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!
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.
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.
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.
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.
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.
These also work well with snow boots on the coldest winter days.
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!)
The Paige Cindy is slightly longer and wider than the styles shown above, and I like them best with boots.
I don’t really care for the Paige Cindy with sneakers and loafers; I prefer to see a little more ankle.
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.
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.
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 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.
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.
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.
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.
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.
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.
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.
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.
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