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Styling An Oversized Denim Shirt

June 11, 2025Ways to Wear

As a habitual shirt tucker (pretty sure from being a millennial), I’ve started trying to branch out in my style and try the untucked look. Especially with my go-to button down shirts.

I like to have a few short and long sleeve button down options to reach for in the morning. I tend to think more about the bottoms and accessories I’m wearing. Then the shirt is more of a neutral base to build around. So, having a few of these tops ready to go makes getting dressed quick without any fuss. It also guarantees I’ll feel stylish throughout the day.

Banana Republic denim top, J.Crew skirt (similar), Gucci jelly sandals (found a pair on Poshmark or here is a similar option)

I’ve been needing to add a few more options to my arsenal and opted for this oversized denim top. The denim is a lot thicker than my usual button ups so tucking really is not an option. So, I’ve been playing around pairing various bottoms with it.

For me, and I thought I’d be wearing this top with a lot of pants, I prefer it with more feminine and dainty accessories/bottoms. It really feels like such a masculine top that a skirt with a slit or something fitted, sheer, or sparkly make for great contrast and really fun looks! I also love how the clear jelly sandals keep a nice neutral, soft look with the sequins and denim.

I love a gingham skirt as a more casual option. This one is old but I found this beautiful pink one that is super similar (it also comes in other colors). And these woven mules are such a cute everyday shoe option. Especially for work. I’ve had them now for over five years. These flats would also look super chic.

Here are a bunch of skirt options that would look really cute with an oversized denim top!

Agolde denim shorts, Loeffler Randall sheer flats

Lastly, a fitted pair of denim shorts works perfectly. I tried my denim Bermudas but it just felt like too much denim and too drowning on me. Same with my other trouser shorts. These Agolde ones are a favorite and it would also look cute with a pair of white denim shorts.

Here are some great denim shorts (and some other short shorts) to wear this summer both with and without an oversized denim shirt!

Happy styling! Would love to hear which styling option is your favorite!

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