Fall/Winter Fashion
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What Shoes to Wear with Flares This Fall

With flares and bootcut jeans making a big comeback this fall, I’m getting tons of questions about what shoes to wear with them and what length they should be, so let’s discuss!

First, let’s define our terms. Bootcut jeans are fitted through the thighs and flare out slightly from knee to hem. Flares are basically a more exaggerated form of bootcut jeans. They fit straight through the hips and thighs and flare from knee to ankle, and leg openings are typically wider than 20″.  Both come in crop, ankle, and full length styles.

For more information, you may want to read: Women’s Pant Styles and Hem Lengths Demystified. I’ve also written about the Denim Trends for Fall 2022, where I also rounded up a bunch of flare and bootcut jeans that I like and recommend.

For the purposes of this post, I’m lumping these two styles together because they are pretty much interchangeable when it comes to pairing them with shoes.

Treasure & Bond leather bomber (S) // Halogen scoopneck sweater (S) // AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Marc Fisher 3″ booties (8.5) // AllSaints tote

Flares & Bootcuts: Shoe Pairings for Fall 2022

And one more caveat, before we get started. All of the jeans and shoes in this post were fully stocked when I was trying them on, but then Nordstrom put some of them on sale, so sizes may be picked over. There are plenty of similar styles out there, though. Just compare rise/inseam/leg opening measurements to be sure you ‘re getting the same fit, if you’re buying a similar but different pair.

SIZING NOTES: I’m 5’5″ with an hourglass shape, and I usually wear a small in tops, a 28 or 29 in jeans, and a size 8 shoe. I’ll include the sizes I’m wearing under every picture, in case that helps you shop.

Full Length Bootcut Jeans + Boots: A Sure Thing

Since bootcut jeans are literally made for wearing over boots, so I started with a sure thing — full length bootcut jeans and a pair of western-inspired booties.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Sam Edelman Agnes Western Boot (8) // Evereve ribbed tank (S)

These bootcut jeans have a 32″ inseam with a 19″ leg opening. If you’re unsure about denim measurements, I break them all down in my post, How to Shop for Jeans Online: Denim Measurements & Fabric Composition.

The boots have a 3 1/2″ heel with a narrow snip toe. Typically, a more streamlined toe looks best with flares because it visually elongates the line of the leg. For that reason, a boot with this shape in a lower heel works just as well. Just hem or cut your jeans to the desired length to go with the heel height you most typically wear.

When it comes to proper length, it used to be that we wanted our flares to come to within a half inch of the floor, but these days, with crop and ankle flares trending, it doesn’t really matter if they’re a little higher. I actually like them better when they’re more like an inch off the floor. I feel like it looks a little more modern.

So what about boots that have a rounded toe or square toe?

Next I tried the AG Farrah Boot with the Vince Kaye from the #Nsale. These boots have a streamlined silhouette with a square toe and a 2 1/2″ heel. They look fine with these jeans, but in my perfect world, the jeans would be a little shorter.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Vince Kaye 2 1/2″ Block Heel Bootie (8) // Nordstrom Signature cardigan (S)

These Mother Raw Hem Flare Jeans have a 32″ inseam with a 21″ leg opening, so they’re more of a flare. (The AG Farrah has a 19″ leg opening, making them more of a bootcut.)

These jeans are supposed to be the same length as the AG Farrah Boot, but I think they are a tad shorter, and I like this length a lot better with these boots. It’s amazing what a difference a half-inch can make.

Mother 32″ Raw Hem Flare Jeans (28) // Vince Kaye 2 1/2″ Block Heel Bootie (8) // Halogen v-neck sweater (S)

Next, I tried the Mother Raw Hem Flares with the Aquatalia Brigitte — a rounded toe bootie with a 2″ heel. I don’t mind this look, but I like these jeans best with a more pointed toe.

The dark wash reads dressy to me, which pairs better with a dressier boot. These booties with the tan suede and round toe read more casual, so I think I’ll end up wearing them with light wash jeans.

