Top 6 Oversized Men’s Clothing Trends for 2026

The popularity of fit is a massive pendulum, perpetually swinging from loose to slim and back again over the course of decades. As one becomes the default setting among the mainstream, the trendsetters and tastemakers at the forefront of fashion begin to go in the opposite direction. Gradually, the masses catch on, and the process begins again.

Right now, we’re at one of those turning points. Baggy jeans and boxy outerwear have become ubiquitous, and the more adventurous dressers out there are already beginning to look back to the ultra-fitted, figure-hugging cuts of the noughties for inspiration rather than to poke fun at.

For most of us, the best course of action is to remain neutral. Aim in between and, in theory, you’ll always find yourself on the right side of history. But there are pieces on both sides that you can incorporate without leaning too far in either direction.

Below are the oversized pieces we still believe are worth having in your wardrobe.

Relaxed-Fit Denim

The characteristic thickness and weight of denim can make it feel constricting if the fit isn’t forgiving. Relaxed-fit denim takes an easygoing approach, allowing the legs to move more freely without inhibiting movement.

Think less baggy and more loose; the goal is for the fabric to drape naturally around the legs rather than gather awkwardly on top of your shoes. Keep proportions balanced elsewhere by steering clear of anything too fitted and enjoy the ease of movement.

Slouchy Overcoat

We’re big fans of a bit of throw-it-over-anything outerwear, and it doesn’t get much better than a slouchy overcoat. With a roomy cut and relaxed raglan sleeves, this type of coat feels far less stiff and stuffy than a traditional tailored topcoat, without losing its formality.

It’s still smart enough to drape over a well-cut suit, but it won’t look out of place paired with jeans and a hoodie either. In a textured wool fabric, perhaps with a subtle check pattern running through, it’s a piece of outerwear that will pay for itself over many decades of wear.

Loose Worker Overshirt

Good workwear should be comfortable and promote a full range of motion. That’s why the best blue-collar overshirts are cut nice and loose through the body.

Not only is this practical, but it’s also great for layering, enabling you to stack a base layer and some knitwear underneath so that you can wear it either as an outer layer or under something more substantial.

Go for heavyweight cotton fabric, like twill or duck canvas, and wear it to death.

Wide-Leg Pleated Pants

The most interesting outfits often play with proportion, creating either contrast or continuity between top and bottom. A pair of pleated pants widens the lower half, creating an interesting silhouette and elevating the less showy garments within an outfit.

Go for classic chino material in beige or olive to keep things casual, or dress it up with worsted wool for a more tailored look.

Relaxed Suit

If you grew up in the skinny suit era, you could be forgiven for thinking that tailoring is uncomfortable by default, but it doesn’t have to be. Going in the opposite direction and favouring floaty over fitted makes everything feel more relaxed.

Suddenly, a suit is something you look forward to wearing rather than dread, feeling awkward and uncomfortable in.

Just make sure it sits well at the shoulders, fits properly at the waist and the hems fall where they’re supposed to, and you should be good. If in doubt, ask a tailor.

Oversized Tee

The simplest of all the oversized garments, a loose-fitting tee is easy to wear and hard to get wrong.

It instantly brings a bit of streetwear swagger to the table and has the added benefit of keeping you cool and sweat-patch-free in hot weather, thanks to increased airflow.

But it’s not just for summer – during the colder months, it’s an excellent tool for layering, letting you create stacked looks by pairing shorter pieces like cropped knits and boxy jackets.

Oversized Hoodie

A hoodie should be one of the most inviting and comforting pieces in your wardrobe. Something you instantly feel cosy and comfortable in.

One of the best ways to ensure this is to go slightly oversized with it. We’d suggest going for one with raglan sleeves and a boxy cut, but with nice, tight ribbing around the hem and cuffs to keep you from getting too lost in it.

Choosing a heavyweight cotton version can help give it a bit of structure, too.

Boxy Puffer Jacket

The puffer jacket has always leaned oversized by nature, but the boxier cuts feel especially relevant right now. Shorter in length and wider through the body, this shape avoids the sausage-casing effect of overly slim padded jackets and instead creates a clean, architectural silhouette.

The key to getting the look right is restraint. Keep colours muted and detailing minimal so the volume does the talking without tipping into ski-slope territory.

Worn with straight-leg jeans or relaxed tailoring, it delivers warmth, practicality and a quietly confident sense of proportion.