How To Wear Oversized Button Down Shirt – Trendy Outfits For Everyone

Expert Opinion By Fashion Writer & Doodler

Ahoy there, fashion explorer! 🚀 Ever found yourself in a thrift store, holding an oversized button-down shirt and thinking, “Is this a tent or a fashion statement waiting to happen?”

Well, if you’ve ever been on the fence about rocking that oversized look, you’re in for a treat. You see, oversized button-down shirts are like the Swiss Army knives of the fashion world – versatile, stylish, and oh-so-comfy.

Now, you might be wondering, “Why should I care about styling an oversized shirt?” Well, because, dear reader, it’s not just a trend; it’s a timeless piece that can elevate your style game to new heights.

I remember once stumbling upon a vintage oversized shirt that belonged to my granddad. It was huge, but with a few tweaks here and there, it became my go-to outfit for casual brunches. And here’s a little nugget of wisdom for you:

Did you know that oversized clothing can actually make you look more proportionate and put-together when styled correctly?

So, if you’re ready to dive deep into the world of oversized fashion, buckle up! We’re about to embark on a sartorial adventure. 🌟

How To Wear Oversized Button Down Shirt In Different Ways?

There are many ways to put on an oversized button-down shirt. Here are some of the most popular ways:


Wear It As A Dress

If you’re looking for an outfit that’s both versatile and stylish, a button-down shirt is a way to go.

A Girl Wearing Oversized Button Down Shirt As Dress

You can wear it as a dress by adding accessories like a belt or heels.

Or, if you want to take things up a notch, try pairing your shirt with some of these other accessories:

A cardigan is another great way to add warmth and texture to your look with minimal effort on your part! It’s also a perfect idea for adding color or texture depending on what kind of look you want.
Scarves are another great way of adding interest without going overboard. We recommend wearing yours at least around one shoulder so that people know where they should focus their attention when looking at you from across the room

Style It With Leggings Or Tights

If you want to take your oversized button-down shirt and make it look more formal, try pairing it with leggings or tights.

A Young Girl Wearing Oversized Button Down Shirt With Leggings

It’s a great way to add some style without breaking the bank!

If you’re feeling more daring, then wear your oversized button-down shirt with a belt and heels.

This will give the illusion that you’re wearing something higher than usual while still keeping things casual enough for everyday use.

If all else fails and you’re still unsure what type of outfit would suit this look best, we recommend trying out sneakers instead!

They’ll allow your shirt to stand out while also keeping things comfortable throughout the day


Pair With Leather Pants Or Skirts

Leather pants or skirts are a great way to add some edge to your outfit.

A Young Stylish Girl Wearing Oversized Button Down Shirt With Leather Pant

They can be worn with an oversized button-down shirt, adding a bit more edge than just wearing a plain T-shirt and jeans.

Leather pants and skirts are versatile and can be worn with many different outfits.

Tuck the shirt into your skirt or pants and add a belt for a more polished look.

Alternatively, you can leave the shirt untucked for a more cool look.


Cinch With A Belt

You can wear your oversized button-downs with or without a belt,

depending on what style of pants you have on and how much room they leave at the waistline.

However, wearing one will help keep everything from falling off when bending over or sitting down.

A Young Stylish Girls Wearing Belt Over An Oversized Button Down Shirt

The great thing about wearing something like this is that it makes any pair of pants look better because they don’t have unnecessary bits hanging out!

It will help you look slimmer and more proportionate, while also adding some volume in the right places.
A belt can be used as an accent piece, adding color or pattern to an outfit. You might want a bright orange belt or one with geometric patterns on it!

Pair It With High-Waisted Jean Shorts

High-waisted jean shorts are in fashion right now, and they look great with any oversize shirt.

