Despite being a millennial who grew up on skinny jeans, I’ve actually grown to love a good not-skinny jean. For years, I was hesitant to give wide-leg or trouser jeans a try because as someone who’s shorter (I’m 5’3″), I was worried they’d be overpowering or make my legs look shorter. But after discovering exactly how to wear not-skinny jeans, I’ve learned it’s all about how you style it.

I recorded a video series that I shared on Instagram in case you want to say that too: Watch part one, part two, part three A, and part three B.

Before we get into my rules of thumb for styling not-skinny jeans, I thought I’d share a few of my favorites. I love having a good variety in my closet — from straight leg to wide leg. Once you scroll down, you’ll see how much each style changes based on the shoes I wear with it. This is why I love fashion! So fun to play around and get creative.

If you’re looking for more inspo on how to wear not-skinny jeans, check out this blog post I wrote a while back! It’s got some helpful tips.

SHOP MY FAVORITE NOT-SKINNY JEANS

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RULE ONE: CREATE CONTRAST BETWEEN WIDTH OF HEM AND TOP OF SHOES

I’ve found not-skinny jeans look best when there’s some contrast the top of my shoe and the opening of the jean leg. This tends to be more of an issue when wearing booties when straight jeans — since there’s not a huge difference in the width of the jean and the shaft of the bootie.

With a wider jean, you’re going to want a skinnier shoe silhouette. Otherwise, it looks stocky (like, it’s giving Spongebob).

In the photo above, you can see the image on the left is way more flattering because there’s a greater contrast. The image on the right sort of looks like a straight line without any contrast.

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rule TWO: when in doubt, show your ankle

This is a great of thumb, especially if you’re wearing sneakers, loafers, or flats.

With sneaker, it’s easy because there’s pretty much always space – even if just sliver – between the top of the shoe and the bottom of the jeans.

For the loafers, we had to measure, but the perfect place for your hem to hit is about 3 inches from your ankle. IMO that creates the perfect illusion of skin showing.

Flats are the easiest since they tend to show the most skin. Unless your jeans are just super long, you’re likely going to show some ankle if you’re wearing flats.

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rule 3: Avoid jeans bunching around the shoe

With wide leg jeans, you run the risk of them, getting baggy at the bottom. This creates a super unflattering look because it shortens the length of the leg (or at least the jean…).

Basically, you want the hem of your jeans to kiss the top of your sneakers or bed of your shoe.

If you look at the example above, the booties on the left allow the jeans to lay flat and elongate the legs. The flats on the right create a bunched appearance that feels… frumpy.