Oversized t-shirts might not be new on your radar, but they’re certainly back for another season. Throw on this easy-to-wear t-shirt for fresh summer ‘fits, and comfy loungewear looks, the oversized t-shirt is a staple for any man’s wardrobe.
It’s all about the silhouette with oversized t-shirts for men, and considering all the little details like the length of the tee, width, and sleeve length. The aim isn’t to be swamped in excess fabric, but for your oversized t-shirt to fit your proportions, just with a baggier cut.
Oversized tees are so popular because they’re comfortable, stylish, and versatile. You can wear them to work out in, nothing beats a classic cotton tee sometimes for a comfy workout ‘fit. Style them with your favorite sweatpants or lounge shorts for trendy athleisure wear looks that offer the ultimate comfort whether you’re heading to the airport or taking a rest day.
But if there’s anywhere the oversized trend has made a stamp it’s the fashion world. Baggy tees have become the foundation of stylish and statement ‘fits, paired with slick tailored cuts, slouchy denim, boxy collared jackets, and even baggier pants.
An oversized t-shirt outfit can be made simple, street, stylish, or sophisticated, whatever it is; discover how to style oversized t-shirts for men in our ultimate guide to shopping oversized.
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What Style Oversized T Shirt Should I Get?
It’s not just one-size-fits-all, oversized t-shirts are available in numerous popular styles for classic and trendy outfits. Find your favorite…
Types Of Oversized T-Shirts
Heavyweight t-shirts are the in-shirt of the season for guys, known for their structured cotton silhouettes and premium feel, we just can’t get enough of them, and neither can you. These weighty numbers are an easy way to elevate a simple t-shirt and shorts outfit, and they can look extremely fashionable when styled with the correct accessories like cargo pants, heavyweight hoodies, and relaxed tailoring.
Now for the crem-de-la-crem of oversized t-shirts, the graphic vintage tee. They’re the prized possession of any second-hand shoppers closet, the product of hours spent peeling through racks at the thrift stores. Characterized by their dark vintage wash, edgy band logos, or retro designs, oversized graphic tees are the perfect choice for men’s casual dressing - no matter your style. They look great with all-black outfits, light baggy denim, cargo pants, slim-fit jeans, or sweat shorts for a laid-back loungewear style.
Why not shop our Graphic T-Shirts? Not as old as your dad, but probably cooler.
One way to make styling oversized t-shirts easy for guys is to ensure you have a plain white oversized tee. This closet essential will go with everything in your wardrobe, whether that’s subtly showing a corner of the tee layered underneath a cozy sweater or a pair of fresh summer shorts and matching box white sneakers. We love the fit of a baggier tee for a more relaxed and comfy feel. The classic white tee makes for the perfect layering piece to wear under open shirts and jackets to add a pop of brightness to the outfit.
Men’s cropped shirts have risen in popularity over recent years, and before you get the wrong idea, we do not mean the belly-button baring crop tops (although props to you if you can pull one off). Let's call them the slightly cropped t-shirt, as the crop is just meant to be an inch or two off the regular length so the t-shirt sits nicely just above the waistband. These boxy-fit oversized t-shirts are the silhouette of the season, bang on trend, and perfect for laid-back baggy 'fits when paired with slouchy jeans or jorts. They’re also great for guys who are trying to balance their proportions, as the cropped fit gives the appearance of longer legs.
We like to keep our gym shirts separate from our regular clothes (especially for wash days), however, sometimes our everyday styles cross over into gym territory, and the oversized silhouette feels just as at home at the squat rack as it does on our rest days. An oversized gym shirt will do the trick for days in the gym where you want to feel comfy and wear something a little looser. Baggy cotton tees are great to wear with men’s gym shorts for lifting in or LISS sessions on the machine, but if you’re doing any exercises with bends, jumps, or folds, you might want to wear something more form-fitting.