Mother 32″ Raw Hem Flare Jeans (28) // Aquatalia 2″ boots (8.5) // Nordstrom Signature sweater (S)

You can’t go wrong with dressy pointed toe boots and flares. The Marc Fisher Urmi Pointed Toe Bootie has a 3″ heel, which is perfect with the 32″ inseam on these jeans for a more elevated look.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Marc Fisher 3″ booties (8.5) // Treasure & Bond leather bomber (S) // Halogen scoopneck sweater (S) // AllSaints tote

Okay, moving on. I think we all know that bootcuts and flares look great with heeled boots.

Full Length Flares + Clogs: Another Slam Dunk

Full length flares also work really well with clogs because the platform gives you that extra height you need to offset the width of the flares, but the heel drop isn’t as extreme, so they may be more comfortable to walk in.

These Kork-Ease Darby Clogs have a 4″ heel with a 1″ platform, so the heel drop is just 3″. This pair is similar, but again, a lower heel clog would look good too. The platform gives you the addition height without needing a big heel drop.

Mother 32″ Raw Hem Flare Jeans (28) // Kork-Ease Darby Clogs (8) // BR sweater (S)

And here’s another look with a different pair of bootcut jeans. These are the Good American Good Classic Bootcut Jeans, and they have a 33″ inseam with a 19″ leg opening.

Good American bootcut jeans (6) // Kork-Ease Darby Clogs (8) // Vince cardigan (similar for less)

Full Length Flares + Sneakers: Not My Fave

I also wanted to try the Mother Raw Hem Flares with sneakers, even though I knew they’d be too long, and I can’t say I’m a fan.

Mother 32″ Raw Hem Flare Jeans (28) // rag & bone Retro Sneakers (39) // Caslon thermal top (S)

Even if I were to cut these jeans so they still extend over the top of the shoe but don’t drag on the floor, I don’t think I’d like the combination, but maybe my eyes will adjust as longer jeans continue to rise in popularity.

And my reservation could have more to do with the dressier dark wash than the length and style of denim. Without playing around with other washes, it’s hard to say for sure.

Full Length Flares + Heels: Vavavoom!

When you want to level up, full length flares look really good with pumps and dressy heels. These Michael Kors slingbacks have a 4″ heel, which I realize sounds really high, but they’re actually quite walkable. I love this look.

Mother 32″ Raw Hem Flare Jeans (28) // Michael Kors Cleo 4″ heels (8) // Ann Taylor blouse (S)

And this one too. This is my early fall date night outfit formula right here.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Michael Kors Cleo 4″ heels (8) // Theory halter sweater (S)

If you don’t wear 4″ heels, a lower heel pump or slingback can work, but a pointy toe will look best. These Marc Fisher Zala Pumps with the 2 1/2″ block heel are one of my favorites, and the pointy toe will be perfect with flares this fall and winter. I just may need to shorten a pair to wear with them.

I didn’t try these jeans on with any of my flats because they’re way too long to even get the idea. I do think they would look fine with a pointed toe flat, or even the ballet flat/Mary Jane combo that is going to be popular this season.

I may end up cutting a pair of flares or bootcut jeans to wear full length with flats, but I’m more likely to opt for a pair of ankle or crop flares. Speaking of which, let’s move on to ankle length and crop styles.

Ankle & Crop Flares + Clogs: A Match Made In Heaven

These are the Paige Claudine Raw Hem Flare Jeans, and they have a 28″ inseam (that is ankle length on me) with a 17.5″ leg opening. Here’s how they look with the same clogs as I was wearing above.

Paige Claudine 28″ Ankle Flare in Slater (28) // Kork-Ease Darby Clogs (8) // Evereve vest (S)

I love this combination because the jeans hit right above the shaft of the clog, and exposing just that hint of ankle is slimming and leg-lengthening. It seems counter-intuitive because the jeans are shorter, but I like this look every bit as much as the full length flares with these clogs.

Here’s a side-by-side, for comparison purposes. Notice how I did a front tuck with the shorter jeans, to keep the overall outfit proportions in check. (And I have no idea why my wall looks like a totally different color in each picture.)

