How To Style The Oversized Trend For Men

Last updated: August 29, 2021

In the last years, the oversized trend grows more and more, from casualwear to tailoring. If you wondering how to pull off the oversized look, keep scrolling to find out.

Choosing The Right Oversized-Tee


It’s important to distinguish the intentionally designed oversized tee from your normal slim tee, three sizes bigger.

The t-shirt has to be looser than usual around your torso and sleeves. As for the standard length, prefer anything from hip level to the bottom of your crotch or slightly below.

You can either tuck into your pants or leave it as it is. However, the first choice shows an intention of a relaxed aesthetic, that you’ve thought well your outfit.

Regarding the sleeve length, the oversized tee has to be lower than your standard mid-bicep to elbow level.

Wide Top/ Slim Bottom

The contrast between the oversized t-shirt and the bottom half makes them look seem intentional.

Add a shorter denim jacket to have the t-shirt be longer than the jacket or a big, long coat to further accentuate the oversized look.

This outfit has a rock, grunge vibe to it, make it perfect for a concert or just a drink.

Slouchy Look

It’s fairly easy to start with but hard to master.

Grab a pair of your relaxed jogger pants or jeans and wear your oversized tee untucked.

Add jewelry like subtle chain necklaces, rings, or a nice watch to elevate the outfit and turn it from slouchy unkept to slouchy chic.

Hourglass Look

This outfit emphasizes both your upper body and your lower half as well.

Opt for straight-leg or wide-fit pants, high-waisted to elongate your body. Tuck your relaxed feel t-shirt into the pants and cinch in your waist to create that dichotomy between the two parts.

Or pair them with a regular fitting turtleneck to create the perfect balance.

The key is to not have a big taper on your pants, which would change the silhouette.

Opt for chunky shoes to add some weight to the bottom half of the outfit and really emphasizes that hourglass silhouette.

As for outerwear, go for a shorter jacket on top, create balance.

Structured Oversized

Prefer a pair of smart trousers with a pressed crease, tapered from the knee down, styled with an oversized sweater on top and minimal classic sneakers.

Adding a long coat on top will help you maintain some type of shape and structure.

The intention here is to create an oversized look from head to toe, that still has a strong structure to it.

Opt for a cropped hem on trousers, as it helps in creating that delineation between the pants and the shoes.