The oversized T-shirt trend is a comfortable and stylish look that has been embraced by men of all ages. These relaxed, roomy tops offer a laid-back vibe that’s perfect for casual days. But figuring out how to style an Oversized T Shirts in a way that looks intentional, not sloppy, can be tricky. That’s why we’re breaking down the best ways for guys to rock an oversized T-shirt from day to night. Get ready to upgrade your casual fashion game!

Oversized t shirts + Chino Shorts

Pair an oversized t-shirt with some casual chino shorts for an easy, breezy weekend look. This combo is perfect for running errands, grabbing lunch, or kicking back.

When choosing shorts, go for a longer, slightly roomier fit that hits around the knee or above. This helps balance out the drapey volume of the oversized t-shirts. Chino shorts in classic khaki, olive green, or navy are versatile options that can be dressed up or down.

On top, solid-coloured oversized T-shirts in neutrals like white, gray, or black provide a clean base. Or get playful with a graphic tee or bold print. Roll up the sleeves to keep things casual yet neat.

Finish off the look with some low-top sneakers or slip-on canvas shoes. For extra laidback flair, you can accessorize with a baseball cap and sunglasses. It’s the perfect stylish yet comfy outfit for weekend warrioring around town.

Oversized t shirts + Skinny Jeans

Embrace a more contemporary, minimalist style by pairing an oversized t-shirt with fitted skinny or slim jeans. This look gives off major cool guy vibes.

The key here is creating an interesting contrast between the slouchy, oversized fit on top and the sleek, tapered fit on the bottom. Go for a plain oversized tee in black, white, gray, or even an earth tone like olive or tan. Avoid graphics or logos to keep things clean and minimal.

Next, slip into skinny or slim jeans in a dark wash like black or indigo. These help streamline and elongate your frame while letting the t-shirt be the focus. For an extra laid-back touch, consider rolling or cuffing the hems of the jeans.

Lastly, finish the outfit with some fresh white sneakers and minimal accessories like a watch or a simple necklace. You’ll have an easy, stylish outfit that looks thoughtfully put together.

Oversized t shirts + Chino Pants

For a more polished, modern take on oversized T shirts, style them with tailored chino pants. This combo is perfect for casual workdays, weekend brunches, or running errands around town.

Regarding chinos, stick to a slim or skinny fit in classic colors like khaki, olive green, or navy. The tailored cut of the pants helps offset the relaxed vibe of the oversized top.

On top, oversized T shirts with a simple pattern like stripes or color-blocking look crisp yet casual. A solid-coloured tee in a refined hue like burgundy, hunter green, or camel also works nicely.

Pull the whole look together with sharp leather sneakers or loafers and a canvas belt with a sleek buckle. If desired, accessorize minimally with a timeless watch and sunglasses. The result is a contemporary ensemble that looks stylish and put-together without being too stuffy.

Oversized t shirts + Black Jeans

With some clever styling, you can easily make an oversized T shirt work for casual evening plans like date night or dinner with friends. The formula is simple—just swap in some slim black jeans.

The key to nailing nighttime style is choosing oversized t shirts made of luxe, drapey fabrics like silk, viscose, or modal blends. These elevated materials instantly elevate the whole look. Stick to moody, solid colors or tonal prints with a sophisticated touch.

Pair the tee with slim or skinny black jeans for a sleek, streamlined silhouette. The dark denim works well for the evening while still keeping things laid back. Finish it off with some fresh white sneakers or chelsea boots.

Layer an overshirt, bomber jacket, or lightweight blazer over the look to add extra polish. Accessories like a simple necklace, a leather strap watch, and a tote or crossbody bag can further dress things up.

Voila – you’ve got a stylish night-out outfit that’s cool, comfortable and looks intentional.

Oversized t shirts + Joggers

To channel some major athleisure vibes, wear an oversized T shirt with tapered joggers or sweatpants. This sporty streetwear look is perfect for casual weekend hangs, errand runs, or weekly workouts.

For the tee, embrace the athletic aesthetic with an oversized style in a breathable fabric like cotton or moisture-wicking blends. Graphic tees or bold-coloured paneling or patterns add extra visual interest.

On the bottom, some slim, ankle-length joggers or sweatpants in black, gray, or even camo prints continue the sporty vibe. Ensure they have a tapered shape so they don’t look too sloppy or baggy when paired with the oversized top.

Lace-up some fresh white sneakers or cool kicks like Air Force 1s or Jordans. Add a baseball cap, crossbody bag, and mirrored sunglasses to embrace the streetwear-inspired look fully.

Oversized t shirts + Drawstring Shorts

For a super laid back, relaxed outfit perfect for lazy days, vacations, or cottage weekends, pair an oversized t shirt with some drawstring shorts. It’s the ideal comfy yet cool uniform.

Choose a casual, knee-length style in breathable fabrics like linen blends, cotton, or jersey when it comes to the shorts. Opt for patterns like plaids, stripes, or prints for extra visual interest and texture.

On top, the oversized t shirts should be the no-frills, well-worn version you’ve had for years. Think of super soft fabrics and vintage band/graphic tees to amplify casual cabin culture. Raw or distressed hems and necklines add to the lived-in feel.

Finish the outfit with rugged slip-on shoes, sandals, or boat shoes, perfect for shore days or lake trips. Accessorize with a baseball cap, sunnies, and a bracelet for that ultimate laid-back vacation vibe.

The Modern Minimalist: Oversized t shirts + Skinny Jeans Embrace a more contemporary, minimalist style by pairing an oversized t shirt with some fitted skinny or slim jeans. This look gives off major cool guy vibes.

The key here is creating an interesting contrast between the slouchy, oversized fit on top and the sleek, tapered fit on the bottom. Go for plain oversized T shirts in black, white, gray, or even an earth tone like olive or tan. Avoid graphics or logos to keep things clean and minimal.

Next, slip into some skinny or slim jeans in a dark wash like black or indigo. These help streamline and elongate your frame while letting the t-shirt be the focus. For an extra laid-back touch, consider rolling or cuffing the hems of the jeans.

Lastly, finish the outfit with fresh white sneakers and minimal accessories like a watch or a simple necklace. You’ll have an easy, stylish outfit that looks thoughtfully put together.

No matter your personal style, an oversized T shirt outfit is perfectly suited for you. The key is finding the right balance of proportions through tailored bottoms or layers. With a few simple styling tricks like front tucking or accessorizing, you can transform a basic oversized tee into a fashionable-forward, relaxed and comfortable look. So get ready to make the most of this trend!