How to Style Oversized Shirts for Women

If you’re a devotee of slimline and bodycon silhouettes, you might be unsure about trying out the oversized shirt trend. With a bad fit or styling, oversized shirts can look boxy or even frumpy.

But when styled correctly, they look breezy, chic and effortless. Don’t worry – we’ve taken all the guesswork out of the equation for you! Scroll on to learn how to style oversized shirts and look your very best.

Are oversized shirts in style?

Yes! From formal button-ups to relaxed T-shirts, the oversized fit is very much in style this season. The key to making an oversized silhouette look modern is to shop for structured pieces that are deliberately oversized – not just your regular shirt in a larger size.

How to wear oversized shirts

Here are a few basic oversized shirt outfit ideas to help you get started. Try wearing your oversized shirt:

As a dress

This is one of the easiest ways to up your fashion A-game. Slip into an oversized shirt worn on its own as a dress, pairing it with a blazer and boots or T-shirt and sneakers. You can cinch in your shirt with a belt too if you like.

With a blazer

Cover up with a blazer to give your oversized shirt some extra structure and polish. For an oversized shirt formal look, team a black blazer with a white shirt, tucking in the top.

Off the shoulder

For a casual oversized shirt outfit, go off the shoulder. Choose a plain white T-shirt with a looser silhouette, letting one side hang off the shoulder to show off your collarbone area. You can wear this with pants or high-waisted shorts.

How to style oversized shirts with jeans

Many of the most stylish casual oversized shirt outfits involve pairing a top with jeans. Here’s how to wear oversized shirts with two different silhouettes.

Baggy jeans

You’ll look ultra-relaxed with a loose silhouette from top to toe. Try wearing an oversized shirt with slightly baggy straight-leg jeans and ballet flats, adding a pair of sunglasses for running errands like a starlet.

Skinny jeans

Styling an oversized top comes down to proportions, and skinny jeans are a great fit. Their form-fitting silhouette pairs neatly with a more relaxed fit up top. This is a great chance to try wearing your oversized shirt off the shoulder, with the front of your shirt tucked into the skinny jeans to show off your waistline. Keep accessories minimal for a modern look.



How to style oversized shirts with skirts

Styling your oversized shirt with a skirt can be a bit trickier. If you choose a flowing skirt, the look can be too messy and undone.

On the other hand, an oversized T-shirt looks spot-on with a denim skirt. Both pieces are comfortable, and you can use the relaxed-on-top and tight-on-bottom proportion we’ve described above. Look for a figure-hugging button-through denim style, accessorizing with sneakers or platform shoes.

How to style oversized shirts with shorts

For warmer weather, denim shorts and an oversized white shirt are a classic combo. Just add sneakers and a tote bag for running around town or heading to brunch in style. Bike shorts are another silhouette that works well with oversized tops and T-shirts, giving a flattering silhouette that leans into the athleisure trend. Finish the look with a blazer and crossbody bag.

And now you know how to style them! Whether you prefer a classic white boyfriend shirt or colorful designs, browse our selection of oversized smart shirts to stock up on wardrobe staples.