How to Style Straight Leg Jeans – Tips for Shoes, Tops, and Silhouettes

How to Style Straight Leg Jeans

Today I’m sharing a few outfits with straight leg jeans and tips for how to wear straight leg jeans. Styling straight leg jeans seems like it should be straightforward, right? (Couldn’t help myself. 😆) But I’ve found that it can be quite tricky sometimes, especially if you’re used to styling a different cut of jeans, like skinny jeans. I often need to be more particular with what I pair them with compared to skinny jeans and bootcut jeans. That’s partially due to my body shape and partially due to the fact that I’ve spent nearly a couple of decades building my wardrobe around skinny and bootcut jeans, so I feel like I have to rebuild parts of my wardrobe (namely tops and shoes) to accommodate. 😩

Of course how much someone has to rebuild their wardrobe will depend on where they’re starting from, what is already in your closet, as well as your body shape. (Like I said, this is not as straightforward as some would think!) Sooooo, I say this all for a few reasons. First, if you’ve felt like it’s not as straightforward to style straight leg jeans, you are not alone! Second, I also kind of want to prepare you that if you want to expand to straight leg jeans, you might need to also expand your tops and shoes to accommodate it, which could get costly. Again, it’ll depend on what’s already in your closet and your body shape. But it could be a lot more work than you originally thought 🙈, so be prepared for that.

I’ll share a few of the things you might need to navigate when styling straight leg jeans along with some outfit ideas. These things certainly won’t solve everything, but hopefully they’ll give you some guidance for how to troubleshoot your outfits and give you some outfit inspiration!


A loooong time ago when I solely wore straight leg jeans, I wore full length ones. Nowadays, I go for an ankle length or crop length for a fresher and more modern look.

Ideally, for an ankle length, I want them to sit right on top of my ankle bone or about an inch above, which will highlight the narrowest part of my ankle. 

Right length straight leg jeans: raw hem straight leg jeans, white top, tan suede flats

This is my personal preference, as I feel this keeps the overall look more modern. I would do longer straight leg pants, as in things that aren’t jeans. For those, I’d be okay with them hitting the top of my foot, below my ankles, as long as they’re not pooling or bunching at the bottom, in order to maintain a straight, clean line. But, at this point, when it comes to jeans, I’m going for ankle length.



This feels like one of the most puzzling pieces for people, especially if we’re working with ankle length straight leg jeans. 

Ankle length straight leg jeans are fairly easy with shoes in warmer months. You can pair them easily with flats, heels, or wedges that expose your ankles and aren’t super bulky at the top of your foot, which helps keep the leg line longer. Shoes like simple ballet or d’Orsay flats, mules, loafers, open toe heels, pumps, open toe wedges, low profile sneakers, etc. all work fairly easily. If they have an elongated toe as opposed to a squat and round toe, that’s even better to help extend your leg line. Even if it’s not a super pointy toe, but just not a very rounded and squat toe box, that’ll help a lot.

Examples below. All the shoes below keep the area around the ankles fairly uncluttered.

Shoes to wear with straight leg jeans: heels, flats, low profile sneakers

When months get colder and you need more substantial footwear like booties or shoes that cover your ankles, this is where my shoe collection doesn’t cut it.

First, what to do. The easiest way to do this is by wearing booties with a shaft that is tall enough so that your jeans cover the shaft of the boot by at least an inch. 

This is also where I personally feel a sticking point with straight leg jeans, and I’m not sure how I will proceed yet. 😆 My colder weather shoe wardrobe is full of boots, booties, and wedge sneaker booties that work perfectly with skinny jeans (and many of them work with bootcut jeans), but it is not set up well for straight leg jeans. And, I’m not sure yet how much I want to spend on a handful of new shoes to accommodate them. Shoes are expensive! Especially boots!

Boots with straight leg jeans: burgundy polka dot blouse, maroon moto jacket, black pants, black boots, gray handbag

Since I don’t currently have proper booties that work with my straight leg jeans, I can’t show you any pictures. Instead, I reached back to a post from a couple of years ago with straight leg work pants and booties that shows what I’m talking about. See how the shaft of the bootie fits under my ankle length straight leg pants? In this case, there is no gap or ankle showing between your shoes and your jeans.