A Young Beautiful Woman Holding Laptop Bag, Smartphone, Goggles And Wearing Oversized Button Down Shirt With High Waisted Jean Shorts Outside

You can wear your oversized button-down shirt with high-waisted jean shorts in a variety of ways:

A classic style that is versatile. If you’re looking for something more traditional, this would be the way to go. Your oversized button-down shirt will be eye-catching with high-waisted jean shorts, which are often paired with sandals or sneakers for springtime outings.
Make your outfit stand out with some color! Instead of pairing your classic black straight-leg jeans with a neutral-colored top and shoes from Nike’s Jordan or Ralph Lauren Brand collection, try wearing an olive green or blue denim jacket over top of your favorite pair of jeans.

Layer With A Cami Top

A Young Attractive Girl Wearing An Oversized Button Down Shirt Layered With Cami Top On Street
Choose a cami that is the same color as your button down
Layer with a cardigan or blazer for an extra layer of fabric.
Try a cami with lace detailing or a contrasting color.
Opt for a cami with a bold graphic print

As A Kimono

This is a great way to wear oversized button-down shirts.

A Young Beautiful Girl Wearing Oversized Floral Button Down Shirt As Kimono

The most important thing is that you want your shirt to be long enough so that it covers your knees if you’re wearing leggings or shorts, or just below them if you’re wearing pants.

Then, tie the belt around your waist and pull it tight enough so there’s about an inch at each side of your stomach.

The length should depend on how much room there is in front of your body when tied up;

if there isn’t much room then try tying it at mid-chest instead!

Make sure not too tight though because then all those buttons might pop off!

Kimono is an uncommon look, So if you’re in doubt read this guide to know when you should opt for kimonos.

Tips For Styling An Oversized Button Down Shirt

You can style your oversized button-down shirt with any type of outfit, including:

  • Casual jeans and sneakers or loafers
  • A dressy outfit with a blazer or cardigan
  • A utility jacket and jeans (or khakis)

Below are some tips on how to style an oversized button-down shirt:

If you want to wear the shirt as a dress, make sure the hemline is at least knee-length.
If you’re wearing leggings, make sure the shirt is long enough to cover your bottom.
Wear the shirt unbuttoned and untucked for a more casual look.
Tuck the shirt in for a more polished look.
Add a belt for a more feminine look.
Accessorize with jewelry, scarves, or hats for added style.

How To Find The Right Oversized Button-Down Shirt For Your Body Type!

Not all oversized button-down shirts are created equal!

Here are some tips on how to find the right one for your body type to dress up according to the latest trends:

For Small Bust

If you have a small bust, look for a shirt with ruffles or detailing around the neckline to give the illusion of a larger chest.

For Large Bust

If you have a large bust, look for a shirt with an empire waistline to help minimize your chest size.

For Pear Shaped Body

If you have a pear-shaped body, look for a shirt that is fitted at the waist and flared at the hips to help balance your proportions.

For Hourglass-Shaped Body

If you have an hourglass-shaped body, look for a shirt that is fitted at the waist to accentuate your curves.

For Tall People

If you are tall, look for a shirt with a long hemline so you don’t end up with too much fabric to cover up around your ankles.

For Petite

If you are petite, look for a shirt with shorter sleeves and a cropped length so it doesn’t overwhelm your frame.

Example of a Fashion Designer’s Insight:

Jeanette Madsen, known for her eclectic and bold fashion statements, recently shared a glimpse of her urban style on Instagram, perfectly encapsulating the versatility of oversized shirts.

Her approach to pairing such pieces with city-chic accessories could inspire those looking to add an edge to their oversized button-down shirt ensembles.

Madsen’s ability to blend comfort with style demonstrates the oversized shirt’s potential as a staple in any fashion-forward wardrobe.”


The Bottom Line

Now that you know how to wear an oversized button-down shirt, it’s time to put your new knowledge to use!

Go out and shop one or two and start experimenting with different looks.

With a little practice, you’ll be a pro in no time!

What tips do you have for finding the right one for your body type and styling an oversized button-down?

Share your thoughts and ideas in the comments section below!

How To Style Oversized Shirt!

Tasha Juli
Tasha Juli Korman is a fashion and lifestyle blogger. She has been blogging for over five years now and found her niche in the world of style! Whether it's taking you on a personal journey through her wardrobe or sharing outfits that match your own personal style, you enjoy following along.