Bold And Beautiful: Tips For Styling Your Oversized Shirt Like A Pro

Key Takeaways
  • Pair your oversized shirt with fitted bottoms like skinny jeans or leggings to create a well-balanced and flattering silhouette.
  • Consider adding a belt to cinch the waist and create definition, transforming the oversized shirt into a chic and tailored look.
  • Tucking in the front of the oversized shirt or tying a knot at the waist can add a touch of casual charm and prevent the look from overwhelming your frame.
  • Elevate your oversized shirt outfit with statement accessories, such as bold earrings or a stylish handbag, to bring a polished finish to your overall look.

“According to  Fashion Stylist Expert, styling an oversized shirt is about achieving a deliberate balance. Pair it with slim bottoms and elevate the look with statement accessories for a chic and effortlessly stylish ensemble.” 

Style an oversized shirt effortlessly by embracing proportions, cinching at the waist for definition, and experimenting with layering and textures.

Play with accessories, tuck or roll for a polished look, and mix patterns and colors for versatility. Tailor when needed, but above all, exude confidence in your fashion choices.

In fashion, styling an oversized shirt offers a canvas of creative possibilities. Yet, the challenge lies in achieving a harmonious balance that exudes comfort and chic elegance.

The problem often surfaces when the shirt’s relaxed fit becomes overwhelming or appears shapeless.

The action involves strategic pairing and accessorizing, allowing the wearer to transform an oversized shirt into a deliberate fashion statement.

This article guides you through the solution, offering insights and tips on how to style an oversized shirt effortlessly, unlocking a world of versatile and comfortable fashion that doesn’t compromise style.

Finding an outfit that is both comfortable and stylish can be a big ask these days.

If you choose comfort, you are left with an outfit that definitely wouldn’t make it onto the front page of a fashion magazine.

However, if you choose the stylish option, you can barely sit down or walk down the street due to discomfort and impracticality. 

How To Style An Oversized Shirt

The question that we are forever asking ourselves is how do we incorporate both style and comfort?

We have been living in a world of super-skinny jeans and tiny tank tops that have prevented many of us from bending down to tie our shoes.

If you want a more sophisticated, stylish, comfortable look, then the next part may seem too good to be true. 

Oversized shirts are the perfect combination of style and comfort that suits any occasion perfectly.

Purchasing an oversized shirt ensures that your outfit is casual and a relaxed fit as well as adding an element of sophistication and professionalism.

An oversized shirt isn’t just made for the workplace, it is a key item in any fashionista’s wardrobe. 

Unsure of how to style an oversized shirt? Well, we have some tips for you. By using these style tips, you will be able to style an outfit that is both relaxing to wear and in keeping with current trends.

Wearing an oversized shirt will help you to feel more confident in your look and be comfortable a the same time. After all, comfort is confidence!

Before you get started

  • Understand your body shape to tailor oversized shirt styling choices that flatter your figure.
  • Achieve a harmonious look by balancing the volume of the oversized shirt with more fitted bottoms or structured accessories.
  • Explore different silhouettes, such as tucking in parts of the oversized shirt or tying a knot at the waist, to add variety to your look.
  • Experiment with layering, whether it’s adding a tank top underneath or a stylish jacket over the oversized shirt, to create depth and interest.
  • Mix and match textures and patterns to add visual intrigue to your outfit, creating a dynamic and stylish ensemble.

Here are the best ways to style an oversized shirt if you are unsure how to incorporate this item into your wardrobe. 

1. Tucked In

Tucked In

This may seem like a boring way to style an oversized shirt, but it is in fact, the opposite.

Tucking your standard-sized shirt into your pants is usually considered a traditional workplace look, but with an oversized shirt, you are adding a designer flair to an already smart look. 

If your oversized shirt is made out of materials like poplin cotton, when tucked in, the shirt adds more volume to your outfit and adds a retro element to your look.

Alternatively, tucking a silk or lightweight fabric shirt into your pants or skirt will elegantly drape to provide both comfort and sophistication. 

You can pair these shirts with either pants or different length skirts as tucked in, the shirts will complement lots of different items of clothing.

You can wear mini skirts, maxi skirts, tailored pants, or jeans for an effortlessly stylish look. 

