I Tried: High-Rise, Cropped Flares (Part 2)



If you are new here (hi and welcome!) you’re gonna need a little backstory for this one.  Last fall, I posted this outfit (or see below pic).  They were high-rise, cropped flare jeans –  posted to an overwhelming chorus of BOOOOO.  (If you click over, be sure to read Terri’s comment – it’s hysterical and perfectly sums up all the others.)

But there were a few things that bugged me (and many things that bugged our readers) about the original post.  Namely:

1.  The jeans were too big.  Not only was the length debatable (I’m only 5’2″, so even “cropped” jeans need to be hemmed), but the jean was also slouchy through the thigh.

2.  My styling may have been too casual to give these jeans a fair shake.  Whenever a truly new silhouette comes out, it always takes time for our eyes and hearts and minds to adjust.  If you think back, most new silhouettes start out a bit dressy (or at least paired with high heels).  In the original article, I paired the mom jeans with a basic tee and flats.  It was a tough sell.

(Also not helping?  My hair.  Whatever.)



Round 2:  Be Fancier

So.  For Round 2, I first tried styling the original, too-big jean with heels and cashmere (I swear this combo fixes just about anything).    Just to see if this particular pair of jeans could be saved.


Heels do make it better, right?



But even heels can’t fix the fact that these jeans still skew a bit mumsy – especially from the side.  Not only are they still too long (even with heels), but – and this is worse – after a couple of wears, they are even looser through the thigh and butt.  These are not my mom jeans.  Not even worth hemming them shorter.




Round 3: New Jeans, With Heels


top (on sale!) |  jeans | shoes

Rag and Bone jeans are known for being super tight in the legs -which is exactly what I need.  So when I saw that they came out with a pair of high-rise, cropped flares (with a distressed hem – my fav), I jumped.  Learning from my previous mistakes, I first tried them on with a silky little top and heels.  There’s something about the high-rise waist that makes me feel so freaking sexy, and the bum is a zillion times better than the old pair.

There’s something about this definite flare shape – tight legs, large flare – that skews more 70’s fab (in a modern way) than mom jean (despite the extra-long zipper, haha).high-rise-cropped-flare-jeans





The problem, however, is that these cropped jeans still aren’t cropped ENOUGH.  I can get away with it in heels, but the truth comes out in flats.  Which brings me to….


Round 4: Same New Jeans, With Flats




I like the styling here – the long / short always helps (long trench, short jeans).  But it’s not enough to hide the fact that my cropped jeans are too long.  I prefer them above the ankle bone, otherwise it ends up looking like I had an accident with the scissors.





Round 5: Same Jeans, CROPPED MORE

I took these jeans back to Nordstroms and asked them to tailor them, preserving that cool, distressed hem.  There was much consternation about how well they could do this, realistically, but I held firm: Crop. Them.  My plan B was to hack with scissors, all in the name of “research,” so….fine.  It would be fine.

Nordstrom actually tailored them to perfection!!  Yay!!

But then I went and did this (BOOOO):


topjeansshoes | jacketbackpack | bracelet

It’s like I’m incapable of taking my own advice.  What was the FIRST THING I mentioned?  The First Thing?  It was to STAY AWAY from cotton and casual shoes! GAH, S!!  GET IT TOGETHER!

But we took the pics, so I will continue this torture:




Now here’s the most maddening one:


I may actually like the longer length better???  Or maybe I’m just so annoyed by my own styling that I can’t see which one is actually the most flattering?  IDK.

But since I’ve already invested SO MUCH FREAKING TIME on this trend….I’m going to continue in this bullheaded vein.  Which brings me to….


Round 5:  The Newly Cropped Crop Jeans, WITH HEELS


topjeansshoes | backpack

I THINK I’VE DONE IT.  Only 9 months, a few trips to the tailor, and a mere $$$ down, but I DID IT!  A legitimately cute way to wear to wear high-rise cropped jeans!!!




topjeansshoes | backpack


So all we need to do, in summary, is wear these jeans with pretty, silky tops, and the highest-heeled shoes we can find!! Simple!!! [S chokes on her own sarcasm]

I’d say that I’ll try to find a more mom-friendly version of this outfit, but I NEED A BREAK FROM THESE JEANS.  Not included in all of this nonsense was my brief foray into high-rise straight leg jeans and NO.  That’s a topic for another day.  Annoyingly, a few years ago I chopped off a pair of bootcut jeans and I still think that might be the way to go.

But we did get one good thing out of all of this nonsense.  Pics like this:


Sometimes I just can’t help myself.

