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January 01, 2020 5 min read

How to Rock an Oversized Long-Sleeve Shirt?

You might remember baggy clothes as a wardrobe staple back when you were in grade school. As the fad faded, clothing became a bit more fitted. In recent years, slim-cut shirts, skinny jeans, and other tailored pieces have been at the forefront of men’s fashion. But as trends tend to go, menswear is beginning to swing back in the other direction.

Believe it or not, loose-fitting apparel is back. That being said, it’s a lot different this time around. Oversized clothes are more boxy than baggy and more intentional than sloppy. One of the edgiest looks right now for both men and women is the oversized shirt.

Are you wondering how to style an oversized shirt? If so, Affliction Clothing has your back. Our threads are all about making statements with a bold assertion. Here’s what you need to know about this updated take on loose clothing, including how to nail an oversized shirt outfit.

Oversized Tees vs. Oversized Button-Downs

The oversized trend includes a couple of types of shirts: oversized tees and oversized button-downs.

Oversized tees come in both short- and long-sleeve variations. They have a boxy cut and notably broad shoulders with sleeve stitching that usually starts a few inches down the arm. Short-sleeved t-shirts will have somewhat long and wide sleeves, sometimes reaching the elbow. Oversized full sleeve t-shirts for men will have the same square-shaped fit around the torso with wide sleeves that go all the way down.

These oversized edgy long sleeve shirts follow the same basic design as tees. However, they have traditional folded collars and buttons down the front. Most will also have a button at the bottom opening of each sleeve.

Oversized tees aren’t typically worn with oversized button-down shirts. So, if you love the look of a slouchy button-down, we suggest wearing it over a regular-fit t-shirt. Rock it unbuttoned or buttoned up to the top. For a look that’s a little more casual, roll up the sleeves of your button-down shirt.

How to Style an Oversized Shirt Outfit?

For most of the last decade, men’s fashion has embraced fitted cuts. We’re talking muscle tees, slim-fit button-downs, and pants much tighter than previously seen on men. While there’s definitely something to be said about slimming clothes that flatter your frame, boxy fits can look just as good, especially for an edgier look. Not only that, but an oversized shirt is all about being comfortable. Tight clothing conforms to the muscles and curves of a body, which can make some people feel self-conscious and restricted. Conversely, the square-shaped fit is all about presenting a bold and unexpected style.

No matter what style of shirt you wear, fit is extremely important. And yet, the right size fit for an oversized tee is entirely different than for other types of shirts. The key is finding the proper cut and wearing it with the right outfit. Keep the following tips in mind when styling an oversized shirt outfit.

Big, Not Baggy

An oversized shirt isn’t just a regular shirt in an extra-extra-large size –– it will have a distinct cut. Generally, this style of shirt will be wider around the torso with boxy sleeves. Some will be slightly longer in the back. Whereas baggy clothes are strictly casual, oversized pieces are suitable for all occasions. That is, as long as you get the right cut.

When you shop for oversized tees and button-downs, look for words like “boxy cut,” “relaxed fit,” or “oversized” in the description instead of just opting for the largest size. Most importantly, make sure you buy the shirt size you normally wear. With oversized clothing, standard sizes are simply larger with alternative cuts, so don’t go up a shirt size! Otherwise, you’ll end up with a shirt that looks baggy or a slim-fit tee that’s way too long and narrow –– neither of which is the vibe you’re going for.

Go for Slimmer Pants

Another crucial thing to remember about an oversized shirt outfit is that an extra-wide square-fitting top doesn’t call for loose-fitting pants. An oversized shirt with baggy jeans or other slouchy pants will also negate your intended look. Wide, relaxed-fit shirts should be paired with slimmer pants. 

Whether you opt for black denim, dark-wash dungarees, ripped jeans, trousers, or tailored chinos, keep in mind that the goal of an oversized shirt outfit is to look deliberate yet laid-back. For women, skinny jeans, leggings, or yoga pants pair well with oversized tops. During the warmer season, shorts are a great option for both men and women. Instead of looking like you rolled out of bed and threw on whatever clothes you saw first, your outfit should look curated.

No-Wrinkle Zone

A couple of decades ago, baggy clothes presented a careless, just-rolled-out-of-bed look. Today’s oversized apparel is totally different. While the cuts don’t hug the body, an oversized shirt will still feature specific tailoring. This trend includes pieces that are lax yet pressed –– and this means no wrinkles.

Choose Your Kicks

Luckily for you, oversized shirts go with most shoes. That said, our favorites for this look include oxfords, wing-tip lace-up boots, boat shoes, and Chelsea boots. Athletic shoes or simple sneakers in neutral colors are also excellent choices. Flat-soled trainers, lace-up sneakers, running shoes, and even basketball shoes will work. If you’re going for an edgier vibe, consider leather combat boots. For women, taller boots also look flattering with boxy shirts.

Lean Toward Athleisure

The easy-going aura of oversized shirts lend to a sense of leisure, and stylized basic boxy tees have an athletic feel. Why not put the two together and lean toward an athleisure theme with your outfit?

For this look, we recommend wearing slim-fit joggers or other athletic pants with an oversized shirt. Finish the ensemble with a pair of fresh trainers or sneakers. It’s all about pieces that are bold yet carefully selected. 

Tie It Together with Outerwear and Accessories

The right outerwear will tie the look together. Similar to pants, wearing a boxy top doesn’t mean you should wear extra-large sizes for the rest of your clothes. Finish your oversized shirt outfit with a jacket in the size you normally wear. Virtually any badass jackets will work, so rock your favorite denim jacket, leather coat, bomber jacket, or windbreaker.

Lastly, you can make this ensemble truly yours with a couple of statement accessories. Beanies and billed hats both offer a chill look. Bandanas and sunglasses can also add some unique character. 

An oversized shirt outfit can be dressed up or down and worn anywhere. Once you get the hang of wearing a boxy shirt, you’ll realize just how versatile and edgy this look can be.

Oversized Shirts and Other Statement Pieces from Affliction Clothing

At Affliction, we make boundary-breaking apparel for men and cool women's clothing that challenges the status quo. While we push the limits of alternative fashion, we also create flattering pieces in on-trend cuts and styles. We carry a wide range of long-sleeve, short-sleeve, and button-down shirts in relaxed fits. When you browse our inventory, you’ll also find outerwear, accessories, jeans, and warm-weather apparel. For bolder looks, you can even browse our unique prints. For something that really showcases personality, opt for a tattoo print long sleeve shirt or graphic t-shirt.

Our unique clothing is inspired by art and designed with innovation. And with a passion for comfort and a dedication to grit, Affliction Clothing embraces a laid-back lifestyle that’s also full of risks.

Take the risk of this reincarnated trend and start shopping for an oversized shirt outfit to curate your edgy look today.


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