Elevate Your Look: Quick Guide to Styling an Oversized Shirt

  • Chic Versatility: Style an oversized shirt by knotting it at the waist for a flattering silhouette, or layer it with a belt for added definition and style.
  • Smart Pairing: Balance the loose fit with fitted bottoms like skinny jeans or leggings, and consider tucking in the front for a polished yet relaxed vibe.
  • Accessorize Strategically: Elevate the look with accessories like statement belts, chunky jewelry, or a sleek pair of boots to add personality and flair.
  • Maintenance:  Opt for gentle washing and air-drying to preserve the fabric and shape.

2. Classic Striped Shirt

Classic Striped Shirt

Image By @laurenrosebell via Instagram

A striped shirt is a classic staple to any wardrobe as it is stylish, lightweight, easy to wear, and the possibilities of how to wear the shirt are endless.

With an oversized striped shirt outfit, it is easier than you think to get shape in your outfit without looking swallowed up by the oversized shirt. 

Leaving the top 4 or 5 buttons of the shirt open leaves your chest exposed for a relaxed fit whilst still showing some skin and adding a stylish flair.

Alternatively, you can leave the last few buttons unbuttoned to expose your stomach which adds a modern and sophisticated twist to the crop top whilst giving you shape and style.

There is also the option to wear the shirt completely unbuttoned with either a stylish bralette or crop top underneath. 

The striped shirt can be paired with lots of different outfits from different colored jeans, cigarette trousers, skirts, and shorts to add a relaxed and casual element to your outfit.

The shirts can also be worn as light jackets over maxi dresses or jumpsuits. 

3. Retro Tied-Up

Retro Tied-Up

If you are looking to add a vintage feature to your look, then look no further than wearing your shirt all tied-up.

This look has been popular throughout the 50s and 60s paired with a midi skirt for a sexier take on a tucked-in shirt, and in the 70s, the tied-up shirt style was very popular due to its relaxed look and providing you with more shape and edge. 

It is important to find an oversized shirt that is oversized enough to be tied into a bow and it can be tied as tight or as loose as you want.

The top of the shirt can be as relaxed or as casual as you would like as you can either button up the remaining buttons or leave them undone with a stylish bralette underneath. 

Your tied-up shirt can be paired with a number of outfits such as baggy shorts, jeans, mini skirts, or maxi skirts as they add shape to your outfit whilst also providing comfort and style.

Wearing your oversized shirt tied up will keep you cool and comfortable during the heat. 

4. Edgy, Grunge Look

Edgy, Grunge Look

Keep in mind

  • Understand your body shape to choose styling options that complement and flatter your figure.
  • Maintain balance by pairing the oversized shirt with more fitted bottoms or structured pieces to avoid an overly baggy look.
  • Play with different silhouettes by trying various tucking and knotting techniques to add interest and variation.
  • Experiment with layering to add depth to your outfit, whether it’s with a tank top underneath or a stylish jacket over the oversized shirt.
  • Create visual interest by mixing textures and patterns, balancing bold and subtle elements for a dynamic overall look.
  • Elevate your oversized shirt ensemble with thoughtful accessories, such as statement jewelry, belts, or eye-catching shoes.

The grunge look consists of a lot of oversized clothing so if you want to embrace the oversized look, then definitely give this look a try!

Flannel is a staple pattern for grunge outfits so finding an oversized flannel shirt will perfectly complement this look and help you to feel edgy and stylish at the same time. 

The oversized flannel shirt can be left unbuttoned and worn over the top of an oversized t-shirt, so if this is the look you want, make sure to get a larger shirt so it comfortably fits on top of your t-shirt.

You can also wear the shirt over a crop top or bralette, or you can do up a few of the buttons. 

You can pair the look with ripped jeans, skinny jeans, mini skirts, or oversized jeans, it is up to you!

You can make this look as oversized or as tight as you want, and using an oversized flannel shirt will perfectly style your edgy grunge outfit. 

5. Oversized Tee

Oversized Tee

A simple yet stylish outfit can be put together as easily as pairing an oversized tee with skinny or baggy jeans.

This look is effortlessly stylish and you can even accentuate your outfit by sporting a french tuck, where you tuck the front of your shirt into your pants to accentuate your figure. 

The great thing about this outfit is that it can be made up of any t-shirt and any pants. An oversized plain white tee and blue mom jeans is a classic outfit, but you can also try different colors or prints to make your look more interesting.

You don’t even have to tuck or french tuck your tee if you want a very relaxed and casual look. 

You can wear these outfits with sandals or boots and with a cross-body purse for a super stylish look. Accessorize the outfit with gold or silver jewelry and an oversized sun hat for a relaxed yet fashionable statement. 

