Fall Trends to Try: Flare Jeans Now & Later

Happy Friday, friends, and cheers to the weekend! Today I’m teaming up with Cyndi Spivey to style another trend for now and later, and today we’re bring flares back! Although I’m cheating a bit, as mine are technically bootcut jeans.

When I asked on Instagram if people are into flares, 75% said no, so . . .  I’m not sure how many of you even want to see me style these pants, but we’re doing it anyway!

These are the AG Angel bootcut jeans, which I found at Nordstrom last spring, although my exact wash is only on Amazon now it’s the 17 Years Ceaseless Destructed. And there’s a pair in a very similar wash (a little less distressing) on sale at Shopbop the sale ends tonight, and the code is STOCKUP19.

I sized down to the 28, which is a bit snug in the waist, but I was afraid the 29 would be too big in the thighs.

These are obviously a very casual wash, so I decided to style a more casual look with them something I’d wear for running errands, to go to my one of daughter’s band performances, or to hang out with friends on the weekend.

The issue with bootcut jeans, of course, is that they require your shoes to have a very specific heel height.

I always get my bootcut jeans hemmed to wear with heels because I think they’re most flattering that way, so that made it even harder to create a casual look, but I found these Vince Camuto Gigietta booties in my closet, and I think they’re perfect.

(There are more sizes at VinceCamuto.com, by the way. Mine are Tortilla Suede, and I recommend sizing up half.)

The Western styling makes them more casual than most of my other booties certainly more casual than pumps or my peep-toe sandals and the pointy heel helps elongate the leg, which coupled with extra length of the bootcut jeans gives you legs for days!

These booties have a 3-3/4″ heel heel, which is the height of heel I brought with me when I had my jeans hemmed. A lot of my heels are in that 3-3/4″ 4″ range, so I knew I’d have some options.

This is a comfortable heel for me, but of course you can wear lower heels with bootcut jeans and flares . . . just be sure to have them hemmed accordingly.

FIT TIP: Ideally, your flares will be 1/4″ — 1/2″ off the ground, with shoes on.

To keep the look casual, I styled these jeans with a graphic tee.

I’ve purchased a few graphic tees lately, but this one is my favorite for its wider neckline and flattering fit, and it’s a nice quality slub cotton.

I also fell in love with the NYC skyline with the red embroidered Manhattan. Living in Philly, I end up in NYC a few times a year, and I love the energy and pace of the city, so I thought the tee was fitting.

For accessories, I wore this Lucky Brand bracelet, and I meant to bring these earrings.

I love Lucky Brand jewelry with my casual outfits, and the mixed metal look is very much on trend at the moment.

I carry all handbag styles, but a tote is always my favorite, and my taupe Everlane tote coordinates nicely with the booties they don’t match, but they go. #thankyoustacyandclinton

While I don’t typically hang around the house in 4″ heels, I like this elevated casual look for ball games, kid’s events, casual coffee dates, things like that.

To take my flares into winter, I basically just swapped out the tee for a sweater.

I also changed boots to a pair that’s darker and more conducive to wearing socks, although I’ll probably wear the Gigietta booties all winter, depending on the weather.

This camo sweater is from Anthropologie, and while it’s pricier than some, the quality is really outstanding, and I love the fit and feel.

Anthro does run sales from time to time; in fact, this sweater was on sale for a few days last week, so it’s one to watch if you like it and don’t want to pay full price. (Click the “Get Sale Alert” button below the picture in the shopping widget at the end of this post to receive an email when it goes on sale.)

This bag is an oldie but goodie, and it works in well with the polished but edgy vibe of this outfit.

The price seems to fluctuate (#amazonproblems) and I paid a lot less than it is currently going for, but even if I’d paid full price, the cost per wear would be mere pennies at this point.

And don’t be shocked, but I’m wearing a belt! I really like how it completes this look.

For many years you really didn’t see a lot of women wearing belts, and now they’re everywhere. Of course, the logo belts à la Gucci are the trend du jour, but I went for one that’s a more subtle.

This O ring belt by R Minkoff is a glossy but very soft leather, and for size reference, I needed the large.

My booties are Club Monaco. I saw them on another blogger a couple of years ago and stalked them until they went on sale. They’re gorgeous, but they don’t seem to have a similar style this season, so I hunted down a few other options.

These are similar, but with a lower heel for those who want that; and these are a good option for a more budget-conscious pair. I also like this pair, and this pair looks amazing if you prefer leather. (The last two are on sale at Shopbop through end of day.)

The only other thing I’d add to this “later” outfit is my black leather jacket. Besides the extra warmth, it would make a great completer piece to this simple look.

