How To Wear Oversized Shirts
Reeva Babbar
Table of Contents
How many times have you enthusiastically taken a hand-me-down shirt from your boyfriend, husband, brother, or dad only to realize that you don’t know how to style it right?
Even better, how often did you intentionally buy an oversized shirt after seeing it on a mannequin at the store, only to return it the next day because it didn’t look the way you thought it would?
If this sounds like you, don’t worry. How to wear oversized shirts is a question that troubles many trend-loving individuals like yourself. But learning how to wear oversized shirts doesn’t have to be complicated.
With our expert style tips and advice, we’ll help you style your oversized shirt like a true fashionista. That way, the next time you decide to wear one, you’ll look put together and stylish (and not like a frumpy mess).
Oversized shirts have become a fashion statement in the last decade or so, following the craze over baggy clothes in the ‘90s. Time and time again, people love reaching for clothing that makes them feel comfortable, confident, and maybe even a little bit snuggly.
These spacious shirts provide lots of comfort, so it’s no wonder why so many people love them. Yet, lots of people wonder how to wear these oversized shirts. There are many options available all over social media and the web, which give you lots of style inspiration.
But, with so many confusing style guidelines, it can be hard to determine which style will work best for you. Have no fear: we’ve got all the info you need in this handy guide. We’ve broken down which styles, fabrics, and body-loving oversized shirts will help you create the perfect look for your next #ootd post.
We’ve got all the info you need about oversized shirts. After reading this guide, you’ll understand the following (and so much more!). And you’ll never wonder how to wear oversized shirts again.
- How to wear oversized shirts stylishly
- How to wear oversized shirts with layers
- How to wear oversized shirts without looking fat
What is an Oversized Shirt?
As the name suggests, an oversized shirt is a very roomy, loose-fitting shirt that can hide your curves and also accentuate the lower part of your body. These spacious shirts allow you to style your outfit in a way that looks fashionable and feels comfortable. Oversized shirts hang below the waistline, long past your hips.
Oftentimes, they almost reach your mid-thigh regions, which can give your upper body the illusion of length and a toned structure. Whether you’re pairing it with skinny-fit bottoms or wearing it as a dress, there are so many options for styling them.
Before you can learn about the fashionable ways to wear an oversized shirt, it’s helpful to know where this style came from.
History of Oversized Shirts
Like many fashion trends, the humble beginnings of the baggy shirt started in the 1920s as women were coming around to more relaxed fits.
On the other hand, the trend of oversized clothing for men came more from the hip-hop fashion movement when baggy clothes became new wardrobe-essentials.
Since then, baggy clothes have continued to make a fashion comeback from time to time. The most noticeable comebacks occurred in the ‘80s and ‘90s era when roomy, oversized—and essentially ‘as baggy as possible’—tops, T-shirts, sweaters, and hoodies were all the rage.
These humongous, shapeless shirts became a big fashion trend during one of the most style-significant decades of our time. And now oversized shirts are in style once again.
When it comes to fashion, today’s generation has many ‘90s role models to look up to. So many celebrities are rocking these baggy outfits, which provides style inspiration to many.
How to Choose The Best Oversized Shirts
Of course, styling these loose-fitting shirts properly is a big concern for many. But figuring out how to wear oversized shirts isn’t the only issue.
There are other factors to consider when going to your favorite store to purchase one that works for you. Listed below are some helpful points to keep in mind when choosing your next oversized trend-setting piece:
Price
The price of these roomy shirts depends on what type of look you’re going for when figuring out how to wear these oversized shirts. Many people have a favorite brand that they turn to every time they need an essential item for their closet. So, the price will also vary based on how expensive the clothing label is.
For instance, a simple oversized cotton shirt from H&M will range anywhere from $30 to $35. In contrast, a relaxed-fit longline shirt from Tommy Hilfiger can cost you up to $62 even after the discount is applied.
Of course, when considering how much you’re willing to pay for one of these lounging shirts, the quality of the clothing plays a big role in helping you make your decision.
Quality
When determining the quality of clothing, we often consider how long-lasting it is in terms of wear and tear. Of course, this depends on the quality of the material, which will vary from brand to brand.
So, it’s essential to buy an oversized shirt from a brand that you trust, so you only have to worry about how to wear oversized shirts without worrying about the quality.
As a rule of thumb, go to stores that you’ve tried and tested already, to make sure your items meet your quality standards. Even some brands on Amazon sell excellent quality apparel, and many have amazing return and exchange policies to ensure that their customers are completely satisfied with their products.
Material
As mentioned above, when considering the quality of a piece of clothing the material it’s made of is essential. Before you can learn how to wear oversized shirts, you need to find fabrics that you are most comfortable in.
Some of the best oversized shirts are made of quality, breathable materials, such as cotton, linen, or a mix of cotton with polyester.
Silk is a hit-or-miss type of fabric since it tends to be figure-hugging. So it may or may not be the right choice for you depending on the look you’re going for.
Flannels and plaids are wardrobe staples for many, and they’re usually in fashion during the fall and winter seasons. On top of that, they can make great additions to the oversized section of your closet.
