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The Brands Making The Coolest Oversized Sweatshirts For Men

Whatever you're into, get comfortable with an oversized sweat. These are the labels producing the best versions for 2024, from streetwear independents to high-end designers.

Words by: Charlie Thomas

There’s nothing more comfortable than an oversized sweatshirt. That’s right, we’re calling it. Don’t write in. If you want something to relax in on weekends, lounge around the house in or to travel in both style and comfort, this is the piece for you.

With a rich heritage in American sportswear – it was created in the first half of the 20th century as a warm-up top for American football players – the sweatshirt has come a long way in the decades that followed. Adopted by style icons ranging from Steve McQueen to Muhammad Ali, it’s now a wardrobe staple, as much loved for its classic look as its incredible comfort.

Go oversized though and its benefits are only bolstered. Even more comfortable and with a distinct streetwear-inspired aesthetic, the oversized sweatshirt is an underrated option for fall and winter layering, whether you plan to wear it with matching sweatpants or go smarter with chinos or tailored trousers.

The best brands for oversized sweatshirts include up-and-coming independents, global powerhouses and quiet luxury specialists. Whatever you’re into, get comfortable with an oversized sweat.

The best brands for oversized sweatshirts

Organic Standard

Organic Standard’s sweats are difficult to top with their heavyweight organic cotton fabrics, wide-ranging color palette and exceptional fits.

The brand’s oversized sweatshirts are particularly good with their dropped shoulders, roomy cuts and relaxed, comfortable hand-feel.


The all-American workwear brand has been producing durable, well-made wardrobe staples for decades. Its sweatshirts have long been a part of its collections, and typically come in soft yet hardy fabrics and relaxed fits.

Wax London

If you’re on the lookout for menswear basics, Wax London should be near the top of your list. From simple tees through to overshirts and even suits, the British independent has you covered.

For its oversized sweatshirt, it’s gone with a 100% organic cotton fabric and given it a loopback finish on the reverse for plenty of breathability and softness against the skin.

You’ll also find dropped shoulders, an embroidered ‘W’ on the cuff and twin-stitch detailing for added durability.


Pangaia specializes in well-crafted and green-minded sportswear, so you can expect its oversized sweatshirts to be of the finest quality.

Well-sourced cotton jersey meets relaxed fits and subtle detailing, including Pangaia’s signature script branding, which further separates them from the pack.


Levi’s has long been known as the destination for denim since it started producing jeans in the American West at the turn of the 20th century.

Today the brand is just as renowned for its casualwear though. For its oversized sweatshirts it makes use of easy-to-wear hues like navy and grey, as well as soft cotton fabrics that only get better with age.


Champion was one of the very first companies to make sweatshirts in the first half of the 20th century, so it’s fair to say the US brand knows a thing or two about them.

Crafted from high-quality cotton jersey and with its signature embroidered ‘C’ applied to the arm or chest, Champion’s oversized sweatshirts are about as good as it gets.


Vans doesn’t tend to reinvent the wheel with its sweatshirts. True to the California brand’s laid-back design ethos, its oversized sweats come with minimal branding, comfortable, relaxed fits and durable fabrics.

Try them with a pair of wide-legged cargo pants and finish with some classic Authentics.

Carhartt WIP

Detroit-based Carhartt has been producing classic workwear for well over a century, so if you’re looking for hard-wearing, durable sweatshirts, this is the place for you.

The brand also designs more contemporary pieces under its Work-in-Progress sub-label, which is where you’ll typically find its oversized pieces.


Adidas has recently been stepping up its sustainability credentials, so chances are you’ll be able to find one of its oversized sweatshirts made from at least partially recycled materials.

Its All SZN range is particularly worth seeking out, with the sweats typically crafted from fleece-back cotton and incorporating subtle branding as well as the classic triangle stitch at the neckline.

Admiral Sporting Goods

Admiral Sporting Goods’ classic pieces are heavily inspired by vintage designs, with the brand’s sweatshirts adopting a throwback fit that includes dropped shoulders, a boxy waist and relaxed hem.

Available in a range of vibrant and muted shades, this is the kind of sweatshirt you can dress up with tailored chinos and commando-soled boat shoes for a contemporary preppy aesthetic.


