2023 Guide: How to Wear Oversized Shirts for Men

Are you ready to upgrade your fashion game? Oversized shirts for men are a versatile and trendy addition to any wardrobe.

In this comprehensive guide, we will explore how to wear oversized shirts for men and provide ten engaging headings and subheadings that cover everything you need to know.

Oversized shirts are in style, but some people are hesitant about wearing them because they can appear bulky and unflattering. Fear not, by following these tips, you will be able to rock oversized shirts with confidence.

Here are some key points to keep in mind when wearing oversized shirts:

1. Stick to the Right Fit

Oversized shirts should still fit you in a flattering way. When shopping for one, look for a size that is larger than your usual fit but still suits your body shape.

The oversized shirt should be loose but not too baggy. You want to avoid looking shapeless, so make sure that the shirt still has some structure.

2. Pair it with Fitted Bottoms

Since the oversized shirt is larger, it’s essential to pair it with well-fitted bottoms. This will balance out the look and prevent the outfit from looking frumpy.

Skinny jeans or slim-fit trousers are perfect for this kind of outfit. The aim is to create a proportionate silhouette that is pleasing to the eye.

3. Accessorize Wisely

Accessorizing with the right items can elevate your oversized shirt outfit. Consider adding a belt to create a more defined waistline.

Bold statement jewelry also works well to add a pop of color and personality. Remember, accessories are the icing on the cake and can make all the difference in an outfit.

4. Experiment with Layering

Oversized shirts are perfect for layering. You can wear them over a t-shirt for a more relaxed look or under a structured jacket for a smart-casual outfit.

Layering will add depth to your outfit and keep you looking stylish throughout the seasons.

5. Know Your Fabrics

Choosing the right fabric is crucial to nailing the oversized shirt look. Cotton and linen are both ideal for a casual daytime outfit, while silk and viscose are perfect for an evening look.

When it comes to choosing the fabric, consider the occasion, weather, and the overall vibe you want to achieve.

6. Roll Your Sleeves

This simple trick can make a massive difference in your outfit. Rolled sleeves will add a touch of nonchalance to your outfit and prevent your oversized shirt from looking too bulky.

Avoid folding sleeves too much, and keep them loose for an effortless vibe.

7. Play with Prints

Who says oversized shirts should be boring? Experiment with prints and patterns to add some interest to your outfit.

Floral, stripes, and plaids are great options to try. Be sure to keep your bottoms neutral to balance out the prints.

8. Embrace Monochromatic Outfits

If you’re looking for a foolproof way to wear oversized shirts, try monochromatic outfits. This means pairing an oversized shirt with matching pants or shorts.

A single color palette will create a cohesive look that is both trendy and polished.

9. Tuck it in or Leave it Out

The good news is you can wear oversized shirts tucked in or left out, depending on your preference. Tucked-in shirts create a more polished and put-together look, while leaving it out gives off a casual and relaxed vibe.

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Try both and see which one suits your style and occasion better.

10. Confidence is Key

At the end of the day, the most crucial factor in pulling off any outfit is confidence. Own your style, and don’t be afraid to experiment.

Trust your instincts and wear what makes you feel good. Remember, fashion is an expression of yourself, so have fun with it!

According to the search results, oversized shirts for men are a must-try trend. Celebrity fashion icons, like Kanye West and Justin Bieber, have been spotted wearing oversized shirts and nailing the look.

With the right fit, pairing, and accessorizing, anyone can rock an oversized shirt and feel confidently stylish. By following these tips, you can elevate your outfit game and master how to wear oversized shirts men.

Check out this Youtube video: “Casual Luxury: How to Wear Oversized Button Down Shirts,” for useful tips on how to rock oversized shirts in style specifically for Men’s Clothing enthusiasts.


When it comes to oversized shirts for men, choosing the right fit is crucial. A shirt that is too loose or too tight can completely ruin the look.

The ideal fit is one that is slightly oversized and falls just below the waist, giving a relaxed but polished appearance. It’s also important to consider your body shape.

