Fall/Winter Fashion

Stripes + Kick Flares for Fall

Happy Tuesday, friends! I hope you’ve all recovered from Monday. Today I’m styling kick flares for fall.

This is one of those outfits that works in theory, but I’m not sure the execution worked out quite the way I’d hoped. I mean, it’s not awful, but I can’t imagine actually wearing this anywhere. You’ll have to weigh in and let me know what you think.

Kick Flares for Fall with Madewell Thompson Pocket Pullover Sweater in Rainbow Stripe and Sam Edelman Laurna Mules

We all know that kick flares are trending, and I’m always the first to say that not everyone should embrace every trend; but there’s something casual and cool and fun about this silhouette that I like, so I keep trying to figure out how to make them work for this 47-year old mom bod.

You may remember that I styled kick flares for summer back in June, and I actually liked that look, so I decided to try styling kick flares for fall.

Kick Flares for Fall with Madewell Thompson Pocket Pullover Sweater in Rainbow Stripe and Sam Edelman Laurna Mules

These jeans are the same BlankNYC Varick that I had in white. I like the fit and the wash okay, and the 25″ inseam is perfect for me. I styled these kick flares for fall by pairing them with this striped pullover sweater in a gorgeous array of fall hues.

I really like this sweater — it’s soft and cozy with a relaxed fit and split sides. The oversized pocket is placed in a way that doesn’t add visual bulk, and the ribbed fabric is forgiving

Madewell Thompson Pocket Pullover Sweater in Rainbow Stripe

If left untucked with crop pants, it would throw off my proportions and cut me right in half, so I did a trendy front-tuck to create a more pleasing balance.

The trick with front-tucking sweaters is, they’re bulky already, so you have to tuck it in far enough that it’s not ballooning out and adding visual weight.

Kick Flares for Fall with Madewell Thompson Pocket Pullover Sweater in Rainbow Stripe and Sam Edelman Laurna Mules

It works out well with cropped pants because you need to shorten the upper body to create that 1/3 to 2/3 outfit ratio.

I could have probably used a belt, but I don’t mind the exposed button on the jeans either.

Kick Flares for Fall with Madewell Thompson Pocket Pullover Sweater in Rainbow Stripe

For shoes, I went with neutral loafer mules that blend into my skin, thus elongating the line of the leg for a slimmer silhouette. The pinkish-taupe shade also coordinates nicely with the lighter stripes in the sweater.

Like I said, it all works in theory, but I can’t help but feel a little try-hard.

What do you say? Yay or nay to the kick flares for fall with this striped sweater and loafer mules???

Outfit Details:

stripe sweater // kick flares // loafer mules // tote // earrings

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photos: Alison Cornell

Join the Conversation

110 thoughts on “Stripes + Kick Flares for Fall

  1. I just want to say thank-you, Jo-Lynne for this post. As you said, this outfit should work, but you’re not sure you’re crazy about it. It would have been easy for you to toss this post, but you didn’t. I think this is a good example of using the rules and then deciding, often by trial and error, what works for us personally. I like the look of the kick-flare style! I do think it’s going to be harder to style than skinnies, but I think skinnies are safe (and still my go-to) and this jean style is fun.

  2. I hate criticizing anyone’s outfits, but you asked 🙂

    While I am not a fan of the frayed hem, I think the jeans would look great with a more fitted top and maybe a cardigan over that. I also think the sweater would look better with skinnier jeans but not a fan of the front pocket on the sweater…

  3. I’d love for you to share more with us about why this outfit doesn’t work on you, in your mind.  I love the sweater and would like to find an all cotton similar one for less $$.  Even with the front tuck, there is still a lot of bulkiness in the mid section, which seems to be too much with the flared leg jeans.  I had a very hard time styling the flared leg jeans I had, so I got rid of them.  The mules look great!  Enjoy your day!

  4. Hi JoLynne,
    I love all the pieces but not together. Suggest a more form fitting top with the flare… which I do like on you. But the sweater looks very bulky in the pics along with making your shoulders more broad. I think the sweater would look awesome with your AG skinny jeans! 