Also, the leg opening of your jeans would need to be wide enough, and the shaft of your booties would need to be narrow enough to allow the jeans to fall fluidly over your booties, not buckling or bunching. (So particular, right?) Otherwise, it’ll look messy as well as it could cut off your leg line instead of help extend it. This is the best option if you don’t want to have bare ankles in colder months.

To see this done with booties and straight leg jeans in a casual way, check out my friend Lauren’s post. I always think of her as the queen of straight leg jeans. They work soooo well with her body type, and she always looks so cute in them. Head over to her post What Shoes to Wear With Straight Leg Jeans. You’ll see her wearing boots in a couple of the examples, both following the same guideline of a shorter ankle length jean with booties that have a higher shaft that is also thin enough to go under the leg of the jeans without getting caught. You’ll also see she’s doing what we talked about earlier with her other examples for wearing shoes that expose the ankles and don’t have a lot of bulk there to keep the leg line long.

As for cold weather sneakers or non-boot options that don’t expose your ankles? Honestly, I have no clue yet! I have a handful of water resistant wedge bootie sneakers that I absolutely LOVED last fall and winter, but they don’t work well with straight leg jeans. So, for practicality’s sake, I might just opt for skinny jeans when it gets really cold and rainy. I loved having simple outfit options for casual outfits that kept me warm AND were water resistant. I loved not having to change or rethink my outfit when it started raining out of nowhere. 

Anyway, those are some shoe options with straight leg jeans for you!


Define Your Waist

Finally, what tops to pair with straight leg jeans. This one is really important and possibly flies under the radar while the boots conundrum gets all the attention. But, the tops you pair with straight leg jeans are equally important. In Simply Put Together, as well as here on the blog, I have talked about the importance of dressing your body shape, not just with individual clothes, but also through how you combine clothing shapes and paying attention to the overall silhouette your outfit creates. If you want a clear example of what I’m talking about, read my blog post Plain to Polished: The Importance of Clothing Shape Combinations.

Wearing straight leg jeans changes the silhouette on your bottom half, which can require you to change what silhouettes you wear on your top half to maintain balance or keep from looking like a shapeless block. This can be very particular and sometimes not particular at all, depending on what your body shape is. But this is why in Simply Put Together we talk through different silhouettes with skinny, straight, or bootcut pants and learning what to wear on top depending on what your body shape is. 

For me, I have natural curves, which is one reason I really love skinny jeans. Straight leg jeans provide a straighter silhouette, so I have to alter what I wear with them and which parts of my body I emphasize or define so that I still have curves and don’t look like a blob.

If you want to learn the ins and outs of how to dress your body shape, (plus learn how to build a wardrobe that perfectly suits you and learn the science behind putting together great outfits and alllll that good stuff), join the Simply Put Together waitlist HERE

And, whether you are interested in SPT or not, here are some things all body shapes can do when styling straight leg jeans:

First, define your waist. Really, this is good practice with any cut of jeans. One way to do this is either by doing a partial tuck with your top to delineate a waistline (gives you better proportions—another thing we cover in Simply Put Together). See the quick example below:

How to Wear a T-shirt with Straight Leg Jeans: black and white striped tee, light wash straight leg jeans, gold pendant necklace, tan flats


Another way to do it without tucking is simply to make sure your top isn’t super long, about one-third way down your body as opposed to, like, halfway down your body, such as this:

How to Wear a Sweatshirt with Straight Leg Jeans: white sweatshirt, light wash straight leg jeans, white earrings, white slip-on sneakers


A third way to accentuate your waist is to tuck in your top tightly all the way around so that it is very fitted, which accentuates your waist the most. I know this makes many women uncomfortable (myself included), so remember, there are two other ways to delineate your waistline above! Personally, I don’t do this regularly with skinny jeans because, since skinny jeans already show off my natural curves, I don’t want even more of my shape accentuated with a tight, formfitting tuck. But, since straight leg jeans don’t hug my curves, I don’t feel *as* self-conscious with a more formfitting tuck. 

