How to Wear Oversized Shirts? 5 Flattering Looks and Styling Tips

If you’re like most women, you probably have a few oversized shirts in your closet but don’t know how to wear them in a flattering way. Is that right? We’ve put together 5 looks and tips on how to wear oversized shirts of different types!
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how to wear oversized shirts

General Tips for How to Wear Oversized Shirts

First, a couple general tips before we get into how to style different types of oversized shirts.

  • If the shirt is too long and baggy, try knotting it at the waist or side. This will give your outfit some shape and make it more flattering.
  • If an oversized shirt is feeling a little too relaxed, try pairing it with some tight-fitting bottoms like skinny jeans or leggings. Alternatively, you could also tuck it into a pair of high-waisted trousers or shorts.
  • And lastly, don’t be afraid to experiment with different proportions. An oversized shirt doesn’t have to completely drown your frame – sometimes wearing an oversized top with more fitted bottoms can look really chic.

Remember the reason why oversized clothing became popular – it was comfortable and easy to wear. Keep that in mind when styling your outfit and make sure you feel good in what you’re wearing! It’s no use looking fabulous if you’re not comfortable. If you’re unsure how to wear oversized shirts, trust your intuition.

How to Style Oversized Button-Down Shirts?

Button-down shirts are a wardrobe staple and can be worn so many different ways. When you’ve got an oversized button-down, there are a few key ways to style it so it looks chic and not sloppy.

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One way is to leave a couple of the top buttons undone and pair the shirt with a tank top and some high-waisted trousers or denim shorts. This look is perfect for a summer day spent exploring the city or running errands.

Another way to style an oversized button-down shirt is by layering it over a fitted turtleneck or long-sleeved top. This is a great way to stay warm in the colder months while still looking fashionable. Simply tuck the button-down into a pair of high-waisted jeans or trousers and you’re good to go!

If you want to wear your oversized button-down as a dress, that’s also an option! Just make sure to wear a slip underneath or leggings if you don’t want it to be too revealing. And, as always, a pair of heels will dress up any look!

How to Style Oversized T-Shirts?

T-shirts are probably the most popular type of oversized shirt. They’re comfortable, easy to wear, and can be styled in a variety of ways. One way to style an oversized T-shirt is by knotting it at the waist and pairing it with some high-waisted shorts or a skirt. This is a great look for a summer day spent lounging by the pool or running errands.

Another way to style an oversized T-shirt is by tucking it into a pair of high-waisted jeans or trousers. This look can be dressed up or down depending on how you accessorize it. For a more casual look, pair your T-shirt with some sneakers and a denim jacket. For a dressier look, add some heels and statement earrings.

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How to wear oversized shirts as dresses? Make sure to wear a slip underneath or leggings if you don’t want it to be too revealing. You can accessorize this look however you’d like. Add a belt to cinch in the waist, or layer on some jewelry to dress it up.

5 Complete Outfits With Oversized Shirts

Ready to try on some oversized shirts? Here are some complete looks to get you started! We won’t mention any colors so you can work with what you have in your closet. But as a general rule of thumb, you want your shirt to be the star of the show. So keep your bottoms and accessories neutral and let your shirt shine!

  1. Oversized button-down shirt, high-waisted shorts and sneakers: This look is perfect for a day spent exploring the city. It’s comfortable and easy to wear, but still looks put-together.
  2. Oversized T-shirt, high-waisted jeans and heels: This is a great look for a night out. The T-shirt is comfortable and the jeans are flattering. The heels dress up the look and make it more stylish.
  3. Oversized button-down shirt, high-waisted trousers and a blazer: This is a great office-appropriate look. The button-down shirt is professional, but the oversized fit keeps it from looking too stiff. The high-waisted trousers are flattering and the blazer pulls the whole look together.
  4. Oversized T-shirt, denim skirt and sandals: This is a great summertime look. The T-shirt is comfortable and the denim skirt is flattering. The sandals keep the look casual and relaxed.
  5. Oversized button-down shirt, fitted turtleneck and high-waisted jeans: This is a great look for the colder months. The button-down shirt provides an extra layer of warmth, while the fitted turtleneck keeps you from looking too bulky.
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Do you already have an idea for how to wear oversized shirts? We hope one of these looks inspired you! And, as always, don’t be afraid to experiment with different styles and looks until you find what works best for you.

Pull Your Oversized Shirts Out of the Closet and Start Experimenting

Oversized shirts are a great way to add some style to your wardrobe. They can be dressed up or down, depending on how you style them. And now you know how to wear oversized shirts without looking like a slob. Use these styling tips to start experimenting with your own looks. You might be surprised at how great you look!

Have any other questions about how to wear oversized shirts? Leave a comment below, and we’ll be happy to help!

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