  5. Not fond of the sweater or the jeans, they are too short. I am 5’8″ and have not really embraced short jeans. Guess I don’t like them cause it was all I could buy in the 80’s. No one designed jeans for tall women back then.

  6. I am going to go against the masses and say I like it!

    HOWEVER, the fact that you asked and voiced your concern shows that it’s not a good look for you since you don’t feel your best in it. I know society is all about looking your thinnest and wearing the absolute most flattering outfits at all times but I’m not always into that. Wear what you love, even if it’s not the most flattering outfit. Be comfy in your clothes! 

    Thank you for being brave and showing us lots of different styles and trends! You are such an asset to us all because of your willingness to do that! 🙂 

  7. Hi! I’m going to join in with the masses. I think the top is too bulky with the jeans and imo, it makes you look bigger than you are. The mules might add to the problem, maybe go with a bootie or shoe with a heel. Thank you, Jo-Lynne, for all that you do. Even if you think something is off with this look, you still showed it to us. Makes us think about how to style or not to style our outfits.

  8. I’m undecided…………. I love the sweater, but am wondering if boots would have looked better than the mules. But I understand the reasoning behind the mules. Maybe runners? I’m obviously more stuck on the footwear than the jeans and sweater! 🙂

  9. I have to agree with the others. You are too pretty for this outfit. I don’t love stripes on you – I am built similar- short waisted and have a chest and do not do stripes for that reason, it bulks us. I think the kick flares are also not a fave trend. Maybe on some people but not loving what I am seeing on most anyone for most part. I’d nix the kick flares for sure. If you like stripes do with a skinny jean to balance and add some height like a heeled bootie, but again not a fave of mine. But am sure you know all this as you have great style and love reading your blogs!!!

  10. You look really cute in these kick flares. I kinda want to try some, but I think it’s going to be hard to find the right length. I’m not a true petite, but I’m definitely not a regular either. LOL

  11. Thanks so much Jo-Lynne for being brave and showing us different styles! I am not a fan of the bloggers who just show pictures of the clothes and do not actually style them themselves. You always let us know what you think works and doesn’t work and why. That helps me so much in determining what actually looks best on me. And yes I think you look great in this style!  

  12. Wow, it’s 11am EST and you already have over 60 comments on your outfit! Here’s my take! I love the jeans, so edgy and comfortable/casual. But would also wear a closer fitting top, like one of your thinner, V-neck t’s and then a topper of some sort if it’s cooler out. Would love to see the jeans paired with a bootie that covers your whole ankle/lower leg.

  13. I think the outfit is cute.  I’d do different shoes though.   And maybe try a more fitted top with a Jean jacket  also for a different look.   Just not liking the shoes in this outfit.  Such a pretty sweater.   You’ll figure it out.  🙂.  But  I like you in this.  It’s a change right?   

  14. You always hit the target on what works and especially what looks good on you, but your instincts are right about this as I concur with others that this combo doesn’t work. And it’s very helpful to see the misses now and then! I think the sweater would look better with a longer jean and loafer or ankle boot due to both the pronounced stripes, colors, and heaviness.

  15. Good morning.. I just got can’t on board with the kick flares. I don’t think it looks good.. Mules I have never tried I wonder if they would fly off my feet when walking? I like my heel secured I guess. The sweater I would try for fall. I love that it’s soft….

    Thank you for all you do.

  16. I love the kick flares and sweater but not together. I have kick flares which I wore to Church on Sunday. I also wore a small heel with mine. 

  17. Normally, I would keep my opinion on this outfit to myself and just click off but…you asked. I don’t like anything about this outfit. The drop shoulders and wide bands are the wrong silhouette on you. They make your top half look wider. The bottoms are just too distressed. The knees are bagging and the wash makes them look old. All the threads hanging down adds to that destroyed look. Sorry, JoLynne!  

  18. I think the jeans might look better with boots. I’m not so sure about this style and length either, but Kudos to you for trying!! 🙂

  19. Hi Jo-Lynne, Well you said it in your comments – it looks like you are trying too hard. A tend is just that – temporary usually. I know for a fact if I purchased a flare jean, I would wear them once, and then once more to make sure I didn’t like them, and then off they go either in the back of the closet or to donation. My legs are long and thin so I think they would look ok but ok is just not good enough, right? When you modeled the white flares with the cute pink v neck top, it was a winner. Love your blog and love your styling advice and love the fact that you are brave enough to show us even the less amazing looks.

