Fashion, Finding your style, Outfit Ideas

Bye Bye Skinny Jeans: How To Style Baggy Jeans To Avoid Feeling Frumpy

what to wear with baggy jeans

This article was written by The Zillennial Zine’s fall editorial intern Hannah Yarrington. Find her on Instagram at @513hny. If you would like to share an article with The Zillennial, send us an email at

Among us Zillennials, the era of skinny jeans has come to an end, and we’re moving back to our 90’s roots of mom and baggy jeans. They are objectively more comfortable, and you can choose to style them in many different ways, depending on what kind of vibe you are going for. But many people tend to shy away from baggy jeans for fear of looking “too casual” or feeling like they are being lost in their jeans. So, we’ve put together some ideas for what to wear with baggy jeans and how to style them to avoid feeling frumpy or underdressed.

Tiny on top

One of the best ways to balance out the bagginess of the jeans is to pair it with a more slim-fitting top. This allows you to define your waist more so that you don’t feel like you’re losing any shape and feel more put together. You also create the illusion of an hourglass figure since the baggy jeans will flare out at the bottom rather than coming to a point like skinny jeans tend to do. 

Now, this top does not have to be cropped in order to create this look, and if your shirt is a regular length, try to tuck it into your jeans to give your outfit the same effect. And if you want to dress your baggy jeans up a little, try incorporating a well-fitting blouse to give off that effortlessly cool girl look.

Baggy on baggy

I will start this section by saying YOU DO NOT HAVE TO BE “SKINNY” TO WEAR A BAGGY ON BAGGY LOOK. As a mid-size girl myself, I have been told repeatedly that I should not wear baggy-on-baggy looks because it will make me look bigger than I am and that it is not flattering. And that is simply not the case.

So, when going for this look, my first tip is to find a good quality baggy t-shirt/long sleeve/ sweater that you feel comfortable and confident in. I personally like my baggy tops to hit me right at my hips, and I usually buy them two sizes up. Now, to help you feel a little more put together and structured, I love tucking my shirts in the back into my bra. This helps define my waist more and gives back some of the shape I lacked (but I also love a good baggy silhouette, and I don’t believe we owe it to anyone or have to prove that our bodies have a shape).


It is not necessary to always try to define your figure when going for the baggy look, though it can help when you’re first getting into the style and want to avoid feeling shabby. Another way to elevate your baggy jeans outfit is to layer! Layering a baggy vest, a structured blazer, or a sleek button-up can give your outfit some more interest and make you feel more composed. I love matching this outlier with whatever shoes I wear or just sticking to complementing colors that keep the outfit from looking like there is too much going on.

Pay attention to length and size

When buying your first pair of baggy jeans, there are a few things to keep in mind so that you can have a more flattering look. Let’s first talk about length. I prefer to have my baggy jeans either touching the ground or at least hitting my shoes to keep my ankles from looking awkward and out of place. But if your jeans end up being too long, I like to roll mine once or twice, depending on where I want them to land. 

A common misconception is that if you are wearing baggy jeans, they’re supposed to be baggy everywhere, even your waist. However, you don’t have to have baggy jeans that are falling down your legs. Try looking for a pair that you feel fits you pretty well, or if you are super good at DIYs, you can tailor jeans to fit you better in the waist. That way, you won’t feel like your jeans are giving you a larger tummy area, and it will help you like them a little more.

These are just a few different ideas for what to wear with baggy jeans and how to feel more confident! Let us know what you think in the comments!

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