How to Style an Oversized Shirt & Not Look Sloppy
Wearing an oversized shirt can quickly go from effortlessly cool and casual to frumpy and awkward fast. Whether it’s an oversized sweater, button down, or graphic tee, there is a fine line between intentionally styled and just plain sloppy.
So today I am sharing my best hacks for taking an oversized shirt and styling it in a flattering way! I’ll dish on my best style hacks and also share some cute outfit ideas with oversized shirts you can easily copy.
How to Style Oversized Shirts: Easy Hacks
Style Hack #1- If it has buttons, un-button some of them!
Currently, this is a super on-trend to wear cardigans and button downs. Un-button the bottom for a faux peplum effect that defines the waist and also shows off your bottoms more instead of just hiding them under the length of the shirt.
You also un-button a few at the bottom and can tuck just one side and get a cool-girl effect that is both put-together but laid back. The perfect balance.
Lastly, unbuttoning all of them is also always an option too for an extra casual look.
Style Hack #2- Throw a belt on over it.
Sometimes the top is so oversized that a belt is just the thing you need to get some much needed shape and style back into your look. I recommend this for oversized cardigans and sweaters when you want to pair them with looser bottoms and the whole look is just feeling frumpy for some reason.
Style Hack #3- Go for a tuck.
Proceed with caution with this one, but you can definitely go for a full tuck depending on the material of the shirt. Some tops are just too bulky for this to look cute, or your bottoms may be too thin in order for it to work (nobody wants a butt that appears lumpy from you stuffing your top into your pants!
To avoid bunching with a thicker shirt, you can use a fashion tool like the Tucky or there are dupes now on Amazon. I have the OG Tucky, and it totally works!
If you’re a millennial, then you know all about the French tuck! I know Gen Z is allergic to this one, but you can’t lie it looks really chic with the right outfit.
Style Hack #4- Let it go, let it flow.
This one is my favorite because it’s the easiest one. Just wear it straight up untucked, all buttons buttoned, and just let it be!
Now there are some helpful / optional rules to this because when something is super oversized and longer than your butt- I personally find that tighter pants pair well with it. I like to follow the formula of OVERSIZED + TIGHT + CHUNKY SHOE. I think that look is perfectly balanced.
But somethings are just slightly oversized, and actually look good with some wide leg jeans or a maxi skirt. Even a mini skirt!
Here are some examples of when this looks good below:
Oversized Shirt Outfit Ideas to Easily Copy
Graphic Tee & Lace Maxi Skirt
I love this trendy way to rock an oversized tee. This outfit is trendy, comfy but also edgy and on-trend. Rock it with cowboy boots and it works for everything from a concert to brunch.
Graphic Tee, Jeans and Heels
Another fun way to style up a graphic tee is to simply wear it with some jeans and heels. You can tuck it or just wear it as-is and either way will look super chic.
Oversized Sweater and Leather Shorts
In the colder months, on oversized sweater with some leather shorts and tights is a whole look. It’s fun, feels dressy and looks insanely cute all together. It’s anything but frumpy!
Oversized Sweater and Jeans
Simple, but chic! In 2026, we like a wider leg jean with our oversized sweater as the go-to instead of the tried and true legging combo. This look is perfect with some trendy booties, simple jewelry and a fun little shoulder bag.
Oversized Denim Shirt and Satin Skirt
An oversized denim shirt is so fun to style. This way with the maxi skirt is so fun, and you can wear it totally buttoned, partially buttoned, or throw a little graphic tee on underneath and wear it unbuttoned.
White Button Down and Trousers
This look is giving old money. You can easily make this classic white oversized button down feel more styled with layering a sweater over your shoulders.
Oversized Graphic Sweatshirt and Leggings
For a casual school drop off morning, this outfit is a slay. It’s comfy but still looks styled. The puffer vest, slouchy socks and beanie really pull the whole look together and make it so much more than just a sweatshirt and leggings!
Oversized Denim Shirt and Flare Leggings
Adorable, easy and comfy! Another denim shirt look that is so perfect for any casual occasion. Throw is on with a slick back bun and sunglasses and you will look so put together!
Oversized Button Down and Seamless Romper
I love these little athletic / catsuit rompers! They look insanely cute paired with an oversized button down. This is a great look for the spring and summertime when you’re on the go and want to look cute.
Oversized Sweater and Flare Leggings
An oversized sweater is cute on its own, but layered over a turtleneck and with cozy ugg slippers and it’s comfy but not sloppy looking. Big fan of this look and I wear it often!
RELATED: How to Style Flare Leggings (10 Cozy Chic Outfit Ideas)
If you’ve been stumped on how to wear your oversized shirts or you’re scared you’ll look like a frumpy mess, I hope this post gave you a little more confidence in that department. Oversized can actually be chic AF, so experiment with what’s in your closet, and put together some cute looks!
Loved these oversized shirt styling tips and outfit ideas? Be sure to save one of the images below to Pinterest so you can reference them later on!