How to Tuck in Shirts with Straight Leg Jeans: black and white long sleeve tee, cream cardigan, light wash straight leg jeans, gold pendant necklace, tan suede flats

See the difference? Again, defining your waist is good to do with any cut of jeans, so pick the one that makes you feel the most comfortable and do it! It’ll transform your outfits. 😊


Create Curves

The last bit of advice is to use details in tops to create curves. First off, you don’t have to create curves. This is just something I personally like to do, but I don’t even do it all the time. Some body shapes can really pull off a silhouette with long, straight lines, while for others it can make us look like a block. And block or not, some of you may just prefer a silhouette with less curves, and that’s not bad! It’s only bad when straight lines make you feel shapeless in a bad way. Make sense?

For me, because straight leg jeans offer a straighter silhouette, I tend to feel shapeless in them much more easily than in skinny or bootcut or even boyfriend jeans. (Which I know is weird because boyfriend jeans are somewhat straight too. 🤷🏻‍♀️) Skinny jeans show my natural curves while straight leg jeans don’t. Here are some examples of what I mean:

Skinny Jeans vs. Straight Leg Jeans: white sweatshirt, medium blue skinny jeans, light wash straight leg jeans, white slip-on sneakers, white earrings

The sweatshirt I’m wearing is a straight cut, but skinny jeans show my natural curves at the hip and calves, which offsets the straighter cut top. In the second picture, everything is the same except that I switched the skinny jeans for straight leg jeans. You can see how my shape is a little more rectangular with the straight cut of straight jeans. It’s not necessarily bad and not completely shapeless, but it has noticeably less definition than the outfit with skinny jeans.

Skinny Jeans vs. Straight Leg Jeans: pale pink leopard sweatshirt, medium blue skinny jeans, light wash straight leg jeans, white slip-on sneakers, white earrings

Here is another similar example, this time with a sweatshirt that has volume at the sleeves which can sometimes help create curves or movement. However, the hem of the sweatshirt is still very straight and the neckline is high, plus the sweatshirt has a boxy and voluminous cut. With skinny jeans, it’s easy. They offset the volume and I don’t need quite as much definition up on top because there is enough definition in the bottom half. With straight leg jeans, there is less definition everywhere, so the lines are straighter.

So, if you have been feeling kind of “off” in straight leg jeans, consider whether you need to add more curves or definition elsewhere in your outfits. Again, it will depend on your body shape. Some details that can do that are things like ruffle sleeves, v-necklines, scoop necklines, puff sleeves, balloon sleeves and hi-low hems to name a few.

Some examples below!

Straight Leg Jeans Outfit for Fall: Orange sweatshirt, light wash raw hem skinny jeans, tan suede flats, gold pendant necklace, gray crossbody bag

Balloon sleeves and a curved hem add curves.


Straight Leg Jeans Outfit for Fall: Sage green ruffle sleeve t shirt, light wash raw hem skinny jeans, white slip-on sneakers, white earrings, gray crossbody bag

Ruffle sleeves coupled with a v-neckline add curves.


Straight Leg Jeans Outfit for Fall: White puff sleeve t-shirt, light wash raw hem skinny jeans, tan suede flats, gold pendant necklace

Slightly puffed shoulders offset the straight lines.

Remember, you don’t need to add details like these when wearing straight leg jeans, and also it will really depend on your body shape since some of these particular examples add volume in ways you might not want. But, it’s just one thing I wanted to throw out there as something I do and something for you to consider when troubleshooting outfits. 

Outfits With Straight Leg Jeans

Now, I’ll leave you with a bunch of outfits with straight leg jeans to give you ideas. Some of the pieces aren’t available anymore, but quite a lot are! I included whatever is available or similar options in the widget below for all the outfits!

SIZING: I’m 5’6″ and usually S/M or 6 in clothes and 8.5 to 9 in shoes.



Straight Leg Jeans Options

Here are some options for straight leg jeans. Some are available in straight, petite, plus, and tall.



BTW, if you found the tips about tucking and elongating your leg line helpful, you would really love Simply Put Together! Those are the kinds of foundational style concepts that can be applied to basically all of your outfits so that you can nail put-together looks every time. You’ll learn style concepts, style strategies, how to dress your body shape, the science behind putting together outfits, and more so that you can feel empowered in your own style. Come learn what Simply Put Together is all about by getting on the waitlist for it HERE!

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