I’m excited to see flares and bootcut jeans becoming more popular again, although I’ve yet to see the ladies in my neck of the woods wearing them. I’m still very much in skinny jean country, but I don’t see trends taking off here as early as they do in more urban areas.

I’m curious if you’re seeing a resurgence of flares and bootcut jeans where you live. I do love my skinnies, but it’s nice to have other options.

How about you? Are you ready to rock the flares?

Outfit Details:

AG Angel Bootcuts (on sale at Shopbop) // NYC tee // taupe booties // taupe tote // camo sweater // similar black sock booties (more below) // black satchel // O-ring belt // sunnies c/o Maui Jim

Be sure to visit Cyndi and see how she’s styling flares for now and later!

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photos: Alison Cornell

Join The Conversation

85 Responses

  1. I’m one of the minority who couldn’t wait to see you style flares!  So ready to pull out my bootcuts and actually be on trend!  

    1. My friends and I were astonished and upset last year where all we could find were those skinny jeans that just don’t look that great on a lot of women, especially if you are wearing plus sizes.  Bootcut jeans look so fantastic on almost everybody, more so than other styles.  Jo-Lynn Shane looks incredible in bootcut jeans!  Give the skinnies a much needed vacation!😂

      1. I agree with all of you! I might be in the minority but I don’t think the skinny jean is that flattering on most women.

  2. I love flares but always find them super tricky to style with a casual vibe. This post will really help me with that. Plus, the jeans you featured are gorgeous. Love them so much! Great job, as always. 😍

    1. If by casual, you mean flats ( shoes or booties)  as long as they have the pointed toe it works. Of course your boot cuts have to be hemmed for a flat. 

  3. You look long and lean in those jeans! Personally, skinny jeans look terrible on me although I like them, so it’s nice to see someone styling the bootcut. You should wear them more often.

  4. I love your outfits – so classy, polished and perfect for the season.
    Thank you for styling these – it’s reminded me that bootcuts are a perfect option for autumn/winter. 
    Best wishes Jane

  5. I live bootcut jeans!  Flares?  Well, it depends.  I live in an area that is growing like crazy, so many northerners moving here, but there never really seems to be an on trend style.  Most people in this area are still wearing their actual gym clothes all day or jeans and a tee.  Skinny jeans are still popular, but the high school crowd wears the super high rise.  High rise is a trend I just cannot pull off!  My bottom looks much better in low cut jeans.😬😂

    I think your second look, with the Camo sweater, is awesome!😍

  6. Great look on you & love both tops!!  I just love how you cover all the pros/cons & give recommendations as to how to wear the outfits you style.  If I found a pair of boot cuts the right length, I may give them a try!  Have a great Friday!  

  7. I am surprised that only 25% are into flares. I love the look of them…they are so flattering and elongate the legs perfectly. I love both ways you have styled them. That graphic tee is adorable and I am totally digging that camo sweater. My only problem with flare jeans is the length because once the ground gets wet here, it stays wet until summer…so I always need to wear boots over my pant legs if I don’t want to be soaked. 


  8. Awww, Jo-Lynne, you are speaking my fashion love language!  I don’t know I’d call them flairs, but bootcut is right up my alley, even down to our matching Vince booties!  (I’m doing the snakeskin ones.)

    You look amazing in skinnies, but it’s nice to see the change of styles.  These bootcut/flairs look soooo good on you!  And I love the sweater and belt with it, too.  Heck, I love the tee and boots and bag.  It’s all great!

    Two huge snakeskin-covered thumbs up from me!

  9. I think both looks are fantastic  on you!  Thanks for sharing.  I’ve seen a lot of local women in bootcut jeans.  I don’t think they are wearing them to stay current, I think some people just prefer them.  I’m glad there are more options out there these days.  

  10. Fun looks, JoLynne! Just bought a pair of bootcut jeans in a dark wash at Old Navy and they are amazingly flattering.  Like the skinny jeans but sometimes feel like they make a look a little top heavy. Glad to see bootcuts making a bit of a comeback, it’s nice to have options! 

  11. I hear ya about the flares. I was wondering the same thing when I posted about them. I think, though that some of the flares like the ones you’r wearing are much more similar to boot cut and I think it’s great to show them so people see how flattering they can be. These look great on you.

  12. Love the 2nd look with the lower rise jean and belt!! Looks great on you and I need that sweater:) What size are you wearing?

  13. I love both of these looks. So leg-lengthening and slimming. You look gorgeous! I am seeing this look more where I live (metro DC area). I recently bought a Gucci belt bc of a rare sale and I love how it pulls an outfit together and cinches in the baggier styles. The one thing I am not sure about is the longer length. I see how it lengthens the legs, but I think I prefer the cropped wide leg or flare bc I worry about tripping over the hem.