Yay, Mom Jeans.



ps.  Gang, if any of you figure out the cropped-flare-and-comfy-shoes combo, PLEASE LET US ALL KNOW.  I need a fresh dose of inspiration.  I may eventually get around to giving it another go (and if so, it’ll be on my insta, @shanachristine), but for now, my cropped flares and I are on a break.  I suspect they’re the Ross to my Rachel, and we’ll end up back together, but ONLY TIME WILL TELL.

Shop It

For the two of you who are actually all over this trend, here’s a quick botique of the pieces I’m wearing, as well as a few other high-rise cropped flares that caught my eye.  I keep wondering if a slight tweak in cut (cause there is allll kinds of variation) would make these jeans work with flats???


  1. The camisole top looks great! But..question – do you wear that with a bra or… ? After kids, I find my appetite for a strapless bra is pretty much zero.

    • I wear it with mostly with a strapless bra, OR one of those lacy Cosabella bralettes. The straps are wide on the shoulder – they hit exactly where the tank top strap hits, so it works.

    • I honestly love this trend.. wasn’t sure at first but tried on a pair for fun at express. They were on sale so I figured what the heck. With a cute blouse and open toed booties I loved it! Just something different which I’m all about. And I agree that last one you nailed it. It’s tough with a casual shoe. But loved it with the white blouse and black wedge. ??

  2. Ok I’m sorry but I’m just going to say it: You are too cool and edgy for this high-rise cropped flair business. You just are.

    • I disagree! I think high-rise cropped flairs are cool and edgy. I can’t pull them off because I’m not cool or edgy. To be more mom friendly I would say comfy clogs?

  3. No. Cropped jeans make legs look stumpy. With heels makes it look like you stole them from a 10 year old. With long jacket: combo stumpy legs and stolen small pants. Just no.

  4. Nope. It should not take this much work and convincing (both of yourself and your readers) to make something work. I think fashion should be something you immediately love, then put it on and love even more. Otherwise? It’s just too much consumerism and not worth the cost.

  5. Love the high heel and cropped flare combo you finally got to but still not sold on the top and belt…..I think the crop flare still has so much potential, but I’m a denim lover and want every possible cut and wash to be an option! I’m leaning toward a thinner belt and sheer-ish, thin tank or sweater. I just got a pair on suuuuuuper clearance from Banana Republic and I swear I’m going to make them work.

    • I also have the Banana Republic pair (sale but not clearance….have had for a month or so)…..and, I am loving them! I think they are not as high waisted, which might help. I am more successful with a bit of a dressed up look; but I have pulled them off at son’s baseball game with platform tevas for a sporty casual look. I promise, they will work!

      • I wore them today after taking an inch off the length so they’re above the ankle bone and LOVE! IDK why everyone hates these but I agree the mid rise of the BR is probably helping make them a little less matronly. Thanks for the denim encouragement hahaha

  6. Lol, I love that you are willing to laugh at yourself and share questionable fashion picks (and pics) with us. Thanks for being such an awesome style guru/guinea pig. : )

  7. The high rise I can get behind… But the cropped thing is just terrible. It looks like you had a sudden growth spurt after you got dressed

  8. Love this article. If nothing else it liberates us all from truly bad fashion trends. I think it’s time to put the flare-crops jeans in the donation pile. They just aren’t flattering. period.

  9. Nope nope nope. Still not flattering. And you look good in just about everything so that’s saying a lot. Agree with someone above who says you shouldn’t have to try so hard and spend so much just to make a trend (and a questionable one at that) work for you.

  10. Huge props for trying and for having a sense of humor about it! It strongly reminds me of a kid who has outgrown their jeans though. It also reminds me of the old movie Oliver. Remember that? I haven’t seen it in years and years but rounds 5 and 6 made it pop into my mind. If you google images from the movie, it’s the way the little boys’ pants are cropped.

    Also, I really like round 2 with the black cashmere. I liked it back when you originally posted it too. It reminds me of a good trusty pair of broken in 501s.

  11. I love how everyone’s like, “I love you, but….” And, I totally agree. If these jeans make YOU look like your hips permanently widened in childbirth and just waited to show themselves until you put on these particular pants, lord knows what they’ll do to those of us who actually HAVE hips! Gah!

    • I thought the same thing!!! Shaina would look good in a burlap bag but some of us aren’t so fortunate. I can’t imagine this trend working for me at all. Gah!

  12. Ugh. I agree with everyone else. You are tiny and they make you look much heavier though the hips…. Just not flattering!

  13. As a super-tall girl, jeans can be this short on me when they’re not supposed to be and it practically gives me hives! I vote crop them further…into shorts.

  14. Nope. I didn’t hate the last outfit. But I think that had more to do with those amazing shoes than anything else. I think I would like a potato sack paired with those shoes! I really like both of the belts you’re wearing, but no info on those? Can you tell me where I can find them?

