Fall/Winter
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What Jeans to Wear with Flat Shoes

Today we’re talking about what jeans to wear with flat shoes, inspired by this reader question:

What jeans are we supposed to wear with flat shoes these days? And which flats? I love flares and bootcut, but of course those need a heel. I’m struggling with this issue as I don’t want to wear heels 90% of the time. I’m even struggling with how to wear fashion sneakers with jeans these days. The crops don’t seem right when it’s freezing outside. I honestly don’t love skinnies, but I did not have this problem when they were “in”. Help me, lol!

I wear flat shoes almost every day, for at least part of the day, so I’ve rounded up a few of my go-to outfits so we can discuss the denim and shoe pairings and why they work… at least, why I think they work!

Straight Ankle Jeans with flat Chelsea Boots outfit details

Fun Fact: I actually keep the jeans I wear with flats on one side of my closet, and the jeans I wear with heels on the other. I feel like it makes putting outfits together a lot easier.

Also, if you need help deciphering the various lengths and styles of denim, you may like my post: Women’s Pant Styles and Hem Lengths Demystified.

Best Jeans to Wear with Flat Shoes: Straight Ankle Jeans

Keeping in mind that in matters of fashion, opinions are always subject to change without notice… At the moment, I like straight ankle jeans best with flat shoes, and these are my current favorites.

What Jeans to Wear with Flat Shoes: Straight Ankle Jeans Fidelity Cher // Mother Dazzler // Paige Cindy // AGOLDE Riley // Frame Le High Straight

The AGOLDE Riley Long Jean is a classic straight leg style with a vintage-inspired wash that plays to the current denim trends. I often wear them with my VEJA Esplar sneakers.

What Jeans to Wear with Flat Shoes: AGOLDE Riley Long Jeans + VEJA Esplar AGOLDE Riley Long Jeans + VEJA Esplar

The 28″ inseam is just long enough to keep a long, lean leg line but not interfere with the top of the shoes. In my perfect world, they’d be a half-inch shorter for the sneakers, but they’re perfect with boots and loafers…

Loafers and straight ankle jeans are practically made for each other. They expose just enough skin at the ankle to be slimming and keep an overall cohesive look.

AGOLDE Riley Long Jeans + Sam Edelman Bit Loafers // outfit details

I also like wearing these jeans with lug sole Chelsea boots. They easily slip over top for a long, lean leg line and don’t buckle on top of the boot.

AGOLDE Riley Long JeansLa Canadienne Connor Waterproof Boots // outfit details

The Fidelity Cher is a similar denim style with a slightly shorter (27″) inseam, and they’re my favorite black straight ankle jeans at the moment. I wouldn’t want them any shorter, but they’re just about perfect with most of the flat shoes in my closet.

Of course, if you’re taller or shorter than I am, these jeans won’t look exactly the same on you, but this is the look I like.

Fidelity Cher + similar loafers

These also work well with snow boots on the coldest winter days.

Fidelity Cher + Sorel Explorer Joan

The Mother Dazzler is my favorite pair of white straight ankle jeans. They also pair really well with sneakers and loafers, and they’re also going to be great with ballet flats this season. (Spring Trend Alert: Ballet flats are BACK!)

Mother Dazzler + ballet flats // button-up shirt

The Paige Cindy is slightly longer and wider than the styles shown above, and I like them best with boots.

Paige Cindy + Chelsea Boots // outfit details

I don’t really care for the Paige Cindy with sneakers and loafers; I prefer to see a little more ankle.

Paige Cindy + loafers = not a fan of this

Here’s a side-by-side with the AGOLDE Riley. Even though both jeans reportedly have a 28″ inseam (according to their respective websites) the Paige Cindy is slightly longer and sits awkwardly on the top of the shoe. It’s a subtle difference, but it’s a deal breaker for me.

AGOLDE Riley Long Jeans // Paige Cindy

The solution is to wear jeans that are slightly shorter, like the AGOLDE Riley and Fidelity Cher, or you can go with jeans that are a little bit longer so they break on top of the shoe. Of course, then they are no longer a straight ankle jean.

