How to Cuff Your Jeans: A Simple Guide to Get You Started

Let me start this off by saying: there is no "wrong" or "right" way to cuff your jeans. This guides is simply that, a guide; to get you started if you're looking for advice on how to cuff your jeans. And the graphics are for easy reference if someone finds this post useful to them. So don't be offended and don't think I'm putting you in a box - I'm just trying to help someone out as if they were in my shoes three years ago!

It is officially getting colder! Maybe not this week in Georgia, but next week is looking promising. But for all of you lucky ones that are enjoying the nice crisp fall weather, you might find yourself dusting off your cute fall booties. And to some people, that may be a daunting task. Because while you have these amazing shoes, you never wear them because you don't know how! You might even find yourself falling in love with a pair of booties in the store and then not getting them only because you have no idea how to style them. Well, this post is here to (hopefully) help you! I'll show you a few ways you can wear those cute shoes with your favorite pair of jeans.

The first time I wore a pair of jeans with ankle boots, I struggled with the right way to cuff my jeans. Now, even after a few years of owning booties, I still struggle with it and have to take time to make sure that they don't look stupid when I do. One thing that was difficult was finding the right kind of jean. Try to get the jeans that are like leggings - "jeggings" - or tight all the way to your ankle. It is easier to roll and cuff them when they are tight and don't leave you with a baggy cuff. Loose jeans will make your leg appear larger around your ankles and calves. But no fear, I have linked many jeggings throughout the post. I have found that the American Eagle jeggings are the best, so there are many of those. In this post, I want to cover several styles of ankle boots - tall ankle boots, ankle boots with a little dip in the front, and some that are a normal ankle height. 

 1. Straight Cut Booties + Ripped Denim

These booties are taller than the average ankle bootie, where the top of it sits just above the ankle. Now these booties are some that you can wear with most any type of jean - skinnies, flared, and boot cut. In these pictures I have only paired them with the skinnies because it is my favorite style. But any of the principles can be applied to any kind of cut. 

First of all, you really don't want to pull your jeans over your shoes. The wider cut jeans, such as flared and a wide boot cut are the exceptions to this, since you want them to come over the boot and almost touch the floor. It covers up your cute shoes!

Next, do not tuck them into the boot. This creates a stumpy look because there is no break in the line of the leg at the ankle. Also, it makes your jeans look way to long for your legs, which is the opposite of what we are trying to accomplish. So, no tucking for this style of boot. I see a lot of bloggers who do this, and I think to myself, "This outfit is so cute, but it would be even cuter if they had just that tiny detail of a cuff."

On this next one, it's kind of tricky. Because my jeans are so long, when I rolled them up once just enough so you could see that piece of skin, the roll was way too high. BUT, if you roll it up to the correct place and it's 2/3 of the length of my roll, then you are good to go. In the very last picture of the post is an example of how long the roll should be.

Ahh, so much better. Here I double rolled mine because my jeans are extra long, so one cuff wasn't enough. But for the most part, you want to cuff it enough so that you can see that tiny bit of skin, which breaks up the leg line and creates an elongated leg - which every girl wants. So keep that roll high enough to see that sliver of skin, but not to high because this boot is already at the top of your ankle, and any higher would most likely make your legs shorter - which no girl wants.

Jeans: American Eagle 1 • 2 • 3 | Booties: Nordstrom 1 • 2 

2. Peep Toe & Chunky Heel + Dark Wash

Again, don't do this - covering up your gorgeous shoes is not something that you should get into the habit of doing - unless the jeans are long and flared. 

 With this bootie, that has a little dip in the front, you don't want too much skin showing on the sides, so cuff your jeans accordingly. As always, we are trying to achieve the elongated leg look while still being stylish. This double cuff shows more skin than just the single and is a great option for a more playful look.

This is a great example of how simply cuffing your jeans once, makes the bootie trend a breeze. The cuff is not too long and it hits right at the top of the boot. This is how I wear my jeans with these booties. (P.S. The chunky heel is a great addition to your closet if you don't already have some)

Jeans: Gap 1 • 2 • 3 • 4 | Heels: LOFT 1 • 2

 3. Neutral Wedge + Light Wash

While these shoes are not my favorite out of the three, these are the best illustration of how to effectively cuff your jeans with ankle boots.

This boot sits right on the ankle, so it looks great with just a normal one roll cuff. Some skin is wanted with just the one roll, but its not paramount that you nee to see it from the side view, as you can see in the below picture. One little cuff is the way I wear them most often because it gives off a casual and easy-going vibe. The lighter section of the cuff provides a great contrast at the hem, breaking up the shoes and jeans and showing those beautiful ankles!

Here is a double roll that shows more skin than most of the other cuffs.This can be either a casual look that can be paired with an oversized sweater or can be dressed up with a great blouse and a boyfriend blazer.

I LOVE this next cuff. It's simple and just looks a little bit more stylish to me. It's and easy and simple one roll, but comes up higher than the others. Even though you may think this would make your legs appear to be shorter, it actually achieves the elongating effect that you want and at the same time looks super chic. 

Jeans: Gap 1 • 2| Wedges: Target 1 • 2 • 3 • 4

As I mentioned before, most people struggle with this concept. But it will only get easier with practice and repetition. And don't be afraid to experiment! If you like a way that I didn't, then rock it. This is just more of a guideline for people who don't know where to start. I didn't cover a lot of way to wear jeans and ankle boots, so let me know how you wear your ankle boots. And happy cuffing!