Clogs also work with crop flares and crop bootcut jeans. These are the Citizens of Humanity Isola Cropped Bootcut Jeans, and they have a 27″ inseam with a 16 1/2″ leg opening. So far, the clogs seem like the most versatile shoe for all lengths of bootcut jeans and flares.

Citizens Isola 27″ Cropped Boot (29) // Kork-Ease Darby Clogs (8) // Evereve vest (S)

Here’s another outfit with a slightly shorter pair of jeans. These Mother The Insider Crop Step Fray Bootcut Jeans are more of a true crop, with a 26″ inseam and 15 1/2″ leg opening.

This picture is from last year, and these UGG Judi Clogs were discontinued, but it shows you how this pairing works together.

UGG Judi Clog (9) // Mother Insider 26″ Crop Step Fray Bootcut Jeans (28) // Z Supply Claire Waffle Long Sleeve Tee

I always get questions about wearing socks with clogs when it gets cold. You can certainly do that if you want, but I’m more likely to opt for booties once it gets cold out.

Oh, and also, if you want some foot coverage in your clogs, I love these sheec Clog Socks! They really do stay on your foot, and they protect your pedicure, as well as give your feet a bit of cushion and comfort. They also make these thinner nylon half socks.

Crop Flares + Platform Sandals: Yes, Please

Crop and ankle flares also work well with platform sandals, for basically the same reason as why they look good with clogs. Here I’m wearing the Paige Claudine Raw Hem Flares with my Seychelles wood heels.

Paige Claudine 28″ Ankle Flare in Slater (28) // Seychelles sandals (8) // Kut from the Kloth jacket (M)

That combination works fine, but I actually like these sandals better with a slightly shorter flare because I prefer to see some space between the strap of the sandal and the hem of the jeans.

Remember, these Citizens of Humanity Isola Cropped Bootcut Jeans have a 27″ inseam with a 16 1/2″ leg opening. That extra inch makes all the difference.

Citizens Isola 27″ Cropped Boot (29) // Seychelles sandals (8) // Evereve sweater vest (S)

And I know we’re talking about shorter lengths, but platform sandals also look great with full length flares.

Edwin Ryder 33″ Bootcut Jeans c/o (29) // Seychelles sandals (8) // Evereve top c/o (S)

Crop Flares + Boots: Depends On The Shaft

When it comes to ankle and crop flares, ankle boots are definitely an option, but you have to watch the shaft height. If it’s too low, your jeans will catch on the back of the shaft and it looks all janky.

In the pictures below, I styled the Sam Edelman Agnes Western Boot with all three lengths of flares. These work because they have a 5 3/4″ shaft. Even when I sit down and move around, my crop flares don’t get hung up on the top of boot.

Citizens Isola 27″ Cropped Boot (29) // Mother 32″ Raw Hem Flare Jeans (28) // Paige Claudine 28″ Ankle Flare in Slater (28)

Here’s an example of booties I would NOT wear with the cropped flares. These are the Marc Fisher Annabel from last year, and they have a 4″ shaft. They look fine from the front, but not so much from the back.

  Citizens Isola 27″ Cropped Boot (29) // Marc Fisher Annabel Western Booties (8) // Evereve vest (S)

That may not bother some people, but it’s a no bueno for me. These boots do, however, look amazing with full length flares. Take a look.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // Marc Fisher Annabel Western Booties (8) // Evereve vest (S)

Ankle Length Flares + Loafer Mules: Not So Much

Now, here is where it gets tricky with ankle and crop flares. The 28″ inseam on the Paige Claudine makes them ankle length on me (they may more cropped on taller women) and I love how they look with the clogs and platform sandals shown above.

They also look good with pumps and strappy block heeled sandals and booties, but all of those have a bit of a heel.

Here’s how they look with a pair of flat loafer mules. I thought this worked when I shot the outfit, but when I got the pictures back from Alison, I realized I don’t love this combo. It’s not terrible; but I definitely look shorter and squattier in the picture with the flat shoes.