  15. You look good in just about anything. I think even the original too big cropped jeans looked cute on you. The trick with cropped jeans is to show some skin I think, ankle, shoulder…which is why they are trickier in the colder months. I did like the sock boots with them which gave the same shilouet as showing some ankle. Just my two cents. Thank you for all the time and effort on this post. That was some serious research and as always excellent work. Thank you!

  16. I chopped off a pair of old slim-straight jeans into cropped almost-flares and I wear them happily with flats. BUT, they aren’t high-rise and the length is pretty short, 24″ (I’m 5’2″ with short legs, usually wear skinnies at 28-29″).

    I’d like to see your new shorter cropped flares with the delicate ballet flats from earlier pics – I think that would work better than chunky vans, even keeping the same casual cotton top.

    • I did something similar with an old pair of Levi’s. Cropped them right above the ankle and they’ve frayed beautifully. I’ve worn them with perforated gold ballet flats and that works well. I have a fun pair of coral heels they’d look good with too but I may also try them with a nude sandal and see how that looks.

    • I actually wore them today with a graphic tee and delicate sandals – kind of the same vibe you are talking about. And you were right – it’s WAY better. (Will throw a pic on Instagram soon)

  17. One of my favorite articles. I love that even you (who looks amazingly put together all the time) struggles with fashion…and is someone who will try the same piece on every day hoping “maybe today” will be the day it will click.
    Love love love this read. Thanks for sharing!

    • I agree. This post is probably one of the top ten most useful posts on this site. I feel so at-sea with dressing my actual self, I like having a run-down of things to try when I know my outfit needs some sort of help.

      • Thank you for this!! I almost didn’t publish because I wasn’t sure if anyone would care! Glad to know this helps…..

  18. Can I just say I’m in love with your hair in round #5?!! So amazing. And the top, GAH, I love it so!!!! And I don’t mind the jeans……but I really think they need a more elegant heel…..pointy toe pumps or thin strappy heels…….but yay for not just writing this trend off!!!

  19. I have a pair of high rise crop flares from Citizens and I love them. I am 5’2″ as well but Ari have bigger legs than you. I have worn them with big tall platform sandals, Frye boots, and Gizeh Birkenstocks and loved them with all. I really love these jeans. I have them on now actually. I haven’t figured out the perfect top… But I have a tank with a cut in sort of arm hole, don’t know how to describe – I think it comes closest to working the best with the jeans, and when it’s colder I wear a plain looser thin knit sweater. Not sure, but I get a lot of compliments on the jeans.

  20. Yes on round 5 but it seems like a LOT of work for one look and zero versatility. At least you are getting people talking… #silverlining

  21. Just no. The jeans look like you’re a kid who just had a growth spurt. If they weren’t cropped, they’d probably look really cute on you. The problem is, though, that they would make my hips looks wide just because I’m a size 6.

  22. OK, I like #3 and #5. But since the looks seems to be dependent on heels, and since I can’t wear heels…. I am going to have to leave this trend alone. I DO want a pair of full length flares though – what shoes for those?

    But, no, no, no to the momjeans!

  23. If I were forced to choose, I’d go with the Rag and Bone jeans pre-alteration. Theoretically, the shorter look should have worked but somehow I think cropping some of the flair out didn’t work. I actually like the R&B with the flats. But. I have to agree with almost everyone that a pair of jeans/fashion trend shouldn’t take this much work. I’ve also seen the cropped flairs in other fabrics on other women and…it’s not a good look, in general. (And I agree you look sensational in almost everything so the fact these don’t work is saying something!)
    Now, what I do like is the army jacket which I’m coveting. The Nordstrom price is $500 CDN and that’s way out of my price range. Any suggestions for other jackets at a more affordable price point? (I’ve been searching but can’t seem to find the perfect one.)

    • I know, that jacket is annoying. Topshop will get one in – almost exactly like it – from time to time, but it tends to sell out immediately. But that’s the first place I’d start stalking. If I find any others, I’ll let you know.

  24. Oh I think that looks 3 and 5 look great on you! However, my eye gets hung up on the big thick belts. Cropped high rise flares are too fashion forward for me to try any time soon, but I love being exposed to the new look! And I really love that you posted the other pics for us to laugh at. It makes you still ONE OF US. Thank you! 🙂

  25. This is meant in the nicest possible way. You know that friend that everyone has, or had at some point that dated this cool guy that was a total loser, but she kept trying with him saying “you just don’t see his fun, tender, loving side”. Everyone else can see that he isn’t worth her time……

  26. Oh man, I loved the last look! I love cropped pants, and I see them as totally different than capris. I have bad feet so I always wear comfort shoes, so I have to skip some trends that require heels. I just chopped all my straight leg jeans that had been resting for a year in my drawers and now I’m getting tons of wear out of them. I think they are cool and edgy and honestly I’m a bit surprised so many of you are calling them mom jeans. I guess yes if you mean cool hip moms. I know everyone doesn’t have money to jump on trends, or wants to- but I think Shana had with the new jeans, cropped shorter, and with heals/platforms.

