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Cool Men’s Sweatshirts To Keep You Toasty In Style

The only way to stay warm whilst staying cool.

With the first week of winter in the rear-view mirror, the growing importance of layering is becoming obvious to most of us. We’ve already covered most of the key pieces – overcoats, lightweight jackets, and sports coats. The next big one is the right sweatshirt.

It’s hard to argue against the versatility of a sweatshirt. They’re perfect for loafing about on the couch when it’s pissing down outside, or combining them with tailoring to get you through that one day of the year when the office heating shits itself.

Today we’ve combined a list of top notch sweatshirts because it’s getting much colder outside than we’d like, and you deserve to look somewhat dashing while you contemplate the long-term consequences of hypothermia.

How Not To Look Like A Bum

Michael B. Jordan has the right idea

As ridiculously comfy as sweatshirts are, it’s easy to look like a bit of a slob if you aren’t careful. The first nugget of wisdom to keep you out of vagrant territory is to pair oversized pieces with more tailored items. Slim jeans with a sloppy joe sweater, for example, will illustrate to people that you haven’t been booted to living on the streets (yet). Tailored layers are another handy option.

A collared oxford shirt underneath a sweater, for example, can always do justice because a) layering in winter is a fundamental survival tool and b) it’ll smarten up your overall look. Finally, the last tool for avoiding the ‘bum chic’ is to look after your gear.

Sweaters can peel, warp, and decay if you don’t respect them. Fold sweaters in storage, rather than hanging them – this will stop the fabric warping and keep things looking crisp over time. Moths love chewing their way through sweaters, so try to ventilate your wardrobe, and brush your clothes regularly (moths can deposit eggs on clothes, sneaky fuckers).

Walking around in a sweater that has more holes in it than Donald Trump’s internal logic never looks good.


A Mr Porter exclusive, this is the kind of sweater you buy when you’ve already got a dozen luxury watches and a second yacht seems like a bit of overkill. In burnished orange and boldly patterned with Gucci’s signature motifs, Gucci have swung for the fences with characteristic elan, producing this in Italy with 100% loopback cotton. If there was anything you could wear that makes it impossible to fly under the radar, this is it.  Because this sweatshirt really doesn’t leave much to the imagination, pair it with muted staple colours and no other patterns. A pair of navy chinos and a pale blue shirt will do the trick. And remember that you could have a weekend in Bali instead of buying this, but remember that comparison is the thief of joy.

 BUY $2,355

Stella McCartney

The daughter of you-know-who, this sweater belongs to Stella McCartney’s first foray into luxury menswear, which draws on personal and cultural influences despite the enormous shadow of her old man’s legacy. This sweater is made with premium cashmere and wool, so it deserves a bit more respect than what you’d normally offer to your supremely-thrashed crewnecks at the bottom of your drawers. In an oversized cut with long dimensions, this bad boy suits an informal ensemble with distressed jeans, boots, and a fisherman’s beanie.

 BUY $815

Nike ACG

Always on the prowl for sartorial innovations, Nike have recently introduced the ‘All Conditions Gear’ collection, designed to carry you through anything from a reluctant hungover trek up a steep hill or just a normal day where an elevated heart rate is totally outside the realm of possibility. This black sweater combines durable Tech-Fleece materials with understated design, and has a few cool perks to sweeten the deal: it’s even got a compartment for your headphones, because no one should have to exercise with their mrs without a bit of aural encouragement coming their way. This should fit into the rest of your sportsluxe rotation, so pair it with cuffed sweatpants, white sneakers, and a beanie and you’ll be set.

 BUY $200

Thom Browne

Beyond his acclaimed suiting collections, Thom Browne has done the hard yards to keep guys warm in winter. This sweatshirt pairs understated grey with his distinctive triple stripe. It’s got the quintessential Thom Browne proportions – tailored and a touch shorter than usual – so it’s a perfect option for smartening up your winter wardrobe. This is made in Japan from first-class cotton, and would look just as good in the office with a shirt and tie as it would in its own for a low-key weekend aesthetic. It also comes in navy with contrasting white stripes – we won’t hold it against you if you can’t resist buying both.

 BUY $586

Neil Barrett

With substantial experience in luxury design, Neil Barrett’s personal venture into luxe menswear sees unconventional motifs marry the classic foundations of the male wardrobe. By no means for the conservative gent, this sweater confidently amalgamates designs that shouldn’t be mates – it’s likely you don’t often see Che Guevara and a Greco-Roman bust in the same room. This sweater is made from scuba fabric, so it offers good stretch and some resistance to the inclement conditions. It’s more fitted than a standard crewneck, so you can combine this with tailored layers for your corporate gig, or your athleisure kit for a lazy weekend off.

 BUY $549

Polo Ralph Lauren

It’d be unfair to exclude one of the princes of menswear from your trans-seasonal wardrobe wishlist. This white cotton sweatshirt evokes classic preppy style, without making you look like you’re heading off to watch a lacrosse match. It’s made from 100% pure cotton in a loopback weave, and in white it gives you the option to play around with colours elsewhere in your outfit. It’s a fitted cut, and they recommend taking a size larger than normal if you’ve been doing time in the weights room. Wear this with a pale blue oxford, indigo jeans, and chelsea boots, and you’ll be sorted for any daytime or evening contingency (except maybe playing lacrosse).

 BUY $122

Dolce & Gabbana

If you’ve already got your hands on the staple navy and grey crewnecks, you’re in an appropriate position to broaden your sartorial horizons and wear something that’ll frighten your parents. This sweatshirt poses a triple-threat pattern combination of zebra prints, florals, and stripes, making it a solid choice for the bold and brazen. It’s made in Italy from loopback cotton, so it’s super robust and will see you through more than a few winters. Because this sweatshirt is heavy on the details, you don’t need to go overboard elsewhere. Stick to the basics, in darker tones, and remember that this bad boy will set you back a few week’s rent (but it’s totally worth it). 

 BUY $642


Canadian fraternal design team DSquared2 are never afraid to take a classic and tweak it for their own sartorial amusement. This sweatshirt is a super alternative to a standard wool crewneck, adding contrasting stripes for a point of difference if you’ve found the ordinary staples less than inspiring. In a poly-cotton blend, take this one in your normal size and pair it with black jeans and white sneakers on a colder day, or navy shorts when it starts to warm up again.



Although normally linked to the development of the trench coat, Burberry are the furthest thing from a one trick pony. This cotton-blend sweatshirt is designed in deep navy, so you’ll never feel out of place in it and you’ll never such a fundamental staple go out of style. This is designed in a regular fit, so no stress if winter has got you adding a bit of size, but it’s not so loose that you couldn’t wear it over an open-collar shirt if you felt so inclined. Wear it under your Burberry trench coat with khaki chinos and desert boots for a dressed-down, winter appropriate substitute to your normal shirt-and-jeans Saturday night outfit.

 BUY $714

Mason Margiela

An oversized option for gents that like or need a bit of extra room, this Mason Margiela sweater is a good alternative to the run-of-the-mill crewnecks that crowd wardrobes and shopfloors. It’s 100% wool, which ensures it’s crease resistant and robust against prolonged wear. In khaki, it’ll go well with other staple colours and blend in with the basics you already own in abundance. This is best suited to your off-duty, no fuss days – wear it with your favourite distressed jeans and chunky boots and maybe your hangover will be a little bit easier.

 BUY $694


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