13 Simple and Trendy Ways to Style an Oversized Button-up Shirt

Angela Boss
by Angela Boss
1 Material
5 Minutes

Hey, guys. If you want to know how to style an oversized shirt, you’re in luck. There are so many options and I’m going to show you all of the ways that I can think of today with a plaid button-up flannel. This top is super trendy right now, so it is perfect to use for showing you different outfits you can choose from. Let’s get started!

Tools and materials:

  • an oversized button up shirt
How to style oversized shirt

1. Crop top and biker shorts

We’re starting off nice, simple, and basic. Anyone can pull off this look and it’s one we can find in all of our closets. It’s just a plain black crop top with some black biker shorts. Your tank top doesn’t need to be cropped; I just like to show a little bit of belly. All I did was put the flannel over my outfit and it looks super stylish, effortless, and comfortable.

All black outfit with sneakers and oversized flannel shirt

I have on a pair of black sneakers to match my all-black outfit.

White tank top and black leggings with a button-up flannel shirt

2. White tank and leggings

Here’s another nice and simple look with the basics we all have in our closets. I just have a white tank top on, some black leggings, and white sneakers with the flannel shirt over them. This is another look that anyone can pull off. It’s so simple but super trendy. You don’t have to wear a crop top, you can wear a white t-shirt, a long tank top, a long-sleeved shirt, or whatever you like.

White tank top and ripped denim shorts with a flannel button-up shirt

3. White tanks and ripped denim shorts

This look is one of my favorites. I just have ripped-up denim shorts, a white tank top, white sneakers, and the flannel pulled over it. It’s a nice, beautiful, go-to summer look.

Ripped denim shorts with a flannel shirt tied in a knot

4. Tied shirt and shorts

Transitioning outfit three into outfit four, just button the shirt right at your chest area. Grab the shirt at the bottom and tie it into a knot. Fix the bottom of your shirt so it looks nice and clean, then take the flaps and tuck them in. Adjust the collar and now you have this cute, cropped shirt with the denim. You can even tie the knot lower to cover your belly, but I like the look when it’s tied higher.

Baggy ripped boyfriend jeans with a tank top and oversized flannel button-up shirt

5. Baggy ripped boyfriend jeans with a tank top

If this look doesn’t scream trend, I don’t know what does. We have some baggy ripped-up boyfriend jeans paired with a crop tank and the flannel over it. I have heels on because I’m short, but you don’t have to wear heels. 

Button-up shirt outfits

6. Baggy ripped boyfriend jeans and off-the-shoulder shirt

To transition outfit five into outfit six, button the top right at your belly button. Then pull it down from your favorite shoulder. Now take the bottom ends and tuck them in on opposite sides of your jeans. Adjust so it lays on your body how you like it, and now we have this cool look. It’s so effortless and sexy at the same time.

Fitted boyfriend jeans with a bralette and loose button-up flannel shirt

7. Fitted boyfriend jeans with a bralette 

I love this look. I just have a lace bralette on; you can wear a lace tank top if that makes you more comfortable. I’m wearing boyfriend jeans that are a little more fitted and are distressed with some sneakers and the flannel shirt over them.

Fitted jeans with dropped shoulders button-up flannel shirt

8. Fitted boyfriend jeans with a dropped shoulders shirt

Let’s transition into outfit eight by buttoning the top at the hip area, and pulling the shirt off your shoulders. I ended up adding another button so it laid nice and securely over my shoulders, but adjust how you need to for your body. Look how cool and cute it is.

Button up outfits

9. Ripped jeans and tucked shirt

Pull the shirt back over your shoulders, and tuck the shirt in on one side all the way until you reach the side of your hip. Tuck the other side loosely into your pocket. This is another effortless, cute look. Tucking into one side really emphasizes the hips and makes the shirt and the body look a lot nicer.

Female styling oversized shirt

Tip: If you’re too hot over the summer, roll up your sleeves and push them above your elbows. Now you’re nice and cool and not sweating.

Oversized button up shirt outfit

10. Dress and loose fitting button-up shirt

Who says you can’t wear a dress or a skirt underneath your flannel? Because you absolutely can! I paired this look with some sparkly sandals.

Tucked flannel button-up shirt over a fitted dress

11. Tucked button-up shirt over a fitted dress

Take the two flaps and tie them low on your body around your hip area. Tuck it in at the back and the front so it looks cleaner, then button it up to your preference. This is really cute and effortless. 

Tight-fitting dress with a high-tied button-up flannel shirt

12. Tight-fitting dress with a high-tied button-up shirt

If you’re a little more sassy and daring, you can tie it higher up. For this version, I tied it up over my belly button. Depending on your comfort and where you want the emphasis to hit, you can tie it lower or higher. I like it like this because it makes me look taller.

Ways to wear a long shirt

13. Bathing suit and button-up shirt 

For lucky outfit number 13, I just have the flannel over a bathing suit. If you don’t have a bathing suit cover - wear a flannel. It looks really good and is so trendy.

How to style an oversized shirt tutorial

That’s thirteen ways to wear a long shirt! This flannel is such a fabulous piece of clothing. It doesn’t matter which age you are, or your preferred style, there’s an oversized button-up outfit for everyone.

Let me know down below which look you liked the most. 

Items used:

Suggested materials:
  • Oversized button up shirt

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