P&Co doesn’t produce a huge variety of styles. What it does do is hone in on a handful of classic staples and refines them to perfection. Take the brand’s sweatshirt, for instance. It’s crafted from a heavyweight 440gsm brushed French loopback cotton, making it incredibly soft against the skin and ideal for tackling the cooler months.

Taking inspiration from vintage gym kit, it’s cut with a boxy middle, dropped shoulders and features a V-stitched neckline and back yoke for an added artisanal touch.


When it comes to fit and finish, COS isn’t shy of pushing the envelope. Known for its pared-back, minimal designs, the brand is always good for a sweatshirt or two, whether in a regular fit or something more directional.

For the latter, check out its 100% organic cotton jersey options, with their laid-back, boxy fits, ribbed hems and overlocked stitching.

Dries Van Noten

Dries Van Noten is renowned for its expressive use of print, pattern and color, and dramatic proportions in everything from tailoring to sportswear.

The label’s oversized sweatshirts definitely carry that DNA: stocky fits, muted colors and memorable prints are all present and correct, and they’ll work with casual and tailored trousers, too.

Acne Studios

Trendsetting Swedish label Acne Studios has become increasingly bold and colorful in recent years. Its oversized sweatshirts are a good example of the direction: out with Scandi minimalism, in with huge logos, acid colorways and even big, glow-in-the-dark prints.

Of course, the brand hasn’t completely abandoned the stripped-back aesthetic. If all you need is a luxury-grade jersey sweatshirt in plain black, you won’t find many better than Acne’s.


It started as a yoga apparel brand, but Lululemon was well-placed to take advantage of athleisure boom. Even before the COVID-19 pandemic, people had collectively decided that we could wear slouchy, comfortable sportswear all day every day, even to work – and Lululemon is a natural choice.

The label’s oversized sweats come in a fleece back fabric and muted, considered palette. Ideal for travel and lazy weekends as well as laid-back 9-5s.


A British take on luxury streetwear, Represent does classics like bold printed tees and embroidered varsity jackets, plus an extensive collection of sweatshirts. Its oversized options fit boxy with dropped shoulders and a wide hem.

As streetwear sweatshirts go, the collection is quite muted – no huge graphics or illustrations, just some good-looking front-and-back logos and slogans. All the better for pairing with a wider selection of your wardrobe.


Arket is the H&M group’s grown-up brand for simple, considered basics and its collection of sweatshirts typifies the label’s approach. Laid-back, wearable, block-colour designs will go with anything, and they’re also made to last.

Arket’s relaxed sweatshirt is made from recycled, heavyweight cotton terry. That makes it warm and comfortable and lends itself to interesting, blocky silhouettes, too.

Cole Buxton

Like Represent, Cole Buxton is another British streetwear label, offering a luxe take on classic sportswear. Prints, patterns and logos are kept to a minimum, and while you’ll find a few sweats in bright pink or cobalt blue, much of the collection is rendered in black and white.

The fit is old-school and boxy, with dropped shoulders and wide hems. Some models are even cropped, exaggerating the blocky cut even further.


Relaxed-fit sweatshirts are a big part of the uniform at Weekday, the H&M group’s more casual, slightly streetwear-leaning sub-brand. Its collection includes midweight and heavyweight sweats, some in block colors, others with prints, logos or distressed detailing.

There are also a few that play with different fabrics, as fleece lines up alongside the more common cotton jersey. And they’re comfortably the most affordable options on our list.

Why go oversized

Man wearing oversized brown Carhartt WIP sweatshirt with white T-shirt and baggy raw denim jeans

Carhartt WIP

Similar to whether you opt for an oversized hoodie or one with a regular fit, one of the key benefits of an oversized sweatshirt is the comfort factor. Regular-fitting sweatshirts are already known for their comfort, with their soft cotton jersey fabrics, fairly close fits and relatively breathable, lightweight construction.

But oversized sweatshirts turn everything up to eleven. The excess fabric of an oversized fit gives them an almost blanket-like feel, allowing the wearer plenty of room to move without any pulling across the chest or stretching of the sleeves. As far as loungewear goes, there is nothing more comfortable than an oversized sweatshirt.

