How To Style An Oversized T Shirt: 4 Chic Looks To Try For Men

how to style an oversized t shirt

The oversized t-shirt trend has taken the fashion world by storm, gracing runways and Instagram feeds alike. But if you’re a guy who’s used to the snug fit of your favorite tees, knowing how to style an oversized t shirt can feel like uncharted territory. 

Fear not, because in this guide, we’ll walk you through four effortlessly chic ways every man can master. Whether you’re aiming for a classic, casual, or cutting-edge look, we’ve covered you with expert fashion tips and inspiration. 

So, let’s unlock the secrets to rocking the oversized tee trend with confidence and style!

Finding the Right Fit: What Makes an Oversized T-Shirt?

Before diving into styling, it’s crucial to understand what makes an oversized t-shirt truly oversized. It’s not just about grabbing your regular tee in a size too big; that often leads to an unflattering, long, and narrow look. 

Instead, look for t-shirts intentionally designed to be worn oversized. Watch for words like “oversized” or “relaxed” when shopping. Here’s what to look for:

Looser Fit

The t-shirt should fit looser around your torso and sleeves than your regular tees. However, the length of the T-shirt doesn’t need to be excessively long. It can range from hip level to slightly below your crotch.

Consider cropped oversized tees for a standard length, which you can tuck in if desired.

how to style an oversized t shirt

Sleeve Length

Opt for sleeves that extend below mid-bicep length but stay above the elbow.

Avoid extremes in sleeve length, as maintaining a balanced appearance is key to nailing the oversized look.

Drop Shoulder

Seek t-shirts with a slightly dropped shoulder seam. This detail complements the oversized style and adds a touch of laid-back elegance.

Weighty Fabric

Select t-shirts crafted from heavyweight fabric to provide structure and achieve a boxy fit.

Lightweight cotton won’t cut it; you want a fabric with a substance that allows your oversized tee to sit nicely on your body.

How To Style An Oversized T Shirt for Men

Styling an oversized t-shirt begins with understanding what truly defines an oversized fit. It’s not merely about opting for a larger size of your regular tee; that often results in an unflattering appearance with excessive length and a narrow silhouette.

Here’s a breakdown of how to style an oversized t shirt:

White Top, Slim Bottom Combo

Embrace a classic style reminiscent of 2015 Harry Styles. Pair your oversized tee with slim-fitting bottoms for a stylish contrast. Here’s how to achieve this look:

Styling Tips:

  • Choose slim-fit jeans or trousers to create a streamlined lower half.
  • Opt for boots to elongate your legs rather than low-top sneakers.
  • Consider a shorter jacket or a cropped one to let the t-shirt extend below it, or go for a long coat to emphasize the top-heavy look.

This silhouette offers a rocker or grunge vibe and works wonders in elongating your legs, especially if you’re on the shorter side. Keep in mind that it’s most flattering on slimmer body shapes.

how to style an oversized t shirt

Relaxed and Slouchy

For a laid-back yet chic appearance, go for the “off-duty celeb” vibe. The relaxed and slouchy style is forgiving on all body shapes. Here’s how to master it:

Styling Tips:

  • Pair your oversized tee with relaxed joggers or relaxed-fit jeans.
  • Aim for a slouchy yet chic look by incorporating interesting patterns, clean, well-ironed clothes, and subtle jewelry like necklaces, bracelets, or rings to elevate the outfit.

This style is all about looking effortlessly cool while maintaining a relaxed aesthetic.

The Hourglass Look

Emphasize both your upper and lower body with this flattering style. Create an hourglass figure by cinching your waist while keeping the oversized tee. Here’s how:

Styling Tips:

  • Choose straight-legged trousers with a regular to wide fit.
  • Tuck your oversized tee into your pants to define your waist.
  • Opt for chunkier shoes to add weight to the lower half.
  • Consider clean-looking trousers with a pressed crease for a Scandinavian chic vibe.

Add a shorter jacket to maintain the hourglass silhouette.

This style complements various footwear options, from slim minimal sneakers to chunky ones, allowing you to adapt it to your style.

The Structured Oversized Look

Achieve an oversized silhouette with a touch of structure by following these styling tips:

Styling Tips:

  • Pair your oversized tee with smart trousers that can have some tapering from the knee down.
  • Consider a cropped hem on your trousers for a clear delineation between them and your shoes.
  • Footwear options vary from slim minimal sneakers to chunky sneakers, derbies, or boots.
  • Opt for a shorter jacket or a long coat based on your preference.

This versatile silhouette provides flexibility in styling your oversized t-shirt, allowing you to adapt it to your unique aesthetic.

how to style an oversized t shirt

Common Mistakes To Avoid When Styling An Oversized T-Shirt

Styling an oversized t-shirt can be a great way to achieve a relaxed and fashionable look, but guys often make some common mistakes when doing so. 