If you’re on the shorter side, opt for a shorter length shirt to avoid overwhelming your frame. If you’re taller with a broad chest, choose a shirt with a more generous cut to avoid looking like you’re squeezing into a shirt that’s too small.


The perfect length of an oversized shirt is crucial when it comes to styling. According to Flex Your Idea, men should aim for a length that reaches mid-thigh when paired with slim jeans or trousers.

If opting for shorts, the shirt should sit slightly above the knees. This simple rule ensures a balanced and stylish look that will turn heads.

an image of a man wearing an oversized shirt that is too long for his proportions - how to wear oversized shirts men

Essentials in Your Wardrobe

When it comes to wearing oversized shirts for men, it’s important to have essential pieces in your wardrobe to complement this relaxed style. Firstly, a pair of tailored trousers or fitted jeans can add structure to the outfit, balancing out the loose fit of the shirt.

You can also opt for shorts or joggers for a more casual look. Secondly, accessorizing with a belt can cinch your waistline, creating a more defined silhouette.

A hat or cap can also add a touch of personality to the outfit. Lastly, footwear plays a big role, and you can choose between sneakers, loafers, or boots to complete the look.

By having these essentials in your wardrobe, you can effortlessly rock the oversized shirt trend while still looking put together.

Outfit Ideas

a. Styling Oversized T-Shirt with Long Working Pants

If you’re wondering how to wear oversized shirts men to work or casual meetings, simply pair them with long working pants for a polished and put-together look. According to www.masterclass.com, wearing oversized shirts with snug-fitting jeans can create a balanced and effortless look.

To make it more work-appropriate, choose long trousers in a solid color like black, navy, or gray. You can also experiment with different colors and prints for the shirt, but make sure to keep the pants neutral to avoid clashing.

Don’t forget to tuck in the shirt and add a belt for a more polished finish.

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b. Styling Oversized T-Shirt with Shorts

To create a casual and relaxed look with your oversized t-shirt, try pairing it with shorts. Masterclass suggests pairing formfitting blue jeans such as straight-leg or skinny jeans with an oversized shirt for a chic and effortless ensemble.

For a minimalist look, consider a long-sleeved white shirt with white shorts, creating a stylish and understated monochromatic outfit. Complete the look with some sneakers for a comfortable yet fashionable summer look.

Don’t forget to tuck in your shirt to accentuate your waist and avoid looking too baggy.

Styling an oversized t-shirt with jogger pants is a great way to create a comfortable yet stylish outfit for casual occasions like dates or chillaxing sessions. According to Masterclass, one way to flaunt an oversized shirt is by pairing it with form-fitting jeans, such as skinny or straight-leg jeans, to create a balanced and relaxed look.

Another option is to go for a minimalistic monochrome style with a long-sleeved white shirt and white jeans. You can also add sneakers to complete the look.

Creating an effortless, laid-back vibe is key when styling an oversized t-shirt with jogger pants.

d. Styling Oversized T-Shirt with Jeans

One great way to wear an oversized shirt for casual occasions is to pair it with a well-fitted pair of jeans. According to Masterclass, a great approach is to opt for jeans with a straight-leg or skinny cut.

This can help balance the oversized shirt and give off an effortlessly relaxed vibe. For a clean, minimalist look, try pairing a long-sleeve white shirt with white jeans.

This monochromatic look is perfect for any casual occasion. With the right styling, oversized shirts can be a versatile addition to any wardrobe.

How to Wear Oversized Shirts Men

Wearing oversized shirts can be a stylish way to switch up your look, but it can also be a tricky trend to master. Here are some tips to wear oversized shirts for men:

  • Balance the volume: Oversized shirts are already bulky, so pair them with slim-fit pants or shorts to avoid looking too boxy.
  • Half tuck: Tucking in just the front of an oversized shirt can create a relaxed and stylish look.
  • Layering: Layering an oversized shirt with a fitted jacket or cardigan can create dimension and a polished look.
  • Accessorize: Add accessories such as a belt or statement jewelry to create a focal point and add structure to your outfit.
  • Play with patterns: Experiment with bold patterns or prints on oversized shirts to make a statement.
  • Experiment with different materials: Try different materials such as denim, flannel, or linen to create different moods and textures.