  14. Great looks on you!  I really like the one with the black accents…vey slimming. 
    I’m not seeing them in my “neck of the woods” either, but I sure wish they would make a true comeback. Why do they have to make them sooo stinking long though?  I know of very few people with a 33” inseam. 

  15. Both these looks look great on you. I can’t remember the last time I wore flares/ bootcut. I honestly don’t see many wearing them in my neck of the woods. Young or older 🤷‍♀️… seems like the straight or skinny still rules the pack here.
    Have a great weekend 

  16. You look great in both outfits! I think bootcut or flares are very slimming on most women. I love them so I’m glad they’re making a comeback! I can’t wear heels for very long so that creates a problem to some extent but I’ll definitely be wearing flares this fall and winter and also my skinnies!

  17. Love the second outfit!

     I’m in a suburb of Chicago, and mostly see skinny jeans and athleisure, and now some of the cropped straight, but I did see someone wearing bootcuts with trendy sneakers and up to date top and the outfit looked good. I’m headed to Nordstrom this afternoon to try on jeans and bootcuts are on my list to try.

  18. I can’t wait to wear my bootcut or flair leg jeans!  While I like my skinnies, I don’t like having to tug on the legs to keep them in place.  You look great in both outfits, but you are really rocking in the Anthropology top with a belt.  WOW!  The few times that I have been in a retail store, I have not paid attention to the jeans.  I stayed focused on why I was there, got in and out.  Have a fabulous day!

  19. Yes to the flares! Actually, the boot cut! I have some great ones I have saved from a few years back. I think they look sharp with a heeled bootie. I love skinny jeans too so it’s just a different look. Happy Friday!

  20. I gotta say that you look great in those boot cut jeans!  Especially with that black belt and camo sweater.  I think I want some too!

  21. I love bootcut jeans for the winter months! A dark denim is great for church with booties with a heel. They look as nice as dress pants. On casual days I wear them with a chunkier shoe or boot. Something about a chunky shoe, boot cut jeans and a thick, cozy sweater just works and feels so relaxed on a cold day!

  22. Love, love love this trend – anything that’s a little “boho” and these jeans are perfect!  They really create an amazing look and they look fab on you.  Love that camo sweater from one of my favourite stores…and the boots…perfect outfit Jo-Lynne but I’m liking the winter look more – maybe because I’m so bored of everything right now and can’t wait to do the switch up to warmer clothes…

  23. Great post! I loved both outfits, and your bootcuts look great on you! I was so looking forward to this post as I have my eye on a pair of Free People flares. I have worn my bootcut jeans several times and received many compliments. I appreciate all your efforts to switch things up and try new things! It’s fun! 

  24. I like flares. I know this pair is called bootcut, but to me they seem a little wider at the bottom than regular bootcut jeans. Love the wash on them. I still prefer skinny jeans, but these really look nice on you. I’ll have to try to see if they go on sale. 🙂 I still haven’t pulled the trigger on that sweater. I absolutely love it, but it is SO expensive! (And I already splurged on that Vince hoodie.) 🙂

  25. Ha! I’m a girl of the 70’s! I’m always ready for flares/bootcut. In fact, I really haven’t given them up over the years. I was hesitant to try straight legs, and definitely don’t do skinnies.

    1. I feel like a country song, I was bootcut and flare when bootcut and flare wasn’t cool. I have my Dad’s super tall genes so I can wear skinny jeans, but I’ve got my Uncle’s big ski feet so flat shoes and skinny jeans make me feel like a clown; a tall, skinny clown ready to stamp out forest fires. When I wear bootcut or flare jeans with wedge, heel, boot, booties or flashy statement shoes I feel like I’m walking the catwalk blowing kisses to all my fans, darlings. Read that last sentence in Zsa Zsa Gabor’s voice. Ah, the power of bootcut and flares, who knew?

  26. Love the bootcuts which seem to be a little wider than regular bootcuts!  When I buy real flares, I have to cut them down so much that they end up not looking right on my 5’4” frame!  They are usually made so long…and I am past wearing heels more than 2” anymore.  There seem to be few petite flares around.  Anyway, I love your bootcuts, great alternative to the 70’s flares, great for fall and winter. (Just don’t bring back the elephant pants..that was a wild style from the early 1970’s!)

