13 simple and trendy ways to style an oversized button-up shirt (2024)

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!

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Tools and materials:

  • an oversized button up shirt
13 simple and trendy ways to style an oversized button-up shirt (1)

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.

13 simple and trendy ways to style an oversized button-up shirt (2)

All black outfit with sneakers and oversized flannel shirt

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

13 simple and trendy ways to style an oversized button-up shirt (3)

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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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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.

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13 simple and trendy ways to style an oversized button-up shirt (2024)

FAQs

How do you make an oversized shirt look flattering? ›

Leggings offer the ultimate fitted contrast to balance the proportions of a loose top. You won't look frumpy leaving even the most oversized shirts or oversized sweaters untucked or unknotted. Plus, leaving it out helps cover the bum for a more modest look.

How do you wear an oversized trend? ›

Purposefully oversized pieces provide the additional structure you need to avoid looking like all your clothes have stretched on the hanger which just looks scruffy,” says Murray. “You want the items to be oversized in the correct places, like the shoulders and the waist.

How to style an oversized shirt plus size? ›

In order to style the perfect look, it is important to pair the shirt with things that will balance the look. Because the shirt is oversized the bottoms can be leggings or straight leg. Third - try all the options - Cast aside worries of frumpy! The oversized shirt is all about ease and comfort, feel the power!

What to do if button up shirt is too big? ›

Wash In Hot Water. An age-old trick used to shrink oversized clothes, including dress shirts, is to wash them in hot water. Exposure to hot water will cause the fabric to expand, followed by contracting. This thermodynamics will, in turn, shrink your dress shirt.

How do you spruce up an oversized shirt? ›

Here are our seven best hacks for styling oversized t-shirts for your leg days, easy run days, rest days, and everything in between.
  1. Tie In A Knot.
  2. Tuck-It-Under-Your-Sports-Bra Trick.
  3. Go Bold With A Graphic Tee.
  4. Comfy And Cozy With Joggers.
  5. Pair With Leggings Or Shorts For A Casual Gym Outfit.
  6. Up Your Layering Game.

How do you look slim in an oversized shirt? ›

Some ways to make an oversized shirt look good on a thin person are to wear it off the shoulder, wear it with a belt, tuck it into high-waisted pants or skirts, or wear it with a statement necklace.

What body type looks good in oversized shirts? ›

Can oversized t-shirts be flattering for all body types? Absolutely! With the right styling techniques and garment selection, oversized t-shirts can complement any body shape.

Why does Gen Z like baggy clothes? ›

Baggier jeans and looser-fitting pants ultimately emerged as a happy medium between the athleisure worn throughout multiple lockdowns and the constricting skinny jeans of the previous decade. The silhouettes could be sleek and comfortable without compromising one for the other.

Are oversized shirts still trendy? ›

A quick glance at the current fashion trends is sufficient to confirm what fashion insiders have known all along: oversized shirts are the fastest ticket to envy-inducing street style.

What accessories to wear with oversized shirt? ›

Oversized T-shirts pair well with high-waisted bottoms, such as jeans, skirts, or shorts, for a balanced look. They can be dressed up or down with shoes and accessories like sneakers, heels, jewellery, or sunglasses.

How to style a women's button-down shirt? ›

"You'll want an A-line skirt or something that's more fitted at the waist and then flared out slightly. Tuck the shirt into the skirt, roll up the sleeves and throw on some heels for the perfect formal look." Bornstein also likes to use button-down shirts as layers, especially over a tee, tank or bodysuit.

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