12 Casual Outfits with Boyfriend Jeans

by Ashton - January 21, 2021

It's not really a secret that I love boyfriend jeans. The past year, I've actually worn them more than my skinny jeans. I think they're more flattering on my curves and more forgiving. They're also easier to move around in than most of my skinnies and are a better fit for where I'm currently at in my life.

This is my favorite pair that I currently own. They're currently on sale but only available in a few sizes. My other favorite pair is several years old, but pretty similar to my current fave. This is the closest to both those styles. I also have a less torn up pair made by Kut from the Kloth that I got in a StitchFix box several years ago. The exact style is no longer available, but this is pretty similar.

If you like your jeans to be more clean-cut, check out these two options below.

Now for the fun part. How to style them. Like I said earlier, I tend to wear mine more casually, due to the fact that my favorite pair to wear is toeing the line between distressed and destructed.

With their looser silhouette, boyfriend jeans can look sloppy when paired with the wrong tops and shoes. So how do I keep my outfits looking intentional and not frumpy?

Make sure they fit properly. They're supposed to be loose, but not so loose you're swimming in them.
Balance the looseness of the jeans' fit with a more structured top.
Fake a structured top by knotting it at the bottom or front tucking it.
When in doubt, tuck your shirt in completely and wear a belt.
If you add a third layer (jacket, cardigan, etc), keep it waist-length.
Your jeans should always rest above your shoes. Roll them if you have to. Do not tuck them into boots.
Shoes shouldn't come up past your ankles.

Now, here are 12 ways I've worn my boyfriend jeans over the last year. I hope they inspire you to add a pair or two of these type jeans to your closet!