How To Style Oversized Shirt | Stylists Recommendations For 2024

Expert Opinion By Fashion Writer & Doodler

Over the last decade, oversized shirts have become more popular than ever.

But how to style oversized shirts and what exactly are they?

Oversized shirts have been around for decades—they were all the rage in the ’90s and 2000s—but now they’re making a comeback.

What makes this trend so interesting is how these shirts are worn:

They’re being paired with an assortment of garments that are designed to flatter their wearer’s body type (think: long-sleeved tops and dresses that show off your shoulders).

So if you’ve been considering adding an oversized shirt to your wardrobe but aren’t sure where to start, we’ve got you covered!

We’ll cover everything from styling tips for wearing them in general (and which ones work best) to specific trends like boyfriend cuts and our favorite ways to wear oversized tees for maximum impact.

How To Style Oversized Shirts For Every Occasion?

If you’re still on the fence about whether or not to add oversized shirts to your wardrobe, we’ve got plenty of inspiration for that too.

First, let’s look at how to wear oversized shirts.

As with any other piece of clothing, it’s important that you know how to style them correctly so they look good and fit well.

Here are some styling tips:


Oversized Shirts Outfit Ideas For Daytime

A Woman Wearing White Oversized Shirt With Black Leather Pant And Black Sneakers While Holding A Black Leather Handbag
Daytime Oversized Shirt Outfit

If you’re looking for Daytime Oversized Shirts Outfits, there are several ways you can do it.

You can wear your shirt with jeans and sneakers or even with heels.

Or if you want something more casual, then pair it with some low-slung pants and some cool accessories like a statement necklace or bracelet.

The key is finding the right fit in terms of size and style that works best for both yourself and the occasion at hand!

  • If you want to show off your figure, pair an oversized shirt with bodycon shorts or a mini skirt. Tuck in half of the shirt and leave the other half hanging out.
  • Oversized denim shirts are the perfect way to add some edge to a girly look. Try pairing it with a floral dress and sneakers for a cool and casual vibe.
  • For something a little more put together, try tucking a white oversized shirt into high-waisted black pants. Add some heels and statement earrings to really make your look pop.

You can try the above-mentioned outfit ideas but there are 3 iconic ways to style an oversized shirt.

A Stylish Women Wearing Oversized Shirt With Jeans, Heels And Hat
A Stylish Women Wearing Oversized Dress Shirt With Sandals And Holding A Handbag
A Beautiful Girl Wearing Oversized Shirt With Leggings And Sneakers
Oversized Shirt + Leggings + Sneakers
Oversized Shirt + Skinny Jeans + Heels
Oversized Shirt Dress + Sandals or Flats

Oversized Shirt Outfits For Night Out

Two Pretty Girls Wearing Oversized Shirts For A Night Out

Oversized shirts also look great when dressed up for a night out.

  • Look for a shirt that is knee-length or longer. This will help you make sure it doesn’t hang too low in front, so you don’t risk looking frumpy.
  • Pair with a skirt or dress that skims your mid-thigh area. If you have long legs, look for skirts with an elasticized hem at the bottom so they can be pulled up over your knees easily and avoid any unflattering panty lines.
  • Use a belt to cinch in the waist area—this will help create balance on top of all that extra fabric! You could also use an angled belt if desired.
  • Throw on an oversized graphic tee with some ripped jeans and strappy sandals or heels. Add a jacket for an edgy touch.
  • Try tucking your shirt into a shimmery mini skirt and add some sky-high heels. Finish off the look with some sparkling jewelry and you’re good to go!
  • For a more laid-back night out, pair an oversized plaid shirt with some joggers or ripped jeans. Add a bomber or denim jacket and sneakers for a cool and trendy outfit.

Below are classic styling ideas for Nighttime Oversized Shirts Outfits:

A Young Attractive Woman Wearing Oversized Shirt With Clutch
A Young Woman Wearing Oversized Shirt With Shorts And Pumps
A Young Lady Wearing Oversized Shirt With Leather Jacket, Jeans And Heels
Oversized T Shirt + Leather Jacket + Jeans + Heels
Oversized Shirt + Blazer + Jeans or Shorts + Pumps
Oversized Shirt Dress + Statement Necklace + Clutch

Casual Oversized Shirts Outfit Ideas

A Beautiful Woman Wearing Oversized Shirt Tucked In Denim Shorts, Hat And Sneakers While Holding A Camera
A Beautiful Girl Wearing Oversized Dress Shirt With Straw Hat And Black Sandals
A Young Girls Wearing Oversized Graphic Tee With Trouser And Joggers
Oversized Shirt Tucked Into Denim Shorts + Sneakers
Oversized Shirt Worn As A Dress + Straw Hat + Sandals
Graphic Tee or Oversized Sweatshirt + Joggers + slides

Oversized Shirts – A Flashback

A Checked Oversized Shirt

Oversized shirts are simply shirts that are larger than your usual size.

They can be either loose-fitting or baggy.

Oversized shirts are great for both men and women and can be worn in a variety of ways.