I mean, I even look thinner in the picture on the right. There must be something different with the camera angle as well, but even so, the way the jeans land right on the edge of the shoe, with no skin showing, throws off the whole look.

Paige Claudine 28″ Ankle Flare in Slater (28) // Steve Madden Pointed Toe Mules (8) // Seychelles Wood Heel Platform Sandals (8) // Kut from the Kloth jacket (M)

Crop Flares + Loafer Mules: Much Better

Crop flares are a much better option. See how much better the loafer mules look with the cropped boot? Just giving the eye a place to rest (the skin at the ankle) and having less contrast between the color of the jeans and the shoes makes such a big difference.

Citizens Isola 27″ Cropped Boot (29) // Steve Madden Pointed Toe Mules (8) // Evereve sweater vest (S)

Here’s another angle of the same denim and shoe pairing. I still prefer a heel a longer, leaner silhouette, but these work for more casual days.

Citizens Isola 27″ Cropped Boot (29) // Steve Madden Pointed Toe Mules (8) // Evereve ribbed tank (S)

These jeans look even better with pointy toe flats with a lower vamp. (The vamp is the part of the shoe that covers the top of the foot. Low vamp shoes end at the top of the foot near the toes. High vamp shoes come further up your foot and possibly even up to the ankles.)

I just picked up these Sam Edelman pointed toe flats with flares and bootcut jeans in mind. I think they’ll look good with full length flares too, I just need to decide which pair of mine to cut, or find a pair with a 29″ or 30″ inseam off the rack.

I don’t necessarily like the style of those flats with the sweater vest, but I wanted to at least show the denim and shoe pairing. I would opt for a blouse or another more feminine top with these shoes.

What About Crop & Ankle Flares with Sneakers?

I have had TONS of questions about pairing flares with sneakers, so take a look.

First, I tried the Paige Claudine Ankle Flares with my Vejas. And you know what? I don’t hate this, although I do feel like the jeans hit at an awkward spot on the shoe. If they were even a half inch longer, I think they would look better.

Unfortunately, I don’t have any flares or bootcut jeans with an inseam between 28″ and 32″, so I can’t show you how full length flares would look with these sneakers, but you can probably envision how an extra inch would be perfect.

Paige Claudine 28″ Ankle Flare in Slater (28) // Veja Esplar (29) // Evereve sweater vest (S)

And of course, there is a high contrast between the black jeans and white shoes, which visually cuts off the leg at the bottom of the jeans. If the sneakers were black or dark grey — or any dark color, actually — my legs would look longer.

Alternatively, if the jeans were lighter, my legs might look longer. Look what happens when I swapped the black ankle flares for a pair of blue crop flares.

Evereve vest (S) /Citizens Isola 27″ Cropped Boot (29) // Veja Esplar (39)

As a reminder, this Citizens of Humanity Isola Cropped Boot has a 26 1/2″ inseam with a 16 1/2″ leg opening, and the Paige Claudine has a 28″ inseam with a 17.5″ leg opening.

All I did was change the color and the length of the jeans, and suddenly this outfit looks much more pleasing to the eye.

I think it’s because there isn’t as much contrast between the black jeans and white shoes, but also seeing that little bit of ankle gives the eye a place to rest. Especially because I’m wearing a short-sleeved top, having some skin at the ankle balances and opens up the look a bit.

Finally, I threw on the Citizens Isola Cropped Boot with my rag & bone Retro Sneakers. Because they’re a little bit chunkier than the Vejas, I wasn’t sure how these sneakers would work, but they’re fine.

I just prefer to see more skin at the ankle, so I changed into the Mother Insiders. They have a 26″ inseam rather than 27″, and that makes a big difference.

Mother Insider 26″ Crop Step Fray Bootcut Jeans (28) // Citizens Isola 27″ Cropped Boot (29) // rag & bone Retro Sneakers (39) // Evereve vest (S)

In Conclusion

When I get to the end of a post like this, I’m always feeling like I wish I’d tried more options, especially ones that don’t work. As if this post isn’t long enough already… I guess there are always more outfit possibilities!