Keep in mind, however, that both of these materials are patterned already, so wearing solid bottoms is essential.
Before you choose a go-to material that you like best for your oversized shirts, it’s a good idea to experiment with a few different fabrics. That way you can see which fit you prefer most based on your body type.
When to Wear Oversized Shirts
Oversized shirts are not associated with one particular event or season. Yet, they’re more appropriate for some occasions more than others. Depending on the style and fabric of the shirt, you can technically wear them during any season.
Despite this freedom, there is a catch: some styles are more popular to wear in certain seasons. For example, sheer and silk tops both look better in the summer and spring months, rather than in the winter and fall. Flannels and plaids, by contrast, look great with fall and winter leggings and boots.
On the other hand, you can wear oversized shirts made of cotton and linen with almost any outfit, no matter what the season is.
When considering how to wear oversized shirts, it’s important to determine which type of outfit will work best for a particular event.
Oversized shirts can be worn in both semi-formal and informal settings and, depending on the cut and style, they can also be worn in a formal business environment.
Most events will have a type of dress code (whether stated or unstated). So when in doubt about what to wear, you can look for outfit inspiration based on the event you’re attending.
If the goal is to have neat and tailored attire though, then oversized shirts are probably a big no-no.
You can, however, pull off an oversized shirt ensemble really well for a casual or even a business casual event since you have the liberty to accessorize and style your loose-fitting, stylish, but comfy shirt. That way you can dress up this casual shirt with appropriate accessories.
Now let’s consider different occasions where oversized shirts will work best. Basically, they can complete and perfect so many looks. So whether you’re spending the day shopping or having a night out with your friends a cute, baggy shirt is a great choice.
There are several ways to style these oh-so-comfy shirts. So, for those who like to experiment with their wardrobe, the possibilities are endless.
Thinking about a nighttime look when out and about in the city? Go for a silk or linen oversized shirt that you can accessorize with a gold or silver designer belt, pair it with black bottoms or wear it as a dress, and match your shoes with your handbag/purse to complete the outfit.
A similar style can be worn as a daytime look, but choose a classic colored belt over a standout one, or wear it without the belt to really showcase your relaxed, effortlessly sexy outfit of the day.
How to Wear Oversized Shirts
When it comes to dressing comfortably, style options are the last thing you should have to worry about. Keep your fashion worries at bay with the following tips and tricks. After reading each one, you’ll know how to wear your oversized shirts stylishly.
Styling advice 101
Try to experiment with fabrics and choose a fit that you prefer when deciding how to wear oversized shirts. If you wish to flaunt your curves, pick an oversized shirt that will cling in all the right places as you move.
If your curves are your greatest concern, look for material that’s more loose-fitting, and will hide the unflattering parts of your body that you’re conscious about.
Wearing it as a dress
Oversized shirts are the transformers of the clothing world. There’s absolutely no need to worry about how to wear oversized shirts because there are so many options. You can wear them as a shirt, an off-shoulder blouse, knotted-up crop top, or even as a dress.
A loose-fitting shirt gives you the liberty to create a dress with your desired length and fit. You can also wear a great pair of leather boots or strappy sandals to complete your perfect, dressy outfit.
Mixing materials/textures
The adventure of creating a perfect look—when thinking of how to wear oversized shirts—often begins by experimenting with different materials.
Of course, the goal is not to mix and match fabrics that are in stark contrast to each other like a flannel oversized shirt with dotted pants, but rather find textures that complement each other, such as a plain, linen oversized shirt with sheer, patterned (dotted or striped) stockings.
Playing with layers
Layering your oversized shirt can be one of the trickiest tasks in your styling routine. The reason for this is that they’re already oversized!
Finding layering techniques for these comfy fits becomes especially important when the weather is a bit chilly though (and uncooperating with your trendsetting dreams).
Thankfully, there is a solution. Try pairing an unbelted, oversized shirt with a short, fitted leather jacket or mid-thigh length fitted coat. Also, belted shirts look great with long parkas and blazers.
5 Outfit Ideas with Oversized Shirts
The model above is wearing an oversized, white cotton shirt (the Mika Anine Bing Shirt).
She compliments her loose-fitting shirt with Anine Bing Jagger Jeans and faded, black suede Isabel Marant Chaussures Boots. She’s also wearing black and white, square sunglasses that match the classic tones of her outfit.
To bring a bit of contrast to her outfit, which includes black and white symmetry, she is carrying a tan, Marie Turnor Lunch Clutch.
The beauty of this ensemble lies in the simple, yet classic tones of the top and the bottom.
The oversized cotton shirt flows neatly over the skinny-fit jeans, and the small, stiletto-heeled boots provide some length to the overall look. There is a fashion go-to when styling free-flowing cotton oversized shirts. It’s best to wear figure-hugging bottoms, especially if your goal is to look slimmer.
A crisp, white cotton oversized shirt is styled with a beige sweater-vest by this model. The oversized shirt transforms into a dress with the large gold-buckled, black belt that matches her knee-length boots.
There is one highlight of this oversized shirt dress: the similarity between the loose-fitting cotton shirt and the relaxed-fit sweater vest. Both of them are tucked in perfectly using a belt that provides shape and structure to the model’s silhouette.
