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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
And this one too. This is my early fall date night outfit formula right here.
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.
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.
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 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.
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.
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.
And I know we’re talking about shorter lengths, but platform sandals also look great with full length flares.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Stay In Touch
If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.
I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.
This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!