Since the wider the leg, the shorter you look, high heels and platforms definitely work best with flares, but I think a case can be made for wearing flats or sneakers if the overall outfit is well balanced.

For now, I plan to keep my full length flares for heels and wear crop and ankle length styles with everything else. But you can certainly wear your flares to the floor with flats if you want to.

I’m planning to do a post like this with straight leg jeans sometime next week, so stay tuned for that!

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50 thoughts on “What Shoes to Wear with Flares This Fall

  1. Platform shoes, love them with flares.

    I have comfortable all day platforms from Naturalizer that look great with flares. I’m 5’3’ so 3.5 inches in height is ideal. Also have platform chunky sneakers that surprisingly look good with my NYDJ flares that are on the narrower side.

    Tall skinny people can look good in flares with flat shoes, not me!

  2. Great post!! – so very helpful! 🙂 Are open toe booties not longer in style? I love them for this time of year in New England but do not want to look out of date.

  3. This is my favorite type of your posts: all the explanations of why or why not things work together. I know these must be a lot of work- thank you!

  4. The timing for this post is perfect because yesterday I received a boot cut jean and a flare jean that I had ordered. I tried them on with different boots and shoes and wasn’t sure what I liked. They are full length and I now think I would prefer the ankle length for me because I like to wear the lower heel.
    I’ve been wearing ankle straight leg jeans with sandals so look forward to you showing me what to wear them with as the weather gets cooler. So much more confusing than the skinnies haha.
    Thanks for helping us

  5. Thank you for this, Jo-Lynne! It’s very helpful to see these examples on you. Yesterday I cut 1.5 inches off the Mother flares after pinning them and trying them on with some shoes. ( I am only 5’1”). I will probably do the same with the Paige. Thank you for your recommendations on both of these jeans. Very soft and comfy. As a child of the 70’s, I am excited about the boot cuts and flares. It makes it easier to stop wearing my skinnies. I am packing them away for now.

  6. Thankfully I love boots with my bootcut jeans – makes it so easy! I honestly can’t get over all the unfinished hems – I pay good money for jeans, so companies can [email protected]*$ well hem them! Maybe I’ve just become an old person now that I’m in my 40’s, ha.

    1. Snort. Yeah, well, it’s just a matter of preference. I like the raw hem, it adds some texture and looks a little more casual, which suits my style. Also makes them easier to “hem” if they’re too long. But if you like the finished hem, that is what you should buy! 🙂 It definitely looks more polished.

  7. Thanks so much for all the efforts on this post! The side-by-sides are really helpful. Maybe you can sneak some additional photos, the ones that don’t work, into other posts– you’re usually good about that 🙂

  8. Love the post and would be very interested in what to wear with straight and wide leg jeans or pants. What about espadrilles- would they work for flares? I an not a fan of clogs or mules so I stick to pointy toe boots, heels and ballet flats. Thanks!

  9. Thank you for the help with correct shoes! I saw you wearing the black SWAT FAME Kara Jacket and I was wondering if what size you purchased?

    1. I have the small, but mine is from last year. I don’t know if they’ve changed it or not, and I have gained a few pounds. I would recommend ordering 2 sizes and trying both. I did that with the brown one and ended up keeping the medium.

  10. Thank you for all of your hard work! I know I am showing my age, but I am not a fan of the raw edge or the “floods”. Thankfully, I wear dresses most of the time so I can sit this trend out. In the meantime, on the rare occasion that I wear jeans, I will be the senior lady rocking my skinny jeans and sneakers.

  11. THANK YOU! What a helpful and eye opening post. In the comparison where all you did was change shoes and your positioning when Alison took the picture, I’d love to see that comparison again, but with you standing the exact same way. It is so helpful to see the side by side pictures. I have been so used to not showing skin around my ankles/feet, I’ve got to retraining my eyes, because seeing the little bit of skin does look so much better. Have a great day!