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man wearing oversized shirt with slim pants and leather shoes - how to wear oversized shirts men

man layering oversized shirt with fitted cardigan - how to wear oversized shirts men

Historical Facts

Oversized shirts have been in style for men since the 1920s when the “flapper” look was popular for women. Men began wearing shirts that were not form-fitting and had a loose silhouette.

In the 1970s, the “hippie” fashion emerged, and loose-fitting clothing was trendy again. Oversized shirts also became a favorite of the grunge style in the 1990s, and now oversized shirts are a fashion staple for men.

The oversized shirt trend has also grown in popularity due to the rise of streetwear fashion.

Quality over Quantity

Investing in high-quality oversized shirts can make a huge difference when it comes to elevating your style. While it might be tempting to opt for cheaper, low-quality options, premium oversized shirts offer better fit, durability, and overall appearance.

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Look for shirts made from quality fabrics like cotton, linen, or silk, and consider brands that specialize in oversized or relaxed-fit clothing. When shopping for quality oversized shirts, pay attention to details like stitching, buttons, and overall construction.

A well-made, quality shirt will not only help you look your best, but it will also last longer and save you money in the long run.

Grooming and Accessories

If you want to elevate your oversized shirt outfit, you can add accessories to make it more stylish and interesting. Consider wearing a pair of sunglasses to complete the look.

Choose a simple and classic style like aviators or wayfarers.

As for grooming, keep your hair neat and styled. A simple hairstyle like a slicked-back or messy top knot can complement the effortless vibe of an oversized shirt.

Trim your beard or mustache, and keep your skin looking fresh with a good skincare routine.

To keep the focus on your oversized shirt, choose minimalist accessories and natural-looking grooming. This way, you can still look put-together without overpowering the outfit.

Remember, less is more!

Mistakes to Avoid

When wearing oversized shirts, men often make common mistakes that can ruin their overall look. One such mistake is choosing the wrong size of shirt.

It is important to remember that oversized does not mean ill-fitting. Another mistake is wearing the wrong bottoms.

It is best to pair oversized shirts with slim-fit or straight-leg pants. Avoid wearing baggy pants or shorts.

Tucking in the oversized shirt is also a common mistake. The shirt should be worn untucked or partially tucked for a casual look.

Lastly, wearing too many layers with the oversized shirt can make the outfit look bulky. It is best to keep it simple and pair the shirt with minimal accessories and clothing items.


Oversized shirts are versatile and comfortable clothing options that men can experiment and have fun with. To wear them stylishly, make sure to balance the fit by pairing them with either slim-fit bottoms or structured jackets.

Play with textures, patterns, and accessories to elevate your outfit. Additionally, oversized shirts can be worn all year round, with appropriate layering in wintertime and without compromising comfort in summer.

As with any fashion advice, make sure to wear what makes you confident and comfortable.


Frequently Asked Questions

Is it OK for men to wear oversized shirts?

Yes, oversized shirts give off their own chic and edgy look while providing comfort and versatility.

What do you wear with an oversized shirt?

Oversized shirts can be stylish when paired with blazers and track pants. For a sophisticated look, tuck them into a denim skirt or shorts. You can also wear them as a dress or with a belt for a modern chic look.

Can skinny guys wear oversized shirts?

Yes, but be careful to find the right fit. Avoid completely skin-tight clothes and baggy outfits. Find clothes that fit nicely and add them to your wardrobe.

How to layer oversized t-shirt men?

There are many ways to layer an oversized T-shirt. For example, layer it with another T-shirt, a checkered shirt, or a denim jacket. You can also go for a plain and simple look or add a short jacket or a lengthier coat for a cool style.

Jonathan B. Delfs

I love to write about men's lifestyle and fashion. Unique tips and inspiration for daily outfits and other occasions are what we like to give you at MensVenture.com. Do you have any notes or feedback, please write to me directly: [email protected]

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