This is more of a traditional full-length straight leg style… which can also work well with flats. I just don’t have a lot of these in my closet at the moment. If I’m going to wear a full-length straight leg jean, I feel like the relaxed silhouettes look more modern.

Gap Factory Mid Rise Classic Straight Jeans + VEJA Esplar // outfit details

Of course, if you like any of the looks I don’t, feel free to wear them! There is no right or wrong with fashion; I firmly believe you should wear what makes you happy. I’m just sharing what looks good to my eye.

In case you’re looking to add some new denim styles to your closet, I rounded up a bunch of good options for straight ankle jeans at a variety of price points.

Shop Straight Ankle Jeans:

Crop Flares with Flat Shoes

I also like cropped bootcut and flare jeans with flats. Sometimes they’re also called kick crops. The Mother Insider and Citizens Isola are my current favorites.

I wear this style of denim mostly in the spring/summer months with slides and sandals because the shorter length looks more summery to me, but sometimes I wear them in fall/winter with sneakers or mules if it isn’t too cold outside.

What Jeans to Wear with Flat Shoes: Crop FlaresCitizens Isola Crop Bootcut Jeans // Mother Insider Crop Step Fray Bootcut Jeans in Fairest Of Them All & Dancing On Coals

I have the Mother Insider in white (Fairest Of Them All) and the distressed Dancing On Coals wash. Those are probably my two most worn pairs of jeans in the summertime.

These jeans work well with sneakers because the chunky sneaker offsets the wider leg opening, and they show just enough ankle to be slimming. If they were any shorter or longer, they would look awkward. (The Mother Insider has a 26″ inseam and 15″ leg opening.)

I also like the Citizens Isola quite a bit, and I’m happy to see them back this year in several new washes. They have a slightly wider (17″) leg opening. Here’s a outfit I wore when I paired them with mules.

Citizens Isola + Steve Madden mules // ribbed tank

I’m not as crazy about ankle-length flares with flats; at least on me. I feel like they cut off the leg at an awkward spot, so I reserve them for wearing with heels. But if you’re taller, they might be a crop flare on you.

Although, as I look at this picture, I realize this denim + shoe combo actually sort of works. It’s because ballet flats have a low vamp (the part of the shoe that covers the foot) so it shows enough skin to be flattering. Loafers and sneakers have a higher vamp, so they tend to look awkward with ankle-length flares.

Mother Hustler Flare Leg Ankle Jeans + ballet flats // stripe sweater

I didn’t have time to grab a picture of the ankle flares with sneakers or loafers, but I’ll try to do that later and add a picture to show you what I mean.

Meanwhile, I rounded up some crop flares and crop bootcut jeans to shop below. Remember, depending on your height and body type, not all of these jeans will be a crop length on you.

I highly recommend getting to know your ideal inseam measurements for each type of jean so you can compare online. It saves time and the hassle of returning a gazillion pairs of jeans! Most websites provide that information in the product details.

Shop Crop Flares:

Wide Leg Jeans with Flat Shoes

Wide leg jeans and relaxed straight leg styles are finally hitting the mainstream this season, after being fringe trends for the past couple of years. My eye is slowwwwwly adjusting to this look. I’m seeing a lot of sneakers and lug sole loafers with these denim styles.

I just got these Mid Rise ’90s Loose Jeans from Gap Factory. I don’t love this wash, but I’ve been playing around with them to see how I might style this silhouette.

They work well with sneakers like the VEJA Esplar, and they definitely look best with shorter tops, like this stripe cardigan.

Gap Factory Mid Rise ’90s Loose JeanVEJA Esplar // stripe cardigan

These High Waisted Wide Leg Jeans are from Old Navy. This is where denim styles are going, and these jeans are actually very comfortable. I’m kind of digging them! I like them best with sneakers, but I’m also seeing them styled with flat sandals, which will help transition them to spring.

Old Navy Wow High Waisted Wide Leg Jeans + P448 sneakers // striped sweater (S)

And here’s a pair from KUT from the Kloth. I like this silhouette, and how they fit a little closer through the hips and thighs than the ones above. The welt pockets are cute too.