Pro Tip

For a chic and polished look, experiment with rolling or cuffing the sleeves of your oversized shirt. This simple adjustment adds a touch of sophistication and keeps the overall appearance well-balanced.

6. Classic Button-Down Oversized Shirt

Classic Button-Down Oversized Shirt

A classic white button-down shirt isn’t the most interesting item of clothing that has ever been owned, but there is a way of perfectly styling an oversized white button-down shirt in a stylish way.

First, find a white shirt that fits the same length as a mini dress and you have found the perfect oversized white shirt to style. 

Pairing the oversized white shirt with nothing else and wearing it as a dress is definitely a statement and puts a very fashionable spin on traditional office wear.

This look can be worn casually or for an occasion with the right accessories and can also be paired with a belt to give the shirt some definition. 

You can wear this look with sandals or trainers with a sun hat for a relaxed daytime look, and then with heeled boots, a belt, and gold or silver jewelry for a sophisticated yet stylish nighttime look. 

7. Oversized Patterned And Colored Shirts

Oversized Patterned And Colored Shirts

Patterned Oversized shirts are a great way of incorporating more color and fun into your wardrobe as this can be done effortlessly.

Patterned shirts can be as colorful or as monochrome, as you want and surprisingly, you can pair a patterned shirt with lots of different pants as you can experiment with color or even pattern clashing. 

Monochrome oversized shirts are perfectly paired with white pants for a relaxed and tasteful look, and linen pants provide effortless chic.

You can french tuck the shirt into your pants or allow the shirt to hang over the pants.

With colored patterned shirts, you can incorporate a color explosion of different colored pants that match with colors of the shirt to keep your look fresh. 

You can style these shirts with belts or other accessories as you can make them look as sophisticated or as casual as you would like. Pair with chunky gold earrings for a very on-trend look. 

8. Oversized Belted Tee

Oversized Belted Tee

If you are a fan of oversized tees then this look will definitely be one for you to try.

Oversized belted tee outfits are effortlessly chic when paired with jeans or mini skirts, so why not wear an oversized tee on its own?

Making sure that the tee covers your body, you can make the tee into a mini dress for an easy and stylish look. 

Perfect for the daytime in the summer, add a brown or colored belt to a plain white oversized tee and pair it with trainers or sandals so that you can keep cool during different activities whilst still feeling stylish and comfortable in your outfit.

You can dress the tee up by wearing a summer hat or remain casual with a baseball cap. 

You can also wear the tee out at night as you can easily dress up the look.

Add a black belt to accentuate your body, gold or silver jewelry, and wear with black heeled boots, you already have an effortlessly fashionable look that isn’t uncomfortable or difficult to wear. 

Did you know?

The trend of styling an oversized shirt has roots in the ’80s and ’90s fashion, where the relaxed and effortless aesthetic gained popularity. Today, fashion enthusiasts embrace the oversized shirt as a versatile piece that effortlessly combines comfort with a touch of retro flair, making it a timeless wardrobe staple.

Final Thoughts

Styling oversized shirts can be as casual or as stylish as you want them to be as there are so many different ways of wearing them that you are never limited to just one style.

With so many patterns, lengths, and colors, oversized shirts can add so much fun to your wardrobe and can help you effortlessly style fashionable outfits without feeling uncomfortable whilst wearing them. 

Lots of styles for oversized shirts include showing some skin by unbuttoning the top or bottom buttons of the shirt which is great if you are looking to show some skin, but some may find this too uncomfortable.

If you aren’t a fan of unbuttoning, this isn’t a problem! You don’t have to unbutton your shirts to make them stylish as you can either leave the buttons done up or find another style that suits your needs better. 

The beauty of wearing oversized shirts is that there is a style for everyone and you don’t have to wear anything you are uncomfortable with.

You can pair them with other oversized garments if you want a full oversized look or wear them over tighter clothing to give you some shape. The possibilities are endless!

Oversized shirts are a rarity in the fashion world as they are both comfortable and fashionable, which usually isn’t the case.

A lot of on-trend clothing can be uncomfortable which then affects our confidence, and it is time that these trends disappear.

Oversized shirts allow you to feel confident and beautiful without feeling like you have to compromise on comfort. 

A timeless classic, oversized shirts never go out of style. Wear them with comfort and the knowledge that you look beautiful and stylish for any occasion whilst remaining confident in yourself. 

Brittney Adams

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