  27. I love the bootcut jeans on you!!!  Makes you looks so tall and slim!  I was slow to get on the skinny jeans bandwagon and although I do love them now, I think bootcut is more flattering for most women.  I live in the DC suburbs and although skinny jeans have reigned supreme for the past few years, I’ve always seen women wearing bootcut.  Especially dark ones that were dressed up for casual work days. 

  28. I think my favorite thing about boot cut jeans is they’re all over thrift stores, lol. Much easier to find second hand than skinnies.

  29. Those jeans look fantastic on you! I love the sweater and just set an alert. Also, I’m loving the Jls fashion tribe on Facebook💕
    Have a great weekend.

  30. I love bootcut!! As most others have said, I believe for most women boot cut is very flattering. Skinny jeans can accentuate hips which, let’s face it, most women who have had children have, but the small flare of the boot cut I think balances the body and helps to slim us all! I live in a rural area where nobody is really into what’s “hot” and what’s “not” fashion wise which is great because we aren’t tied to that. Thank you for sharing your outfits. I love seeing them!!! This is a GREAT LOOK on you!!!

  31. Being a curvy gal, I have quite a few pairs of boot cuts (and am in fact wearing them today to work!). I LOVE that sweater and will definitely be stalking the sale. 🙂 Love both these outfits on you.

  32. I like the boot cut on you, it’s a nice change. I have a pair of boot cut jeans and although I don’t wear them as often as the skinny jeans it’s fun to change it up sometimes. Thanks for the post. 🙂

  33. Funny that yours are bootcut….I was just about to ask the difference between bootcut and flares! 🙂
    I love a bootcut! Could be b/c I love to wear cowboy boots! I’m wearing the W&W itty bitty bootcut today…but with leopard pumps b/c it’s going to be 100 degrees today. Sigh. Love the look! So much more accessible to those of us with a more “pearish” shape and big legs!

  34. Cute outfits. I like the jeans, even the light distressing is tasteful.  I love the camo sweater but not its price tag. Sigh!  It’s still a bit warm here in Chi-town but I was at the mall (an upscale large suburban mall) yesterday and saw some trendy stylin’ ladies in boot cuts. They looked sharply put together but still in the minority vs skinny jeans. Since no one was staring at them, I assume my fellow shoppers thought nothing unusual of their fashion. Then again, flares/boot cuts pretty tame when compared to some of the get-ups either in store windows or on fashion victim fellow shoppers (oh, err, trend-setting shoppers.) Thanks for always making me ponder my fashion decisions.  Have a great weekend. 

  35. I certainly agree with most of these comments, the flares look great on you with the boot. I have ONE pair that I saved from over 30 years ago, from GAP, and they are the perfect wash and softness! They are a little too “low-rise” for my comfort now, but it’s a sweet remembrance of my “youth”! HA HA!! I have bought newer versions and love wearing them with boots with a chunky heal. Also love the belt, I think it really finishes off the look when tucking in a top, not sure why they were “out of favor” for awhile. Good job, Jo-Lynne!

  36. LOVE this look on you! Very flattering! The flare jeans balance the hip and shoulders. Just my opinion but very few ladies can pull off skinny jeans and look balanced. Hope the flare or boot cut makes a big comeback in fashion. As always, thanks for your advice and willingness to show ALL fashions. God bless, Rhonda

  37. Love these looks on you! I wear bootcuts more than skinny jeans. I have some from AE that are called Skinny Kick, and are are skinny leg with a slight boot cut bottom. Those are my favorites. 

  38. You look amazing in these jeans! It’s such a flattering silhouette on you and you look taller and thinner (not that you need any help in that area;)) I still wear my bootcut because sometimes its nice to stand up and not have to adjust your pants (pull down the calf section of skinnies) eveytime  you do.  I think you style all your jeans so nicely but this is my favorite fit on you!!

  39. This was a perfect now and later post. You look great in these jeans!  I’m one who likes bootcuts.  I still love my skinnies, but it’s nice to have a choice. 

  40. I’m definitely warming up to the flare thing….especially since they’re supposed to be better for us “fuller seated” gals.   BTW, I have no sympathy for your thigh problem…🤣.    Love both looks, but all about the second one.  I love a dark top with lighter wash jeans…plus that camo.

    Is there a difference in flares and bootcut?  Kick flares are shorter, oui?  Just trying to keep up.

  41. When you asked about flare jeans on your pill I was thinking a wider “flare” so I said no. So now … I’m lost … I thought flare jeans had a wider bottom?  Am I wrong?  What’s  the difference between a flare jean and a bootcut jean?  Inquiring minds want to know.  🤔

    But I do love how you styled these.  ❤️

  42. Hello

    Bootcut all the way for me please.

