Fall/Winter
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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, with leg openings 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 2023, 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. In fact, a lot of websites use the terms interchangeably, I’ve noticed.

Vince silk blouse (S) // PAIGE Laurel Canyon Flares (29) ($50 off at Saks) // Marc Fisher 3 1/4″ booties (8)

Flares & Bootcuts: Shoe Pairings for Fall 2023

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) // similar Sam Edelman Western Boot (8) // Evereve ribbed tank (sold out)

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?

Here’s how the AG Farrah bootcut jeans look with a lower heel square toe bootie. These boots (similar style here) have a streamlined silhouette with a square toe and a 2 1/2″ heel. They look okay with these jeans, but in my perfect world, the jeans would be a little shorter.

AG Farrah 32″ Fray Hem Bootcut Jeans (28) // similar bootie (8) // Nordstrom Signature cardigan (sold out)

These MOTHER Raw Hem Flare Jeans have a 31″ inseam with a 20″ leg opening, so they’re an inch shorter than the AG Farrah, and I like this length a lot better with these boots. It’s amazing what a difference an inch can make.

MOTHER 31″ Weekender Fray Flare Leg Jeans (29) // similar Vince bootie (8) // Halogen sweater (sold out)

Next, I tried the MOTHER Raw Hem Flares with a rounded toe bootie. I don’t mind this look, but I like these jeans better 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 usually wear them with light wash jeans.

MOTHER 31″ Weekender Fray Flare Leg Jeans (29) // similar Aquatalia boots // Nordstrom Signature sweater (sold out)

In this case, I don’t mind the rounded toe bootie with flares (ON SALE!) because the boots have a platform, giving them some extra height, and the lighter wash jeans read more casual. Plus, the henley top is lends a more casual vibe, as well, so the entire outfit looks cohesive.

Paul Green lug sole booties (8) (similar) // MOTHER Weekender flares (29) // henley top (S) // similar belt

But when in doubt, you simply can’t go wrong with dressy pointed toe boots and flares. The Marc Fisher Ulani Pointed Toe Bootie has a 3 1/4″ heel, which is perfect with the 32″ inseam on these jeans for a more elevated look.

PAIGE Laurel Canyon Flares (29) ($50 off at Saks) // Marc Fisher booties (8) // Vince silk blouse (S) // Treasure & Bond leather bomber (S)

Okay, moving on. I think we can all agree that bootcut jeans 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 Sudbury Clogs have a 3 3/4″ heel with a 1″ platform, so the heel drop is just 2 3/4″, and they pair beautifully with these corduroy flares with a 32″ inseam.

Gap Factory 32″ Flare Corduroy Pants (29) // Kork-Ease Sudbury Clogs (8) // cotton sweater (S) // topcoat (S) // Coach bag

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. I know this is “a look” right now, but I can’t help but feel like it only works on the under-40 crowd.

The rest of us probably wore this look in the early aughts, and it just should not be repeated after a certain age. It looks sloppy to me, not intentionally cool, which is the idea if you’re going to wear it now.

MOTHER 31″ Weekender Fray Flare Leg Jeans (29) // rag & bone Retro Sneakers (39) // similar top (S)

Full Length Flares + Heels: Vavavoom!

When you want to level up, full length flares look really good with pumps and dressy heels. These Vince Camuto open toe slingbacks (more color/size options) have a 3 3/4″ heel, which may sound high, but they’re actually quite walkable. I love this look.

PAIGE Laurel Canyon Flares (29) ($50 off at Saks) // Vince Camuto Frasper Sandal (8) (more color/size options) // Vince 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) // similar sandals // 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 pumps with the 3″ block heel are one of my favorites.

Marc Fisher Varla Pumps (8) // PAIGE Laurel Canyon Flares (29) ($50 off at Saks) // Vince blouse (S) // Treasure & Bond biker jacket (M)

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, as shown on the model, or even the ballet flat/Mary Jane combo that’s trending right now, if that’s your vibe.

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 clogs.

PAIGE Claudine 28″ Ankle Flare in Slater (29) // Kork-Ease Darby Clogs (8) // sweater vest (sold out)

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.)