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How To Wear Oversized T-Shirts For Guys
Looking for inspo on what to wear with your oversized t-shirts? We’ve got simple yet effective items to pair with your baggy tees, guaranteed to hit the mark, every time.
With Shorts
Summer is here, and that means guys are searching for comfy, cooling, lightweight outfits to keep you looking and feeling fresh in the warmer weather. Whether you’re heading to the gym or dressing for casual daily ‘fits, oversized tees with shorts are an easy pairing that everyone looks good in. We’d opt for an oversized tee that falls just below the waistband when wearing shorts, as the shorter length of pants allows you to go longer on top. Whether it’s hoochie daddy shorts, breezy bball style mesh shorts, cargo shorts, or trendy long-line denim, you can achieve a stylish look when you pair them with an oversized t-shirt. Pull your crew socks up and pair them with your favorite summer sneakers or choose a comfy pair of sandals to complete the look.
With Jeans
We all have our favorite pair of jeans; baggy, slim, bootcut, or skinny. Whatever cut is your fit of choice, it’s good to know what top looks best with them, and to get the oversized t-shirt look right, the style of denim is make or break.
So what jeans look best with oversized T-shirts? As we all know, baggy jeans are in, so if you want to wear a looser style, stick to less structured denim for an effortless, slouchy, relaxed look or a more sturdy pair for workwear ‘fits. Men can pair their jeans with a slightly cropped t-shirt to balance the silhouette. You can also use your jeans to add balance and dimension by wearing fitted denim with a baggy top, it’s a slightly less modern outfit formula but is still a style that works. The only caveat is that we’d avoid super skinny jeans as the contrast can look extreme with an oversized tee.
With Cargos
An oversized tee can be a statement itself, but the bottom half of the outfit is also important to creating the overall vibe of the outfit. For aesthetic, trendy outfits for men, you can rarely go wrong with a pair of cargo pants. The utility trousers come in baggy and slimmer-fit silhouettes, with each option achieving a different look. Baggy cargos create a relaxed and modern look paired with an oversized t-shirt and intentionally hit the sweet spot of slouchiness without looking scruffy. Alternatively, slimmer fit cargo such as cargo joggers creates a sportier, more classic look suitable for the gym or athleisure style outfits.
With Loungewear
Oversized t-shirts for guys are a staple of streetwear, and always work well for casual occasions, and for leisurely outfits that you feel your best in. Pair them with straight-leg sweatpants, high-top sneakers, and a baseball cap for an effortless urban look. Choose well-placed graphics or smaller logos on your oversized tees to achieve that low-key yet stylish streetwear vibe.
The humble hoodie has a place in every man’s closet: from yogis to lifters, actors to athletes, the oversized hoodie has become a symbol of effortless style. Wear yours over a baggy t-shirt for ultimate layering. Pair with sweatpants and relaxed sweat shorts perfect for your lounge days, or comfy travelling outfit. With the added wiggle room for your torso and arms, the more comfortable you’ll feel, especially if you’re sat in one place for a long time, or trying to settle into a cozy lounging position… the roomier the better!
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What To Consider When Shopping Oversized
For guys, getting the right oversized t-shirt is all about the silhouette of the garment, and what you pair with them. Discover how your baggy tees should fit and how you can create dimension, interest, and balance in an oversized t-shirt outfit.
How Should An Oversized T-Shirt Fit?
When it comes to oversized fits, it's important to note that while they are designed to be roomier than a regular-fit shirt, they should still be your actual size. The intention is for them to have a loose fit, not to swamp you with excessive fabric. Instead, they should have a deliberate roominess to create a boxy and well-proportioned look. Generally, an oversized tee will have a broader cut, with a baggier fit around the torso and sleeves, and drop shoulders for a more relaxed appearance and slouchier ‘fit.
Keep in mind that the length of the tee can vary depending on the look you're going to. For a longer fit, it should fall just below your waistband to the top of your thigh, or for a slightly cropped, boxy fit, you’ll want the seam to sit just around your waistband. Sleeve lengths tend to sit further down your arm nearer your elbow than regular-fit t-shirts, allowing for a lot of movement in the upper body.