Avoiding these pitfalls will help you pull off the oversized t-shirt trend effortlessly. Here are some mistakes to steer clear of:

Choosing the Wrong Size

Perhaps the most common mistake is selecting an oversized t-shirt that is too large. Remember, oversized doesn’t mean you should wear a tee multiple sizes too big. The fit should be comfortably loose without drowning you in fabric.

Ignoring Proportions

Failing to balance the oversized top with the rest of your outfit is a common mistake. To avoid this, ensure that your bottoms, whether pants or shorts have a slimmer or more tailored fit. This contrast will create a stylish, well-proportioned look.

Neglecting Tailoring

Not all oversized t-shirts will fit perfectly off the rack. If your tee has excessively long sleeves or is too long overall, consider getting it tailored to achieve the right fit. A well-fitted tee will always look better.

Overlooking Fabric Quality

Opting for flimsy, low-quality fabric can make your oversized tee look cheap and shapeless. Choose t-shirts made from heavyweight or high-quality materials that provide structure and drape nicely on the body.

Neglecting Accessories

Accessories can elevate your oversized t-shirt outfit. Don’t forget to add details like a stylish belt, a watch, or sunglasses to complete your look. These small touches can make a big difference.

how to style an oversized t shirt

Mismatching Footwear

Pairing your oversized tee with the wrong shoes can destroy the entire outfit. Avoid overly bulky or chunky footwear, as it can make you appear unbalanced. Instead, wear sleek sneakers, boots, or loafers to maintain a cohesive look.

Ignoring Occasion

Oversized tees may not be suitable for all occasions. Wearing one to a formal event or a business meeting is generally not advisable. Consider the dress code and appropriateness of the oversized tee for the specific occasion.

Overdoing Layer

Layering can work well with oversized tees, but it’s easy to overdo it. Adding too many layers, like multiple jackets or vests, can make your outfit appear cluttered. Please keep it simple and focus on one or two complementary layers.

Neglecting Grooming

Pay attention to personal grooming when wearing an oversized tee. A well-groomed appearance, including neatly styled hair and good personal hygiene, can enhance your overall look and prevent a sloppy appearance.

Following Trends Blindly

While staying fashion-forward is essential, unthinkingly following trends without considering your style and comfort can lead to fashion disasters. Choose oversized tees and styles that resonate with your taste and make you feel confident.

Styling an oversized t-shirt for guys requires a balance between comfort and fashion. Avoiding these common mistakes will help you achieve a stylish and well-put-together look while embracing the oversized trend.

how to style an oversized t shirt


How Do You Style An Oversized Shirt Professionally?

Styling an oversized shirt professionally involves achieving a balanced and put-together look. Here are some tips:

  • Tuck in your oversized shirt to create a neater appearance and define your waist.
  • Pair it with well-fitted trousers or slacks for a sleek and polished look.
  • Choose a belt that complements the outfit and adds a touch of sophistication.
  • Opt for dress shoes or loafers to complete the professional ensemble.
  • Consider adding a blazer or structured jacket for a more formal touch, ensuring it complements the oversized shirt.

Which Type Of Pant Goes With Oversized T-Shirt?

Oversized t-shirts can be paired with various types of pants depending on the style you want to achieve. Here are a few options:

  • Slim-fit or tapered trousers: These provide a clean and balanced look, contrasting the relaxed fit of the oversized tee.
  • Wide-leg pants: Pairing your oversized shirt with wide-leg trousers can create a fashionable, street-style-inspired outfit.
  • Tailored dress pants: Consider combining your oversized tee with well-tailored dress pants and dress shoes for a more formal appearance.

Which Type Of Jeans Goes With Oversized T-Shirt?

When pairing oversized t-shirts with jeans, consider the following options:

  • Straight-leg jeans provide a classic and balanced look when worn with an oversized tee. The straight cut complements the loose fit of the shirt.
  • Relaxed-fit jeans: These jeans offer a laid-back, comfortable style that pairs well with an oversized t-shirt.
  • Wide-leg jeans: For a fashion-forward and bold look, opt for wide-leg jeans to create a unique contrast with your oversized tee.

Is Oversized T-Shirt Good For Skinny Guys?

Yes, oversized t-shirts can be a great choice for skinny guys. The relaxed fit of an oversized tee can add volume and create the illusion of a more substantial physique. 

However, finding the right balance is essential to avoid looking overwhelmed by the oversized fit. Choose an oversized shirt that fits the shoulders and sleeves well, ensuring it doesn’t appear too baggy. 

Experiment with different styles and accessories to create a flattering, stylish look that suits your body type and personal preferences.


How to style an oversized t shirt is no longer a mystery. With our guide to 4 chic looks, you now have the fashion keys to unlock a world of possibilities. Embrace the classic, the relaxed, the hourglass, or the structured appeal—the choice is yours. 

These versatile styles prove that oversized tees aren’t just comfortable and a canvas for your personal expression. So, experiment and let your wardrobe reflect your evolving style, one oversized t-shirt at a time.

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