This is a great way to wear layers without making your outfit look too bulky. Try to include layers that hold your look together, by synching in the fabric under the bust, which will accentuate your curves in all the right places.
The model above is wearing a green oversized shirt known as the Karma Lover Oversized Shirt from Halite Clothing. The shirt is made of cotton and polyester, and she’s wearing it unbuttoned with a white crop top and light sky-blue shorts.
The light blue color of her shorts matches her light blue sandals and soft white handbag perfectly.
Oversized shirts are often worn buttoned down. If you’re going for a more relaxed look, try leaving your baggy shirt unbuttoned and wear it over your fitted, summer outfit.
To complete the ensemble, pair it with your favorite summer sandals or wedges for a relaxed and stylish look.
The model above is styling a ruffled, buttoned-down, white oversized shirt. It makes a perfect dress for a night out with friends or a date night with your bae.
The outfit is enhanced with her pointy, polished, clear heels and chunky, bronze hoops. And the whole look comes together with her hair that’s neatly tied into a low bun.
The ruffles on this soft, white, oversized polyester shirt are a nice feminine touch. The no-stretch material makes it the best figure-hugging outfit that enhances the body’s curves in all the right places.
Also, the heels dress up the outfit a bit, creating a more formal style. So this trendy, party look can be achieved with minimal effort.
This model is wearing a white, oversized shirt with ripped skinny-fit jeans. She styles this look by layering a cropped, black leather jacket over her loose-fitting shirt.
This casual look is supported by the black slip-on runners, a side sling laptop bag, and black translucent glasses.
Leather jackets are a great way to layer your oversized shirts because they’re usually slim-fitting by nature. This provides the perfect cover if you’d prefer a more fitted, polished look.
There’s one thing to keep in mind when styling a leather jacket with an oversized shirt: make sure that the length of the jacket doesn’t sit aligned to the length of the shirt. This is a big faux pas because your outfit will look too bulky (rather than your desired slim fit).
How to Wear Oversized T-Shirts: Guys
Although this guide is focused primarily on women, the information about how to style oversized shirts is applicable to men as well.
Here’s a general rule of thumb for deciding on how to wear oversized t-shirts guys edition: the contrast of a baggy top with fitted bottoms is a great choice for most casual settings.
The only exception to this rule is when you’re wearing comfortable, slightly loose-fitting jeans that sit at the ankles. These jeans are the perfect length and fit for when you want to wear an oversized T-shirt. This outfit creates an ultra-stylish look without compromising comfort.
Fashion Tips to Avoid With Oversized Shirts
Figuring out how to wear oversized shirts really isn’t complicated. But there are some things to avoid when styling these shirts. We’ve written a few tips for you below.
- Depending on the design, some clothing will fit differently compared to others made of the same fabric. So, when considering how you want the oversized shirt to sit on your body, it’s important to keep this in mind.
- Though it often works against your look, you can layer your oversized shirt with a jacket of similar length. But, as always, it’s best to try out a look on your body before writing it off.
- If wearing your oversized shirt as a dress, you don’t always have to wear heels or boots. Some formal flats, slip-ons, sneakers, high-tops, and even kitten-heeled flip flops make trendy pairings with your oversized shirt dress.
How To Take Care Of Oversized Shirts
As a rule, oversized shirts are both lengthy and loose-fitting. So, taking proper care to wash, dry, and/or iron these roomy shirts is essential to keep them looking fresh and new in your wardrobe.
Always read the clean and care instructions on each shirt label to ensure that your top won’t shrink and that proper care is maintained.
Best Places to Buy Oversized Shirts
These loose-fitting shirts are available at almost any retail store, since they’re quite popular and very much in fashion today. Some of the stores mentioned in this guide carry a good selection of them with a wide range of colors and styles, such as H&M, Tommy Hilfiger, Amazon, and Halite Clothing,
Along with these options, you can find a range of affordable styles for oversized shirts in Ardene, Banana Republic, Zara, and The Bay, to name a few.
Final Thoughts
Oversized shirts have become a way for men and women to wear a relaxed, comfortable, yet trendy outfit. As already mentioned, these shirts first became popular in the ‘20s and continue to be around decades later.
They really have become a wardrobe staple for many, and are go-to attire when you want to wear a classic, yet fashionable look.
With their popularity in full gear, it’s important for consumers like yourself to shop for the best price, quality, and material you can find. That way you can pull off this trendy look with confidence and flair, and make sure your roomy shirts last the long term.
The outfit ideas and inspirations provided in this guide give you an opportunity to explore different options for wearing your oversized shirts—whether you’d prefer to wear them as a dress with knee-length boots or with layers and fitted pants.
Of course, many of these ideas are also applicable to men when they want to look stylish wearing oversized T-shirts.
The key element to keep in mind when styling your oversized shirt is to think of your purpose behind wearing them. If your purpose is to hide your curves, then wear fabrics and materials that are more breathable as opposed to slim-fitting linens and silk.
Above all, have fun and experiment with various fits and styles at your favorite retailers to find one, two, or more to bring home and add to your trendy closet.
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