    I unfortunately have hips which rather dictates the need for boot cuts or flares. Sadly under no circumstances can I wear skinny jeans – which kind of makes jean shopping rather tricky here in the UK as stores here seem rather reluctant to relinquish their skinny jeans.

    I think you look great in bootcut jeans.

  43. When I responded to the Instagram poll, I was thinking “kick flares” of which I am not a fan. However, if “flares” means boot cut, I say YES. These are so cute on you. A boot cut, or modified boot cut, is kind of universally becoming I think. However, I think it looks better in fall/winter. Todays looks are perfect! Thanks for sharing them!

  44. I love a good pair of bootcut jeans. I prefer the dark wash and black ones. I find they make us look taller & thinner. A win/win!  I don’t wear them as much as skinnies but still have them in my wardrobe for a change from skinnies. I’ve bought a few pairs of straight leg jeans as they seem to be trending. Now to get used to a change. 😜 
    I love your Camo sweater. It has cooler colours than most. Might be one to stalk! 
    I always wear a belt with jeans. I feel it finishes the look. I sometimes pick my shoes & purse after I pick my belt. Lol 

  45. I love these looks, especially the sweater and belt. I’m to the point that I really hope “style” will embrace that we all look good in different things and we don’t want to have to go buy all different tops and shoes to make things work when jeans styles change over. I’d rather buy new clothes because I want to, not because I have to. I think skinny, straight, and bootcut/flares all look current just now, and hope they all remain an option.

  46. I have been wearing the flared jeans  a long time.  I never gave them up.  Well for 2 + years I had to because if a foot  injury bug now I m beginning to wear some boots again I can bring out the flares.  I’m a 60 s child you know.   Loved the whole look.    Thanks for showing us your style.  I loved how you styled them.  Looks so cute on you 

  47. LOVE bootcut jeans. They look better on most people than skinny jeans do. Took me forever to love skinny jeans (which I do now). That being said, I’m reluctant to pull out those bootcuts because most of the population has not re-embraced them quite yet, so I feel a little too retro wearing them. Hopefully, all will soon accept fully both skinny and bootcut.

  48. Love both looks on today’s post! You look amazing! I am noticing from looking at photos on line and in magazines that boot cut jeans actually make people look slimmer than do skinny jeans. Maybe it is bc more width at the bottom balances what is on top? Not sure…..but after being long devoted to skinnies, I am realizing that I need to embrace the bootcut style!

  49. I don’t think I’ve seen any bootcut or flares around where I live which is a mid size city in the south. I only see skinny jeans and straight. I don’t really care for bootcut but I do like the cropped straight trend and the cigarette jeans you shared recently. Thank you for all the helpful advice and tips. I truly appreciate the help with figuring out what to wear.

  50. I think flares and bootcut jeans look MUCH better on most women. I wear them almost exclusively. You look great in them! I would love to see more posts including these flattering cuts!

  51. Love the flare jeans on you. Been waiting for bootcuts to make a comeback. They are really my favorite look and find them to be very comfortable.

  52. I really like the flares so I’m glad they are back in style.  Find they create a balanced and pulled together look. 
    I know I’ve told you before, but think you look best in flares.😊

  53. I finally found a pair of flare jeans I can wear with my purple cowboy boots. Can’t wait for it to get cooler in Arizona.

  54. I love flares and bootcut jeans! You look so great!! They are better for cooler weather because your ankles are covered. 😉

  55. Can you tell me what size you are wearing in the NYC graphic tee? I just love it and the reviews were mixed on the sizing. 

  56. I don’t care what your poll said, I am so glad that you styled the bootcut jeans anyway. I love bootcut jeans and they look way better on my pear shape than skinnies. Lol Would definitely love to see more. 

  57. I love flare jeans! So glad to see you styling them Jo-Lynne. I just purchased some from my recent Stitch Fix and I love them. Always have loved wearing them with heels. Whether they are on trend or not I continue to like them.

  58. I love this post! I’m very much a bootcut/flares girl (the skinny jean season for the past few years has been hell for me) so I’m excited to see this trend coming back. Please feature more outfits with flares/bootcut jeans. I love that sweater and definitely want to buy it…when it goes on sale!

  59. I know you think skinny jeans are life, but you always look AMAZING in boot cut jeans! As others have said, they are so much more flattering on most than skinnies. I hope you will continue to style these jeans. 

  60. I’m so glad that bootcut and flares are back in style. I lost 20 lbs recently and am wearing one size smaller in jeans and pants. I hit up my stash of smaller sizes and realized that the pants and jeans I saved are all flares. While I still love my skinny/ankle jeans and pants, I’m excited that my wardrobe has some versatility. What’s old is new again!

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