Plus they’re just as versatile as their regular fitting alternatives. You can wear oversized sweatshirts with everything from jogging bottoms and shorts to smarter pairs of chinos, denim jeans or even tailored pants if you’re so inclined.

The other reason you might want to consider an oversized sweatshirt is the look they offer. Oversized sweatshirts reference classic skatewear in their bagginess, which has been favored by the sub-culture for decades for its comfort and ease of movement. More relaxed fits also hint at a wider streetwear-inspired look, so if that’s the look you’re after, bring an oversized sweatshirt into your rotation.

As a starter, try combining an oversized sweatshirt with a pair of relaxed-fitting cargo trousers, and finish with some Vans or Converse for a 90s-inspired weekend look.

Things to consider before buying


Two oversized Represent sweatshirts in dark grey and white laid out on concrete floor


If you want a classic sweatshirt, the kind with roots in early mid-century sportswear, there’s only one fabric to consider. Cotton jersey has long been the choice for sweats, beloved for its lightweight, breathable weave and incredibly soft handle. Originally rendered in light grey marl, you can now find cotton jersey in any and every shade, from bright right through to deep green.

There are a couple of variations to be aware of though, which come down to the finish on the fabric’s reverse side. The most traditional form of cotton jersey used for sweatshirts has a ‘loopback’ finish, which has lots of tiny little loops of fabric on the underside. These were designed back in the day to draw moisture from the body, keeping the wearer dryer for longer. Modern performance fabrics have since rendered this jersey redundant for exercising in, but the fabric remains exceptionally comfortable and kind to the skin.

The other option you’ll come across is cotton jersey with a ‘fleece back’ reverse. This is when the cotton is brushed, giving it a fleece-like, almost cotton wool finish. This fabric is typically slightly heavier and warmer than loopback cotton and is best worn in the colder months.


Man wearing Wax London black oversized sweatshirt with dark raw denim jeans

Wax London

Given its associations with streetwear, oversized sweatshirts often come in a multitude of colors and patterns, with logos and prints featuring prominently. While you could go monochrome with a grey, black or navy oversized sweatshirt, there are plenty more vibrant options out there.

This is a garment that’s ideal for use as a statement piece, whether in the form of a brand logo on the chest, an all-over pattern or just a solid block color, which can break up an otherwise monochrome fit. Try, for example, wearing a logo sweatshirt over a pair of pleated trousers and some minimal white sneakers for an easy, laid-back evening look.


Three oversized sweatshirts by Cole Buxton in green, charcoal and grey laid out on concrete floor

Cole Buxton

The overall look and feel of a sweatshirt can drastically change with the details. For a timeless, vintage-inspired design, there are a few things to look for. There’s the triangle stitching at the neckline, which was said to be originally designed to draw sweat down away from your chest, but today is just an aesthetic feature.

Classic sweatshirts also often had subtly contrasting stitching throughout – white thread on a grey marl fabric, for example. If you’re a fan of the old-school aesthetic, look for raglan shoulders, which have an unbroken panel of fabric from the neckline down the shoulder and sleeves, as opposed to a set-in sleeve, which has a hem at the shoulder.

For a more contemporary feel you can of course ignore these small details by losing the contrast stitching for a more minimal look. Whichever style you go for, an oversized sweatshirt is bound to add a relaxed, comfortable feel to any casual fit.

How an oversized sweatshirt should fit

Man wearing oversized grey Represent sweatshirt over long white T-shirt with black pants and a crossbody bag


There are no strict rules to how an oversized sweatshirt should fit, and how baggy you go is largely down to you. If you’re unsure, it’s best to avoid going too balloon-like. And, as with oversized hoodies, try to seek out a piece that’s been designed to be oversized rather than just buying a regular-fitting garment and sizing up.

A sweatshirt that’s been designed with an oversized fit will usually have a baggier chest and waist and a more relaxed hemline that won’t cling to your body. The shoulders will also be dropped, hanging a couple of inches over the end of your own shoulders, while the arms will have more room. The sleeves shouldn’t end too far beyond your wrists though, and the hem length should only be an inch or so longer than a regular-fitting sweatshirt.

This way it looks like it still ‘fits’ you, rather than being overly big and shapeless. As always, it’s best to try a few on in person if you can, as this is really the only way to assess whether you’re happy with how it looks and drapes on your body.