  20. Nay, but this has nothing to do with the model, the sweater, or the colors. I think the sweater looks wonderful on you! I don’t think kick flares look good on ANYONE no matter how long and skinny their legs are. The cigarette leg pants are a good choice to get away from skinnies.

  21. Since you asked… I believe you need one needs a more fitted top. I wore a pair with a front tucked t-shirt with a cardigan. I think your sweater adds too much bulk and the stripes aren’t great with this look.

  22. I personally don’t like kick flares. After looking through all your pictures though I realized I prefer this outfit on you in the second picture but last one not so much because the pants appear too flared and the sweater seems more bulky. Thanks for showing us new trends.

  23. All the pieces are cute individually, and the colors work well together.  I think the stripes on the seater are too large. It drapes nicely, so it must be the size of the stripes. 

  24. Hi there! You always do look so great in everything you show us! One of the things I like best about this type of post is that you teach us how to analyze an entire look by considering each feature: knit, stripes, cut of the sweater, wash, hem, waist of jeans, reasons for choice of style and color of shoes….It helps me remember all those things when shopping for myself! Thank you for all you do for us!! 

  25. Ok now I’m going to plead with you to style the kick flares with some slim higher booties (a few inches above the ankle). When I wear my kick flares with those it changes the whole look. It goes from frumpy worth flats to really pretty and flattering. A slim fitting sweater and I bet it will look amazing. You are scaring ( lol) all your readers about kick flares and I think you should  show them how cute they can be. 

  26. Reading so many outfit tweaks/suggestions, I would love to see you do another post, styling a few followers recommendations. I haven’t tried kick flares but if/when I do I will go with a dark wash. Overall this outfit reminds me of when I go camping but with tennis shoes or hiking boots.

  27. i don’t care for the Kick Flares look and would not be doing this trend. I have very long legs and the 25″ inseam would hit me just below the knee. This trend is not for me.

  28. I like the flares! Very updated and trendy. I live in California and they are popular here so maybe my eye has already adjusted. I actually think that skinny jeans look dated now 😳 so I appreciate you trying some new silhouettes. Sweater seems too bulky to me. But I like everything else.

  29. LOVE crop flared jeans …. personally I am over the skinny jean trend. This outfit though, I think the sweater is killing the look. A more fitted top/sweater would look better……maybe a knotted graphic T….. and for those wondering about these jeans for winter, I live in Ohio and wore them all last winter with loafer (if no snow) OR ankle boots. 

  30. I have to say NAY….sorry, but I just don’t think the kick flare flatters your figure and I don’t think the sweater does either. I think the way the pink stripe falls on the arm, it makes you look wider.  I don’t mean this to be negative….you asked. LOL 🙂  I really like you in skinnies and more fitted sweaters. More slimming and your style.  However….I do like the mules and bag. 🙂

  31. I’ve only read a few of the comments but agree with some in that I like both pieces but maybe not together.  🤷🏼‍♀️ Maybe something a little more fitted.  A fitted tee and a cardigan might be okay as someone else mentioned. But the length of the cardigan would have to hit just the right spot, I think, so that could be tricky too. And just why is it so hard for women??? Men just put on a pair of pants and a shirt and they’re done!  None of this proportion stuff, looking frumpy, shoes, purse, blah, blah. 😂😂😂😂

  32. It’s the shoes! The shoes, the shoes, the shoes!!! I stared at the pix, and I really love the outfit until I see your feet. I think it’s that you’ve got an oversized sweater, pants that take up more visual “room” with the flare, and a very large bag, all in fair proportion….then little, flat, nude shoes. You were trying to elongate your leg line, but I think with this outfit the shoes are overly subtle, and your feet just disappear as if you were standing in a hole. If you were wearing a neutral (not necessarily nude) wedge, platform, or even a platform sneaker of some sort–something with some heft and similar visual impact to the other visually strong pieces–I think you’d be pleased. I really like it from the ankles up, and think you look really good!