 KUT from the Kloth Meg + VEJA Esplar // navy stripe sweater // ivory stripe sweater

I need to play around with these some more; I’d like to try them with the ballet flats. Meanwhile, I rounded up some more relaxed straight and wide leg jeans for you:

Shop Relaxed Straight & Wide Leg Jeans:

Can You Wear Bootcut Jeans With Flats?

When discussing what jeans to wear with flat shoes, we’re often told to steer clear of full-length bootcut jeans, but I actually don’t hate this look. A pointy toe flat might look better, though.

Style Tip: I front-tucked the top to keep the overall outfit proportions in check.

  Citizens Lilah Bootcut + ballet flats // floral blouse

These jeans are flares, but they almost read as a relaxed straight. The chunky lug sole loafers help balance the wider silhouette, and I actually like this look. It’s just a tad too masculine for my personal taste, but this denim + shoe combo works if it’s your vibe.

Madewell Perfect Vintage Flare + Bradley Lugsole Loafer // old sweater

Skinny Jeans with Flats

Of course, skinny jeans are always an option with flat shoes. While they aren’t exactly trending at the moment, they can be styled so they look relevant. I don’t think they’re going away. In fact, rumor has it they’re already starting to make a comeback… although I’m sure they will be tweaked to look fresh and new in some way.

If you’re going to wear skinny jeans with flats, I recommend an ankle length or crop style. They look best when they show some ankle. Or you can always tuck them into snow boots or tall boots.

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photos: Alison Cornell

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32 thoughts on “What Jeans to Wear with Flat Shoes

  1. Thank you, Jo-Lynne! I really need this type of guide right now! Styles seem to be changing so much and so fast right now. It’s fun but also easy to feel like I’m getting a bit of whiplash! There are so many trends and so many silhouettes out there; It feels a bit like anything goes! Which is fun! But also requires a great deal of confidence in one’s own personal style eye! Thanks for offering some grounding thoughts on how to grow that eye! Blessings! Krista

  2. Of course skinnies are sticking around and “coming back” cause there has been a revolt among the majority that realize that most of us look frumpy in straight, boot cut, flares…lol. I tried I really did, and now have 4 pairs of jeans that I put on and immediately take off and go back to my skinnies. I’m sure I’m not the only one.
    I honestly feel it was a fashion industry ploy to sell new styles thus increasing profits and sales.

  3. Thank you for your fun fact – I am definitely going to separate my jeans by heel versus flats, too! I am SO happy to see ballet flats making a comeback!

    Any recommendations for premium denim for more pear shapes? The struggle is real with the back gap and/or tight in thighs.

    1. I have the same problem. I buy curvy fit jeans (usually a size smaller than non curvy jeans) from White House Black Market or occasionally from Talbots. I don’t buy regular fit jeans anymore because of the waist gap and having to wear a belt all the time (and even then they feel like they slip down). Try some curvy fit!

  4. Great post – so helpful! Sadly, I can no longer wear heels over a couple of inches and this gives me great guidance. Thank you!!

  5. Thanks Jo-Lynne! I was wondering about flat shoes with wider cuts, like bootcuts and flares. I just bought a pair of wide-leg jeans and want to play around with them. I have loafers and pointed-toe flat boots so I’m sure I will find some combo I like! I’m having fun with the different styles.

    But…am I the only one who doesn’t like ballet flats?? I especially don’t like the rounded toe, plus my feet don’t stay straight in them–does that make any sense?!

    1. I also don’t care for ballet flats. They offer no support for my high arches. I always feel even shorter in them since I’m 5’4. I had a pair with a wedge heel that was about 1 inch that I really liked. Unfortunately I’m incredible hard on all my shoes so those only lasted me a couple of years before I had scuffed them to the point they needed to be tossed.

      1. Robyn I agree. I don’t like ballet flats or skinny jeans. Ballet flats slip out of my feet. I like the way square toe ones look. The round toe look juvenile to me. I’m over skinny jeans. I don’t mind slim straight especially ankle ones.

