One thing I think we can all agree on is that jeans are just simply a closet staple. They’re comfortable, they’re versatile, and you can create so many looks with them. Right now straight-leg jeans, mom jeans, or whatever you want to call them, are having a major moment.
Gen Z is telling us to ditch the skinny jeans and embrace basically every other style but it seems like. I’m here for it. I really am. And I actually may be here to get rid of 90% of my skinny jeans. But I’m also going to be honest, styling shoes with this style of jeans can be a bit tricky! And even I, as a fashion blogger, am having a bit of a hard time with it.
Before it got cool out, I relied on a sandal or a sneaker to pair with straight-leg jeans. These were easy, no-brainer outfit ideas that always worked. Because truly, so many shoes go with straight-leg jeans!
Now that we’re into fall with the cooler weather, it’s time to pair our jeans with boots. A natural progression of the fashion season, right? And there is 100% a right and wrong way to do this and make it look good. And not to mention, to make sure your ankles aren’t freezing.
How To Style Boots With Straight Leg Jeans
Start With Good Straight Leg Jeans
You want to start your outfit off on the right foot. And that means a good pair of straight leg jeans that you feel great in. I like for these to not be super cropped as it will help pair them with boots if you have a little bit of length to them. This will allow you to wear more of your boots with them.
If you go with a slightly cropped pair, you’ll be showing off your ankles a ton and personally, I’d rather not see my ankles with my straight leg jeans. Leave that for the skinny jeans. And if they’re too long you can always cut the hem on them (my tutorial here) or do a good double cuff to give an edgy look to them.
Slightly Wider Leg Opening
The thing that will make it so much easier to pair a majority of your booties with straight leg jeans, is to choose a pair that has a slightly wider leg opening. This doesn’t need to be a wide leg, or a kick flare, but just not a slim or super tapered straight leg.
While it is still possible to make this work (you’ll see that in some below examples), I personally just find it easier when I choose my truly straight-leg jeans, or the ones that have a slightly wider silhouette to them.
Choose Ankle Boots That Hug Your Ankle
This is the key to mastering this entire look. Straight leg jeans have a slight leg opening to them and in order to pair these jeans with boots, you need to not add any bulk to your ankle. You want the boot to be snug to your body so that the straight-leg jean opening can fall nicely over them. This helps to also elongate your leg and not create a break in the eye.
Plus, having a pair of boots that hits higher on your leg (like mid shaft, doesn’t need to be knee high) will help with accomplishing this. Leave the old school Chelsea boots and low ankle booties in your closet to be worn with your skinny jeans or wide-leg jeans. Instead opt for styles like a sock boot, or mid-calf ankle booties that zip up for a perfectly snug fit.
And if you hate a boot in general, and want to try other styles of shoes, here’s a big post on all the types of shoes you can wear with straight leg jeans. Get even more use of this new closet staple.
Outfit Ideas With Straight Leg Jeans And Boots
Off White Straight Leg Jeans With Boots
If you’re wondering how to wear those white and off-white jeans in the fall and winter, this is it. I’m a firm believer you can wear white denim well after Labor Day. You just have to follow a few rules. And adding a great bootie is the way to go.
Loving both of these looks so much and am officially on the hunt for more white jeans specifically for fall and winter. Because let’s be honest, I’m not wearing anything but shorts in the summer.
Casual And Everyday In Straight Leg Jeans With Boots
Throw on your comfiest low heeled or flat boots with your straight leg jeans and you’re set. A big cozy coat and scarf will keep you warm while out and about. I think this combo is the solution to that ever so annoying issue of having cold ankles when wearing ankle booties with skinny jeans. This keeps you warm and cozy well into winter.
The look on the right is likely a Chelsea boot too. These can work if they’re a bit more snug and tall on the leg. Again, same rule applies here. Many of our old Chelsea boots from the 2000’s and 2010’s are probably going to be cut lower, which may make it a bit hard to achieve this look.
How To Style Straight Leg Jeans With Blazers
A combo I am 100% copying ASAP as you all know I love a blazer. A blazer paired with straight-leg jeans and a cute ankle boot is the perfect combination for date night, a business casual lunch or meeting, or just even to head to a coffee shop to get some work done. Go more casual or more business if you like. This is such a versatile combination.