  33. Thanks for styling this look.  I enjoyed reading your thoughts and learning from others in the comments below. I won’t be trying this trend but will be eager to see what you come up with in the future because I’m certain you will find a way to make it work for you. 

  34. Nay on the mules. This outfit need needs a shoe with a heel…maybe a mule with a heel. Different question: can we wear rose jeans in the Fall or was that just a Spring trend?

    1. You can if you style them with heavier knits, darker colors, etc. I did pack mine away, though. Mine are really light colored, and I just don’t find myself reaching for them this time of year. They’d probably be cute with a chunky ivory sweater, though, and light grey loafers or booties… or snakeskin? It depends on their weight, I guess. Mine are just very light colored and lightweight.

  35. I really like the jeans. I think it’s the sweater that throwing the outfit off. I love stripes, but not necessarily this sweater. It seems that the boxiness of the sweater, plus the stripes plus, plus the short flare of the jeans just isn’t working together. Just my two cents. 

  36. I think what I don’t like about the outfit is the kick flare. When I cover up the bottom part of the jeans, I like the rest of the outfit. I like the slightly oversized fit of the sweater and it looks perfect with the medium wash of the jeans. It’s a cool, casual looking outfit. But then I see the cropped kick flare and I’m just not a fan. I suspect when my eye finally adjusts, the trend will be over, lol.

  37. I liked the outfit.  It seems something I would wear, without the front tuck I think it pulls the persons eye to that area. This to me looks more on the casual side than dressy.  And then I got to the shoes,I hate mules they make feet look extremely wide and big, especially if you have narrow feet lie I do, mules are not your friend.  I agree with others that your converse or something like that would work better. These shoes look out of place, not sure if it is the color, the fit, or just the style itself.   I have seen you style these shoes before and to me they just are not flattering on you.  

  38. I’m with the nay sayers…..and you always look fabulous JoLynne! The sweater is too bulky and I don’t care for the front tuck with so much bulk, makes you look big and frumpy. Not a fan of the jeans either and I have never liked mules. I just think they cut off the foot too much and look awkward. I think a slimmer sweater with the jeans and a wedge heel or cute flats would be much better. Thank you for always showing us so many looks and trends we might not otherwise see. You are so insightful! And thanks for asking what people think!!

  39. I’m a little late to the conversation but was curious about this post due to your comments from today.  I like the kick flares and think it’s a really fun silhouette to wear. I like the sweater too. I really think the sweater is not working with the jeans. You can definitely wear both but not together. The sweater throws my eye straight to the dark stripe at the top of the jeans instead of drawing the eye up. And then, I see the shoes.  I hope that helps in some way. 

    Keep up the good work 😊

  40. I don’t care for the choice of shoes and sweater. Try kick flares with black sock boots and a black mock ribbed fitted sweater that just meets the waste of the jeans. A body suit might work too. The top must be narrower at the waste than the jeans. Caramel and burnt orange would look great too. Kind of 70’s, cool chick vibe.

  41. The frayed hems are throwing it off, as it looks too young and sloppy for us 40 and up gals, plus the stripped sweater is too big and a nice solid colour like burnt orange, and a cute closed toe wedge, with a brown purse would have taken it to another level for fall.  

  42. I love kick flares and I think they’re cute on you, but not with that sweater or those shoes. I think a slim-fit T and a cute pair of Birks or sneaks would fit the look better! 🙂

  43. Hi.  First, I wasn’t to tell you that I love your blog. You seem to be very personable and real😊 I think the outfit you are wearing would look very cute with the sweater untucked and with a pair of sneakers. Maybe you could try it and show us if you like it. Also, I’ve noticed that several times, you’ve mentioned that you are short-waisted. I’ve noticed you are because of some of the fits of your tops. Have you ever tried petite sizes for tops and possibly for dresses. It made all the difference when I tried them. My tops don’t look too long, and I don’t have extra fabric in the small of my back.  And, no more boxiness. Just a suggestion. I wear a size 6 and weigh 124 pounds and have a larger bust. A petite small works every time😊

    1. Hi Donna, thank you! I have tried petites and they’re always about an inch too short, especially in the arms. How tall are you? I’m 5’5″ with long arms. I really am right in between petite and regular sizes.

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