How to Style an Oversized Shirt

“But I come back stronger than a 90’s trend”, Taylor Swift in Willow. While she meant it to show her own strength but 90’s trends have really made it back and they aren’t going away. While some of them I can do without, low rise jeans for example, but some of the others have been fun to try again. Oversized shirts are a trend I’m really loving. My favorite trends are ones that integrate into your wardrobe easily and refresh it. In this post, I am sharing tips and outfit ideas on how to style an oversized shirt.

How to Style an Oversized Shirt

Play with Proportions

Proportions are important for any outfit but really provide the balance needed when wearing something oversized. When creating an outfit find an item to style with the oversized shirt that is fitted. The contrast not only provides interest but helps to be more flattering. Oversized items paired together can overwhelm your body and add bulk where you may not want it. But when you add a slim bottom with the oversized shirt, it creates balance! Another way to contrast the oversized shirt is to wear it open with a form-fitting top. This will show your shape.

Add in Contrasting Pieces

The oversized shirt I’ve been wearing the most is a collared button-down. I think it has the most versatility. Even when it is in oversized form, it still has preppy vibes. By styling it with items that are in a different style, like athleisure or even sequins, an outfit has a lot more interest. If you are wearing more of a t-shirt-style shirt, think about leather or preppy pieces to add. Whatever style of oversized shirt, find a way to add something a little unexpected with it!

Style as a Jacket

Just because it is a shirt, doesn’t mean you have to style as one! In the Spring especially when temperatures vary throughout the day, light layers are a must! An oversized button-down can be the perfect light top layer. Style it like you would a jean jacket over tops, dresses and even with shorts.

Add Polish

Oversized items need some polish to pull the outfit together. Polished pieces are another way to create balance and interest in an outfit. Polish can come from an accessory or another piece of clothing you put with it. Beautiful gold jewelry adds polish, like necklaces, bracelets or even a watch. Shoes are a great way to add polish. A sleek pair of boots or flats can look polished and so can a pointy toe heel. A really structured, dark pair of denim can even have polish.

Oversized Shirt Outfit Ideas

Oversized Shirt and Biker Shorts

Quick, easy and a little bit 80’s! This is the best spring weekend outfit for running errands or a casual brunch. It’s comfortable while still having a lot of styles. I wear a version of this at least a couple of times a month in the Spring. You can change it up by wearing the button-down open over a t-shirt.

If you don’t have any biker shorts yet, these Spanx ones are the only ones you need. They have just the right amount of compression to be flattering yet still comfortable!

Oversized Shirt and Crop Top

Crop tops are back as a big trend but one that can seem a bit intimidating to wear. Some crop tops show off a lot of skin and others just a sliver. If you want to try out the trend but not show a lot of skin, an oversized shirt is perfect! Layer it over to cover you up a bit but still shows off the crop top.

Finish off the outfit with jeans and polished accessories. A simple heeled sandal elevates the outfit and elongates your leg. I have a post here on comfortable ones!

Style as a Coverup

I struggle to find cute cover ups that aren’t super expensive. I’ve learned an oversized shirt like a button-down is one of the best ones I’ve found. It also can take you from the pool or beach to lunch so easily. They make you look put together but are super comfortable and easy to pack and wear.

On it’s own an oversized button-down is all you need. A white one will work with any swimsuit or you can have fun with a pretty color or print. If you want more coverage to add your favorite jean shorts!

Oversized Shirt with Tailored Shorts

For the Summer it is key to know how to style an oversized shirt with shorts. I like the mix of styles in an outfit when you pair tailored shorts with an oversized t-shirt. It keeps the outfit a little more casual but still polished. Tucking the shirt into shorts keeps the fun volume at the top but won’t overwhelm your frame.

The tailored shorts and shirt are the perfect blank slate for some great accessories! You can really go crazy if you want and add a statement piece or two. I love to treat headbands as a piece of jewelry and to wear fun printed ones. They aren’t just good for covering up a bad hair day.

More Oversized Shirts

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How to Style an Oversized Shirt