    • Yeah, I’m with you on the cropped jean thing – very cool and edgy. I’ve been hacking away at all of my skinnies and straight legs – it’s just these darn flares that are giving me trouble. And babe, if you ever want to send in pics for a little inspiration – especially since it sounds like you’ve got this look on lock – we’d love to feature you….

  27. Have you tried a lacy, embroidered tunic/peasant top? I hacked a pair of stovepipe jeans a couple of years ago (cut them on a bias – it was hippy-edgy), and love them with platform wedges (like #5) and a colorful embroidered tunic in the summer.

  28. Maybe it’s my age, but I hate those jeans. However, I LOVE you and love the fashion math going on in this series. More fails, please! They are too funny and interesting. (And maybe it’s our turn to post pictures! lol)

  29. Having the same dilemma. Just took a chance o a Madewell pair. Love their jeans usually, but can’t decide on these. They are super comfy though…the mom jeans are calling! Eek!

  30. Ok. So after putting these in the hard no category, my daughter (14) asked for these for Christmas and I laughed. Out loud. Mostly because I remember you saying sometimes us “older people” embrace trends last. So I bought them and she hated them BUT I LOVED them. I’m not super but pretty leggy. I think that helps. I wore them with the FP Cecile ankle boots anD it works well. I also tried the FP bandals (boot/sandals) this summer with a silk tank and belt. A tiny tuck defines the waist and keeps the silhouette slim. Said 14 yr old loves the on me- she’s taller but my legs are still longer. Maybe Cam can try a few looks just to see if that may be the issue? Personally I really like the final product. Thanks for being honest on the effort that it took to get it right, way to keep it real. Lol.

  31. THANK YOU FOR THIS POST. I have the same rag & bone cropped flares and I looooove them – such soft denim with the perfect amount of stretch. I have been literally agonizing over wether to cut them more – and I’m 5’5″! Now it’s confirmed that they are best left alone.

    I think these are quite versatile and look great with the vans, flats, and wedges. What’s throwing me off about these looks on you is the full tuck with the clunky belt, it’s a little jarring. I wear mine with slightly slouchy v or scoop neck tees, half tuck, no belt.

    • Ok. So I tried them with the half tuck today, and it was SO much better. Even with flats – so thank you!!! (I’ll post to Instagram….eventually….)

  32. I think these jeans work best when they don’t look like they took too much effort to style. Either pair them with some cool Golden goose sneakers and a cute tee or else with a pair of Maryam Nassir Zadeh sandals and a dainty top. I agree with a previous commenter that the big belt and wedges are too much for these jeans.

    • I tried them today with a graphic tee (half tucked) and my go-to Minkoff sandals. I actually loved it, so thank you for this. Effortless is always best. (At least for me.)

  33. I’m not really sure this works for anyone. You, it doesn’t work because you are short. Me, it doesn’t work because I’m too tall. Goldilocks problems.

  34. I think this is a problem of proportion, quite honestly. Us shorties can’t do the dramatic flare in this silhouette–these jeans are cut with a much taller frame in mind. Have you tried the j.crew Billie? They’re a much narrower flare (esp. after i took 3/4″ off) and the barely-there kick is kind of a cool Mia Wallace look.

    • I second K on this – Shana, your chopped bootcuts might be similar to the Billie’s, with a narrower flare, and might work.

      I also think the problem is that the kick flares here break too high, because they make them for taller women. I have to ask: is it worth it?

      • No, I looked again – they don’t break too high. Maybe the flare is just too flared, like K said? Anyway, Shana, you are a stunner and always look terrific. These aren’t terrible by any means, but you don’t look easy in them.

  35. Shana – You always inspire me. Take a look at Banana Republic Medium Washed Cropped Jean. They nailed the look. Looks like the length is shorter than the ones you wore.

  36. I remember writing that initial comment and feeling very satisfied with myself, like it really came from the heart. The difference between those shitty jeans from the first post and these jeans is laughable- it’s barely the same trend. Needless to say, I like Round 3 the best and if when we finally meet you were wearing that outfit, I’d offer up piggy back rides wherever we went. Oh my gosh, If you could only see me right now, I’m like 15 months pregnant, the idea of that is so, so, so absurd. XO!!

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