PAIGE Claudine 28″ Ankle Flare in Slater (29) // Kork-Ease Darby Clogs (8) // MOTHER 31″ Weekender Fray Flare Leg Jeans (29) // Kork-Ease Darby Clogs (8)

Clogs also work with crop flares and crop bootcut jeans. These are the Citizens of Humanity Isola Cropped Bootcut Jeans, and they have a 26 1/2″ 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 of Humanity Isola Cropped Bootcut Jeans (29) // Kork-Ease Darby Clogs (8)

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 a few years old, but it shows you how this pairing works together.

UGG Judi Clog (9) // MOTHER Insider 26″ Crop Step Fray Bootcut Jeans (29) // 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.

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 (29) // Seychelles sandals (8) // similar jacket

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 26 1/2″ inseam with a 16 1/2″ leg opening. That extra inch makes all the difference.

Citizens Isola 26 1/2″ Cropped Boot (29) // Seychelles sandals (8) // sweater vest (sold out)

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) // floral top (sold out)

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 26 1/2″ Cropped Boot (29) // MOTHER 31″ Weekender Fray Flare Leg Jeans (29) // PAIGE Claudine 28″ Ankle Flare in Slater (28)

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

  Citizens Isola 26 1/2″ Cropped Boot (29) // similar Marc Fisher booties (8)

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) // similar Marc Fisher booties (8)

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 these have a bit of a heel.

pumps // sandals // boots // clogs

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 (29) // similar Steve Madden mules (8) // Seychelles sandals (8)

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 26 1/2″ Cropped Boot (29) // similar Steve Madden mules (8)

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 26 1/2″ Cropped Boot (29) // similar Steve Madden mules (8) // Evereve ribbed tank (sold out)

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 31″, 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 (29) // Veja Esplar (29) // sweater vest (sold out)

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.

Citizens Isola 26 1/2″ Cropped Boot (29) // Veja Esplar (39) // sweater vest (sold out)

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.

PAIGE Claudine 28″ Ankle Flare in Slater (29) // Citizens Isola 26 1/2″ Cropped Boot (29)

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 (29) // Citizens Isola 26 1/2″ 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.

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

  1. “For now, I plan to keep my full length flares for heels and wear crop and ankle length styles with everything else.”
    Great summary! This is what I’ve been doing.
    You’re great at explaining why things do or don’t work. I can look at a combo in the mirror and say “yes” or “no” based on my intuition, but it would be difficult for me to verbalize the way you do.
    I agree with several others that a post like this about straight leg jeans would be super helpful.

  2. Oh my gosh, what a fantastic post! So thorough!! Thanks for your analysis & insights! So helpful! As an aside, so glad skinny jeans are moving aside for a wider silhouette. As a broad shoulder woman, I never felt that the slimmer pant styles were that flattering or comfortable for me. I’m enjoying the refreshed looked while it lasts!

  3. I find it pretty easy to pair shoes with flares and bootcuts. I feel like almost any heeled shoe works. A decade or two ago when flares/bootcuts were big, I would even wear knee high boots under my jeans, mostly for warmth but also because I don’t recall booties being so popular back then. Can you do a post on dressy and casual booties and knee-high boots? I’m looking to update my boot wardrobe and that’s what I wear during the cold season. Not clogs, flats or loafers. I’m especially looking for boots that are around 2 inches are less but still “cute” – which is totally subjective, lol.

  4. Fabulous post. Really helped me narrow down what new jeans to buy. I am 5’2” so I think I will skip flares and focus on bootcut. That was my intuition but this post really helped to confirm.
    Thank you

  5. Great post, love the side by side pictures and details of what works and what doesn’t. I also would like a post on what works with straight leg jeans. Thanks for all you do!

  6. Great post! Thank you Jolynne for all your hard work! I love your style! I am retired and simply don’t need so many options however, I do like to stay on trend and want to feel good in what I wear and choose. Also being retired, spending over $200 for a pair of jeans and a blouse simply does not make sense. Could you possibly do a post on jeans for less than $100? I understand the jeans you style are high quality and complement many figures.

    Thank you for considering. Kelley

    1. Kelly….. I like Wit n’ Wisdom jeans. Good fit and good price. I have several and they hold their shape. Jo- Lynne has also shared them before.

  7. Thank you Jo-Lynne! I love how you go through this like it’s a “science experiment” of some sort, lol,…it’s so helpful!!

    Do you have some sort of chart in your closet reminding you of the inseam/rise/leg openings on all of your jeans – or do you just remember which ones look best with which type of shoes/tops, etc? I feel like I can never remember the differences in each of my jeans until I try them on again!