    1. We can try but it’s almost impossible to get the exact same angle, unless we use a tripod and don’t move it while I change, haha. May be a good exercise to do here at the house, tho!

  12. Very informative! I’d be interested to see straight jeans in the mix, I have pretty much given up my skinnies but have a couple straight pairs that I still wear. Same concept? Full length with heels, etc and cropped with flats? Which length with sneakers?

  13. Hi. Thank you for another great post. Any suggestions on what to wear with casual dresses this fall. I’m so used to sandals in summer. Thanks!! 😊

  14. I haven’t got on the bootcut, flare bandwagon yet. Mainly because of my shorter height and I don’t want to wear heels all the time when I head out for everyday. I’m still trying to figure out jeans to buy. The crop are fine but once Winter hits then what? Lol. I would like to see your post for the straight leg jeans. :)They can be tricky. They can look really dumpy, especially with sneakers if they are too long and tend to just look more like mom jeans. For some reason when I wear straight leg I don’t feel up to date. Could you share the leg opening “range” that is considered straight? They feel like mom jeans to me too at times. 🙂 I guess moms jeans are in style lol but for the younger girls…. Teenagers. :). Funny. Wasn’t it so much easier with all skinnies?…..we bought our shoes and they went with all jeans. :). Your body type must work with all types of rises. That is where I’m having trouble is with the crotch of the rise too long and feels and looks bad, but may like the rest of the Jean. I’ve tried so many. I’m 5’3” 118-120lbs. so shouldn’t be this hard. I’ll keep trying. This is a great, detailed post and can’t imagine the time you spent. The side by side pictures really help see the difference in even just a inch of length either way. Thanks.

    1. Mom jeans are a type of straight leg jeans, so yeah, you do have to be careful or they can look frumpy. It’s more about the shape than the leg opening. If they have any taper at all, they read like mom jeans to me.

      Skinnies were more versatile, for sure, but not sure I’d call them easy. I remember when they were first coming into fashion, and we struggled with how to wear them and women did not want to give up their bootcuts. Then our eyes adjusted and we all figured it out and they stayed around for soooo long, I think b/c of their versatility.

      I feel like we are moving into an era where we will have different leg styles in our closets. I prefer bootcuts and flares with heels so I’ll wear the ankle length styles and straight leg jeans for casual. And we may still pull out our skinnies for wearing under knee high boots.

  15. I just cannot do flares or boot cut that are cropped; it just looks so odd to me. And with mules….ug. I love boot cut and flares otherwise.

  16. I’m looking forward to your post with the straight style! Unless I find a cropped flare or even petite flare that style just won’t work for me… I did find one pair at Banana Republic Factory but definitely needed the petite cropped flare to get it high enough above the ankle! There sure is alot to think about with newer styles and knowing a wider leg makes us look shorter is not what I need at 5’3 😂

  17. Thank you, this was very helpful! I only wish there were more options without the raw hems. I know I can search and find similar with a finished hem, but I really like to link through your posts and buy straight from there. I would love a post like this for straight leg denim too!

  18. Janky?? Is that an official fashion term, lol? Yeah, I don’t like when my booties get caught in my jeans either. I think I’m okay with pairing shoes with flares because I wore them years ago and had no problem figuring out what to wear with them then so it’s all coming back to me now. I never ever wore flats or sneakers with them. I’m short with curves so it made me feel squat. I’m looking forward to a post about pairing shoes with straight jeans. That’s where I get hung up. No pun intended. 🙂

  19. Thanks for doing all this work for us! This must have taken you a long time? Now, I don’t have to try on my jeans & different shoes because you did it for me! The side by sides were very helpful, too. Thanks, again!

  20. I would LOVE to see a post about how to style straight leg jeans as you said in your opening paragraph. Thank you for all the time you devote to these posts!!

  21. Thanks for all the research! Even with this post as a reference I still feel like I’m going to spend a lot of time this fall trying to figure out shoes/jeans combos. It’s a whole new world and I don’t feel quite settled in it yet. LOL

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