In fashion and style, nothing truly comes new under the sun. Oversized shirts have enjoyed a recent resurgence in popularity, but they’ve actually been around for decades.

The trend first came into full swing with the late ’90s grunge movement and became a staple of hip-hop culture and was worn by rappers like Jay Z and bands like Nirvana, Pearl Jam and Alice in Chains were wearing them on stage and off.
They have since become a part of fashion history as well, being worn by designers like Yohji Yamamoto and Alexander McQueen.
Oversized shirts were popular again during the 2000s when they showed up on everyone from Justin Timberlake to Britney Spears to Christina Aguilera (who wore one at Super Bowl XXXVIII).
And now you can find them everywhere: at your local Target store or Urban Outfitters; even on Vogue editor Anna Wintour!

The oversized shirt is also a timeless piece of clothing that can be worn at any time regardless of what trends are currently popular.

So you don’t need to worry about trying to re-invent this classic style!

Important Considerations To Wear Oversized Shirts

Important Considerations For Oversized Shirts - Featured Image

You should know that there are some things you should do if you want an elegant look when wearing your oversized shirt:

Choose an appropriate color palette – It’s important not only how much contrast there is between colors but also how many tones there are within each hue (for example grey vs white). You don’t want your entire outfit looking too matchy by pairing all black pieces together, nor do want an overwhelming amount of contrast as seen on models who wear mostly black clothing with bright accessories such as red lipstick or blue eyeshadow.
Pair them with pants (or skirts) in color combinations that complement each other; this will help your outfit feel balanced overall.

If you love wearing oversized shirts but are not sure how to style them to look both on-trend and flattering, keep reading.

Benefits Of Wearing Oversized Shirts

Benefits Of Wearing Oversized Shirts - Featured Image
Oversized shirts are great for layering because they can be worn over other clothing items to add layers and create more volume. For example, if you’re wearing a long-sleeved button-up shirt with pants that fit closely around your waistline, wear a plus-size shirt overtop of it so that it has enough coverage on top of the dressier jacket or coat.
You can also use oversized shirts as an alternative to adding jackets when temperatures start dropping—just throw on an oversized tee underneath! This will help keep warmth in while still giving off a casual vibe at work or school without sacrificing style points.
Oversized tees also make great covers up when paired with shorts/pants instead of skirts/dresses; they will keep warm legs covered while preventing any panty lines from showing through!

Frequently Asked Questions

How do you wear an oversized shirt stylishly?

There are many ways how you can style your plus-size shirt. You can wear it with leggings, jeans, shorts, or a skirt. It all depends on the occasion and how you want to dress up or down. If you want to dress down, you can wear your oversized shirt with a pair of leggings and sneakers. This is a great outfit for running errands or going to the gym. If you want to dress up your outfit, you can wear jeans and heels. This is a great outfit for a night out or a date. You can also wear it as a dress. If it’s long enough, you don’t even need to wear anything else with it. Just throw on a pair of sandals or flats and you’re good to go. This is a great option for a beach day or a relaxed summer day.

How do you style an oversized baggy shirt?

1. Tuck It Into A Pair Of High-Waisted Jeans
2. Layer It Over A Slip Dress
3. Let It Hang Loose Over Joggers
4. Transform It Into A Cardigan
5. Make A Statement In All White
6. Style It With A Midi Skirt
7. Cinch Your Waist With A Belt
8. Oversized Shirt + Leather Jacket + Skinny Jeans + Heels

Are oversized shirts still in style?

Yes, oversized shirts are still in style. They are a great option for both men and women and can be worn in a variety of ways. You can dress them up or down, depending on the occasion. So don’t be afraid to experiment and have fun with it!

What to do if a shirt is too oversized?

If a shirt is too oversized, you can always try to tuck it in or knot it at the waist. This will help to create a more fitted look. You can also try rolling up the sleeves or wearing a belt. These are all great ways how you can make a big-size shirt work for you.

How do you style oversize shirts and leggings?

There are many ways how you can style your oversized shirt with leggings. You can wear it with a pair of sneakers for a casual look. Or you can dress it up by adding a leather jacket and heels. It all depends on how you want to style it and the occasion.

What are some of the best brands for oversized shirts?

There are many great brands that offer best oversized shirts. Some of our favorites include ASOS, H&M, Forever 21, and Zara. These brands offer a variety of styles and colors that will suit any taste. So be sure to check them out!

Can you wear an oversized t-shirt as a dress?

Yes, you can definitely wear oversized t-shirts as a dress. Just make sure to pair it with the right accessories and shoes. If you want to dress it up, you can add a pair of heels or sandals. If you want to dress it down, you can add a pair of sneakers or flats. It all depends on your personal style and the occasion.

Priyanshi Otwani
Priyanshi Otwani is a Fashion Writer and Doodler based in Mumbai, India.She has been working in the fashion industry for over ten years and has worked with various magazines like Grazia, Elle, Cosmopolitan among others. She also collaborates with brands on designing their products. Priyanshi loves to doodle when she gets time which she shares on her Instagram.