Oversize Shirts Are Trending—Here's How the Fashion Set Wears Them Perfectly

For the past few seasons, it's been all about oversize clothing. As a modest dresser, I've always gravitated toward looser tops, so I've been taking thorough notes on how the fashion set has been styling them. While I still love the fitted look on certain occasions, you'll most likely find me in oversize shirting for the foreseeable future. And whether it's a baggy sweater or roomy poplin shirt, I've been saving outfit ideas for them all. You've probably seen all the trending "big shirt, little pants" videos on TikTok and Instagram, but these outfit ideas stretch far beyond just that.

It's easy to wear a big shirt with leggings, but the ideas I've shared below will have you playing around with new pieces and getting more out of your wardrobe this season. Below, I've rounded up the most standout looks in case you wanted some more inspiration. Keep scrolling for more, complete with shopping options to inspire you further.


Bright Oversize Poplin Shirt + Wide-Leg Jeans
(Image credit: @greceghanem)

A colorful and oversize poplin shirt isn't as intimidating as you think. All you have to do is slightly tuck it into a pair of relaxed jeans, and you're good to go.


Oversize T-Shirt + Blazer + Relaxed Jeans
(Image credit: @mimixn)

T-shirts can be made chic too. Just tuck them into jeans or trousers and add a blazer on top. It's the outfit idea that will always work.


Oversize Button-Down + Midi Skirt
(Image credit: @abimarvel)

Instead of trousers, try pairing your button-down with a skirt. You can tie the bottom of the shirt into a knot and then tuck the ends in to change things up.


Oversize Sweater + Puddle Pants + Classic Belt
(Image credit: @lindatol_)

There's nothing like a baggy and comfy sweater. Tuck any knit of your choice into loose trousers and finish the look off with a classic belt.


Oversize Poplin Shirt + Relaxed Trousers + Sporty Sneakers
(Image credit: @jordanrisa)

As I said, a loose poplin shirt tucked into relaxed bottoms will always work. This time, switch out jeans with black slacks and add sporty sneakers. 


Oversize T-Shirt + Maxi Skirt + Sneakers
(Image credit: @emilisindlev)

Since maxi skirts usually have a looser fit, you might feel too intimidated to wear a bigger proportion on top. But tucked in with a belt, the look works. I also think sneakers complete the look effortlessly. (I can thank Bella Hadid for reminding me of that combo.)


Oversize Button-Down + Pleated Miniskirt
(Image credit: @lucywilliams02)

And when you don't want to wear a maxi, opt for a mini. A "big shirt and little skirt" combo is one the fashion set will not be retiring anytime soon.


Oversize T-Shirt + Loose Denim + Knit Scarf
(Image credit: @annelauremais)

Don't be afraid to layer accessories with oversize silhouettes. Instead of wearing a thick blanket scarf, this thin knit scarf is the ideal pairing for a big sweatshirt or T-shirt.

Next, Blanket Coats: The Outerwear Trend Going Viral on TikTok

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.