Mom Jeans With Dr Martens
The one type of boot in my own closet that I currently own that works with a straight leg or mom jeans are my Dr Martens. They work with a straight leg since they have a higher shaft and can be tied to fit pretty snug against your ankles. Making them the perfect shoe to wear with them. This chunky combat boot style is a more edgy take and I’m into it!
PS my favorite Dr Martens boots are reviewed here so you can find the right size and fit!
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MUST READ
Best Straight Leg Jeans
Looking for the perfect straight-leg jeans to complete your wardrobe? Check out my guide to the best straight-leg jeans to shop right now—featuring styles you’ll love and tips to find your perfect fit. Your go-to pair is just a click away
see my picks
White Straight Leg Jeans With A Fall Trench Coat
These white straight leg jeans were a late summer favorite. And for fall, I’m just adding these tan Target sock booties and a sage green trench. It feels like the perfect early fall outfit to transition from season to season. Easing into fall colors and styles.
These are the Madewell Perfect Vintage jeans that are the perfect fit for wearing with sock booties for fall and winter. And they are really the best straight leg jeans to wear as we head into warmer weather as winter starts to fade.
Lug Sole Boots
Straight fit pants from jeans to utility pants, are so perfect for lug sole boots. My number one tip though is to ensure your pants are slightly cropped or else it’ll feel too heavy at the bottom with the lug sole and puddling fabric. You can see in this winter outfit how the pants fall over the top of the lug sole boots and don’t bunch up.
Knee High Boots With Straight Leg Jeans
This is a slightly tricky one as many of us parted ways with our beloved skinny jeans. Pairing a knee high boot with straight leg jeans can be difficult to pull off due to the bunching at the knee that is inevitable. The best tip here is to choose a slim straight leg jean, and a slightly wider knee high boot opening to allow the fabric to go inside the boot. There will be bunching, and that is the look. But if it’s spilling over, the jean is too baggy. And yes, this is why I do say, if you love knee high boots over jeans, you should probably keep one or two pairs of your skinny jeans so that this combination has a cleaner line.
Relaxed Straight Leg Jeans With Heeled Boots
Straight leg jeans don’t have to always hit at or around the ankle. You can have them hit the floor and puddle a bit. This is a more 90’s style or relaxed straight leg jean style.
The type of boot you can wear with these is much more flexible. Since they are a bit more loose around the ankle, you can wear styles that maybe aren’t so snug to the ankle. I prefer a more square or pointed toe boot here. I’d go for a heeled boot so your jeans aren’t totally puddling and looking sloppy.
Depending on how wide your straight leg jeans are, you may even be able to wear your favorite knee high boots under your jeans. The above relaxed straight leg jeans would truly work with almost all of my heeled boots (both ankle and knee high!).
Straight Leg Jeans With Chelsea Boots
One of the most common boot styles to wear for fall and winter is a Chelsea boot. A Chelsea boot can be heeled or flat, just depends. But all Chelsea boots have the elastic side panels allowing you to pull the boot on and off. These flat Chelsea boots are a staple for the cooler months to keep you warm and dry.
To style Chelsea boots with straight-leg jeans, you’ll want to really make sure you’re thinking of the two key factors, slightly wide straight leg jean opening and a taller boot shaft. This will again allow your jeans to fall nicely over the boot.
Newer styles of Chelsea boots are going to have a higher shaft on the leg making it easier to pair with your jeans. This really helps when trying to style them with your favorite new straight leg jeans. Barrel jeans also work great with this too!
And that’s how you can wear all the right boots with your straight leg jeans this fall. You may need to make a few new purchases to round out your closet to make it work, but you’ll be thankful that you have the right shoes to go with your new go-to jeans.
If you want more ideas on what shoes to pair with straight leg jeans, check out this guide! And if you haven’t found the best straight leg jeans yet for your closet, here is my ultimate guide! Lastly, brown boots are clearly one of my favorite things in my closet and I’ve got even more brown boot outfit ideas pairing them with skirts, dresses and more.
