trend is just for the birds.  I don’t find it cute on anyone, and this is WAY too much work.  Maybe just straight pants, period, but the cropped thing looks horrible.  Those Loft dress pants you styled a few days ago though, THOSE were gorgeous on you!  And the bootcuts you’ve styled previously look great.  

    Do you have any full-length straight jeans to try, not cropped?  The shoes/booties thing is a huge conundrum, too.  I have a large bootie/shootie wardrobe, and I’m not interested in investing hundreds of dollars on slightly-tweaked heels and shafts to wear these cropped abominations of jeans, LOL.

    Color me cheap, but I can’t justify new shoes for this Twilight Zone trend.  Maybe in warmer climates they’d work with espadrilles or something, but the mules and flats look off.

    Thank you for trying though, and those red boots are gorgeous!

  19. Well at first glance I thought I liked them better with the booties, but now I’m confused. They both look good and I’m thinking I need to hunt out some of straight cuts and give them a whirl.

  20. Thanks for sharing. I am getting ready to buy some straight leg jeans, so this was helpful. I really like the look with those beautiful red boots. I think you nailed that one. Enjoy time with your son today. Next year I will be in your shoes with my daughter!

  21. I prefer them styled with the red booties. I don’t know about the slides. As you said, it could be that contrasting expanse of white skin showing that knocks the look off. I thought the look with the flats made you look frumpy #sorry.  
    I bought some straight leg jeans (black/indigo) but not cropped. Like you, I just can’t master this trend, so I’ll pass. 

  22. Jolynne, I have the banana republic slim straight jeans in blue and black and I love them. I’m 5’5” and the hit my ankle at a perfect spot and I think they look less boxy then a pure straight jean.

  23. But overthinking is my spiritual gift! It’s my duty to use it to its fullest potential. Haha!

    I agree, it seems like it should be that simple… and maybe I just need to allow my eye time to adjust, but I just don’t like how they chop off the leg in a straight line before the leg actually ends. At least when skinnies are cropped, they follow the natural line of the leg.

  24. I think those jeans look awesome! I have been reading your blog for awhile now, and maybe have never commented, but I like both ways you styled them. Love the darker color and the cropped length–to me it looks very fashion forward. Just FYI–I have a pair that are straight leg, lighter wash and full length and i have to say they look a littlle “mom jeans” sometimes, depending on the shoes I wear. So I agree, they can be difficult to pull off!

  25. I must say I like the red boots much better with this look. Can’t really pinpoint why other than my eye likes it! That is all. Carry on!;)

  26. The straight leg jeans with flats or mules works for us in south Texas because for the most part, it just isn’t cold in the winter! I am passing on the trend styled as you did with the red booties. IMO it looks silly, as if the pants were just too short…. I can’t get behind the booties trend with skinnies, either. I have booties but I wear them with my boot cut jeans. I think I look like I am teetering on heels when I wear booties with skinnies. I am large busted, so maybe that contributes to the out-of-balance look when I attempt it! I need something more substantial on the bottom half to make me look more balanced overall. I have some straight leg jeans, and I wear them longer, at the length for boot cut. The shorter jeans cut off my leg; I am only 5’3″ and need all the length I can get!

  27. Hi! I have a full length pair of straight leg jeans from Loft and have worn them once with flats, but something felt “off.” I have short legs, so maybe that was it – too stumpy? Maybe they need to be cropped when worn with flats? Not sure what to do with these jeans. I guess over the top of boots is the only option – or hem them to cropped? Roll them up (but then I feel like that looks like I’m ready to go for a walk on the beach). Ugh. :0(

    1. Hm, it’s hard to tuck them into boots, they usually get bunchy. Altering could help, but be sure you like the cropped look on you. Maybe fold them under to figure out the length you like best.

  28. I appreciate you trying to be on trend, but I feel like I’m just not seeing these straight leg jeans in the Midwest yet. The crop nature of them seems weird too, come snowy weather. I can’t get on board at all…..not sure who they would flatter. Team skinny jeans here.

  29. I bought a pair of straight leg jeans from Nordstrom’s recently (Articles of Society). They are full length and I feel they are too long on me – I can’t quite figure out how to style them. My booties look kind of bulky underneath the legs, but I don’t know if I should cuff the legs to the top of the bootie? They look okay with flats but it will soon be too cold to do that. I think the cropped straight looks good on you, Jo-Lynne!

  30. I’m Team Red Boots all the way.  I think the line of the leg looks  better – and you get to see those awesome boots.  I agree the flat loafer look is less pleasing.  I think it’s because of exactly what you mentioned – the dark jeans and dark shoes are too much of contrast to bare skin in the middle, so the leg line is interrupted by that.  

    Great post with showing both styles – cheers!

  31. I think both these looks are your best attempt to make these jeans work so far! I really like them with the red boots. The pic from the side of you walking in the boots could be a magazine ad…so stylish! But I’m still feeling pretty meh about straight cropped jeans in general. I haven’t been doing skinnies for nearly as long as you have and they still feel on trend for me. Plus I live in a place that is likely years behind most trends. LOL!

    1. And I think that’s important to consider. I’m in an area that is kind of behind the trends too, but not so far that I can’t try them out here and there. I tend to follow bloggers in NYC and areas that are ahead of here, and I enjoy being a bit ahead of the trends, but I do have to wait for my eye to adjust sometimes before I can get behind some of them.

  32. Love the red boots outfit!! I think, as you mentioned in the post, that the flat shoes may look better with a lighter wash denim (or maybe a lighter colored shoe? I have straight leg denim in light and mid wash, maybe I should try similar outfits out to see what I like best. 

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