    2. Funny! I didn’t know so many ladies don’t like ballet flats. I have always liked them, they’re more feminine than loafers and more comfortable than pointed toe flats. 🙂

      1. I’m not a fan of ballet flats because with a very high arch and narrow heel, I just walk right out of them. I think fit is 90% of why I wear the shoe styles that I wear. As far as the wider straight jeans (I like slim straight), I’m finding that anything that harkens back to the early 90’s, when I was in my 20’s, are usually a hard no for me. I think they look great on current 20 somethings, but make me feel like I’m trying to dress as a 20 year old again. Let’s all pray that super low rise do NOT come back.

    3. Me! I loathe ballet flats. I’m not sure I’ve ever even owned a pair because I can’t even keep them on my feet when I’m walking around in the shoe store. LOL I did recently buy a really cute pair of flats that have a ballet flat look to them with a mary jane strap that buckles. They are the Sugar Mary Jane Flat from the brand Trotters. I’ve never worn their shoes before but so far I’m pleased. They have decent arch support and they are made from the softest leather.

  6. Thank you for this post! How do you like your veja sneakers? I’ve been deciding whether or not to get them. Some people say they are uncomfortable. Wondering what your experience has been with them? Thanks!

  7. What about when wearing socks? Most of these looks are without socks and they look great. However there are those of us in colder climates where socks are an absolute must for months of the year.

  8. When I turned 60 I decided that I would focus on what works for my body before worrying about fashion trends. I have a pair of Talbots barley boot cut jeans that I had shortened to wear with a very low heel (nearly a flat) and I think they look fine. I agree that the straight leg and wider leg styles can look frumpy but I think some of that has to do with the light washes that are popular now. Dark and medium washes may not be trending but they’re more polished and slimming. I still own light wash jeans because I like the way they pair with neutrals and I prefer them in the summer, but I stick to the slimmer leg styles in light wash and buy dark wash for my boot cuts.

    1. Some say that bootcut jeans are actually the most flattering jeans and I agree. I have a pair in dark wash for fall and winter and one in light wash for spring and summer. I also enjoy straight leg, wide leg and “lantern” leg, all in medium wash There are so many styles out there that I think it is all about what you feel the most attractive in. I’m just happy there are many alternatives to skinny, which I wore for years, but am ready to put to rest.

      1. Yes, bootcut jeans are supposedly universally flattering. Skinny jeans actually are not, according to most body type experts and stylists. They’re easy and versatile, but not really the best look for most women. (Although, I loved them! LOL)

  9. I love this post. Would you consider doing a graphic for spring/summer like you did in the fall with this information?

  10. My office is on the more casual side of business casual, and the bottom half of my current favorite “uniform” look is dark rinse demi boot jeans with pointed toe flats. Comfortable for walking around the parking lot and office but still polished.

  11. Thanks Jo-Lynne – this post is very helpful for me and thanks for the tip of separating the jeans! I hardly ever wear heels, so this post is really on target for me. I look forward to ordering a couple of the jeans you showed – your guide for jeans fit is also very helpful! I appreciate the informative, relevant posts that you share with us, I always enjoy reading them (and learning)

  12. I just don’t like the relaxed wide leg style. Adds visual weight and too old school for me. Does anyone remember the Star jeans? Lol My sweet spot for ankle crop is 26 so usually have to buy 27 and cut off. Before I cut I try several shoe options to make them work with the most heel heights. I prefer ankle crop with sandals and mules so I’m still struggling with Winter shoe/boot pairings. I need hemmed jeans now. Most mine are cut off. I don’t mind straight leg jeans if they aren’t full length. Full length in me for some reason looks dated and looks awkward with shoes. Can’t wait until Spring to start being able to show more skin with denim and shoe pairings as much easier. I think for me I just have to put the jeans on and once on, my eye tells me if they are right with a certain shoe. I just cut off a pair that wasn’t working and now they went from dated to modern. 🙂 They are the LOFT girlfriend jean.

  13. What about clogs? (Like classic dansko clogs/nurses clogs) At this point in my life, they are my only comfortable option other than athletic shoes (nit cute fashion sneakers) because of plantar fasciitis. What would they go best with?

    1. I don’t consider them flats, so I didn’t include them, but I love clogs. I think they look good with most denim styles, actually. Also, athletic sneakers are actually trending, so yay! 🙂

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