    1. LOL, no I’m nowhere near that organized. I just remember. Or I try a few pairs until I get the look I like. But once I wear a pair of jeans and shoes together, I usually remember that I like that pairing and tend to repeat it often.

      1. I wonder if it would be helpful to use a black Sharpie marker and add the inseam on the care instruction tag somewhere in the jean. Especially if you know exactly how a 28″ 29″ or 31″ jean would fall on your leg?? I do try to hang my shorter denim, and longer, flared ones together in my closet.

        1. Sue, I have plastic ties that I attach to my jeans hangers. Using a Sharpie, I have a short description of the jeans and more importantly, the length. I have dividers for the different lengths and this really helps me find the correct length of jeans that I want to wear.

  8. I have been hemming my flares and bootcut jeans (keeping original hem) where they are slightly shorter in front than the back. I like them where they don’t create a bend on the leg in the front but still look longer in the back. With flares, if you have to cut them too much they lose some of the flare width and look more like a bootcut width.

  9. Yep! Great post! I found a great deal on the Kork Ease clogs on Nordstrom Rack and pulled the trigger. So glad I did. Thanks for continuing to show how versatile they are!

  10. Very helpful post! I love a bootcut but flares are just too much fabric for me. It’s great that they are both in style again. Can I ask you a question about a mule/clog. What do you think about the Sorel Hi-Line mule? I kind of like them because they are a little different for a clog but I’m not sure and I obviously can’t make a fashion decision on my own! Thanks!

    1. Elizabeth. I love the Hi Line heel mules. I say get them. :). I have a very similar shoe but mine are alittle more narrow looking. I just wore them yesterday. Same color. If you do get them order through link Jo- Lynne shower then she gets the credit. 🙂

  11. This post is so helpful for my 5’1″ height, thank you.

    Also, your new blog design is very eye catching and classy!

  12. I have been following you for several years and must admit, several items in my closet came directly from your “influence”, so thank you for all you do. In my opinion, this is one of your best posts to date.
    The comparison pictures are incredibly helpful and for some reason seeing the outfit on you helps me more than me looking in the mirror even though we have almost identical measurements.

  13. Great post. So informative. I pretty much follow your advice with the shoes. Being 5’2 I really like bootleg and flare when they are high waisted. They make my short legs actually look long especially with heels. I don’t like a length that bunches at the foot. That’s supposed to make your legs look shorter according to the petite bloggers I follow. Thanks for taking the time to explain everything to us.

  14. Wonderful post, thank you so very much for all your hard work. I’d love to see shoe pairings and even more tops with straight leg jeans. For those of us with picky feet sometimes boots and heels don’t work well. I’d love to see some timeless and classic outfits with said items.

  15. Outstanding post! Thank you so much for doing all of these comparisons and try-ons. This is very helpful and I want to bookmark it for reference.

  16. Maybe this might help shorter ladies like myself (5’2.5″) and just over 70. I have the Kut from the Kloth Kelsey in royal blue crop inset flare which have a 16″ leg opening and 11″rise. Ordered from Zappos on sale and Northstrom also had them. I laundered them before wearing and hung out to dry since they are a darker wash and they did not shrink and have just enough stretch to feel good. Love them and they are not too off the top looking for my age. Have been looking for flares for awhile now and most are just too long and extreme for me; I really wanted the Citizens Isola Jolynn is featuring today but price point just too much for me since retiring.
    Jolynn, I love those Seychelle sandals still eyeing them! Such a great informative post, thank you!

    1. By the way, the Kelsey has the frayed hem and after washing I was able to cut off the long strays and they look much better, had even thought about hemming them but I’m leaving them just as they are.

  17. I just wanted to thank you for this post!!! Just this morning, I asked myself what shoes do I own that will look best with my new Mother Weekended Fray Flares! This was such a huge help!!! Thanks so much for all you do, searching out these wonderful clothes and trying them all on! Much appreciated!

  18. Thank you for another great post! Very helpful! I have gotten much better at trying on different outfit combinations since I started following you. Prior I would put on a pair of pants and shoes and if I didnt like how it looked, I just assumed that it was because one of the pieces just wasn’t right for me. It sounds simple enough, but I never really thought to mix and match my closet it really makes such a difference !

  19. Thank you for this post! I have been struggling with pairing shoes with the different lengths-this really helped!!!

  20. I thought this post was very helpful. I’m not able to wear high heels so I appreciate suggestions wearing lower heels and flats. Thanks so much!

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