Did we mention oversized t-shirts are great for enhancing the size of your chest and shoulders, and even your back? Special mention to the Power T-Shirt which is designed with a wordmark logo that stretches over the curves of your upper back muscles to make your back appear wider.
Consider Proportions
When it comes to oversized, it’s all about getting the proportions right. Baggy clothes can be challenging to style if the proportions are off. The length of your oversized shirt, for instance, is important to consider when building a baggy t-shirt outfit. If you’re going for an oversized everything look, you might want to pick a slightly shorter tee with a boxy fit that creates some shape and dimension when paired with baggy trousers. Tapered bottoms also work if you want to go baggy on the legs but avoid looking like a sack of potatoes. Contrastingly, the rule when it comes to more fitted pants is to not go too skinny, to avoid the popsicle look.
Create Balance
Similar to considering the proportion of your oversized t-shirt, it’s also important to add balance to your outfit to make it look more fashion-forward, and less faux pax. Adding balance to an outfit can look like adding slimmer-fit elements to the outfit, like pairing your oversized tee with slim-fit jeans, or tapered joggers. Another way to do this is to mix and match casual and smart pieces such as pairing your oversized tee with some tailored trousers, or a smart structured coat for some contrast. Being intentional with how you wear your oversized t-shirts can add balance and interest to an outfit.
FAQs
Oversized t-shirts are best to wear in casual settings, particularly places that have a relaxed dress code or don’t require one at all. They can be worn to the gym, run errands, lounge in, travel in, or for leisurely activities such as a Sunday coffee run.
Loose styles look best when worn with other casual pieces, although they can definitely be dressed up and paired with contrasting items like tailored pants and jackets. But generally, we wouldn’t recommend wearing oversized t-shirts in formal or business settings.
However, if you’d like a challenge and you enjoy the comfort a baggier t-shirt provides, you can certainly make them smarter by pairing them with overshirts, dress pants, and elevated accessories.
When shopping oversized it’s important to consider that the goal is for the garment to fit relaxed and comfortably, not baggy or ill-fitting. This means, if a t-shirt is already labeled oversized, then you should pick your regular size. You won’t achieve the same look by just sizing up in a regular t-shirt as the proportions aren’t designed with the same width, sleeve length, and t-shirt length in mind as an oversized tee.
Preference does come into play here, and many prefer to achieve an even more baggy look from their garments. If you want the tee to have a looser fit around the waist, a longer fit than a typical t-shirt, or even longer sleeve length, you may want to go up a size or two larger than your regular size. It also depends on the specific style of the t-shirt and desired aesthetic, for example, heavy-weight oversized tees are designed to fit structured and boxy on the body, so sizing up too much in this style of tee might create an odd and imbalanced silhouette.
Final Thoughts
Oversized t-shirts have firmly established themselves as a staple in men’s wardrobes, offering a unique blend of comfort, style, and versatility. Whether you’re looking to create a laid-back athleisure outfit, add a touch of edge with vintage graphics, or elevate your casual ‘fit with premium heavyweight fabrics, there’s an oversized tee for every occasion.
The key to pulling off this trend lies in the details—getting the right fit, considering proportions, and balancing your outfit for a look that’s effortlessly stylish yet intentional. By pairing your oversized tees with complementary pieces and accessories, you can achieve a variety of looks that are as comfortable as they are fashionable.
There are so many ways for guys to style oversized t-shirts, so whether you’re lounging at home, heading to the gym, or stepping out to run errands, the oversized t-shirt is a reliable go-to for fresh fits and confidence-boosting style.
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There’s a handful of items that create the perfect capsule summer workout. The oversized T-shirt is one of them, and a men’s tank top is another. This closet classic is essential for gym ‘fits and casual wear, find yours in our guide to the best men’s tank tops and how you can style them.
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