The Playbook For The Modern Man

Coolest Men’s Sweatshirts That Will Keep You Toasty In Style

It’s time to elevate your sweater game.

  • LAST UPDATEDMonday 13th January, 2020

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.


Acne Studio’s knit range is favoured for its understatement and versatility. Their sweaters are heavyweight all-rounders that can get the job done with jeans and sneakers or a dressier boot and chino combination. Acne probably suit a more cashed-up gent, but the sheer longevity of everything they do puts them at the top of our list for knits to try this winter. 


Sometimes it’s hard to ball out on a budget, but Uniqlo have got you covered. Most of their knits hover around fifty to a hundred bucks and their their range covers everything from cashmere to extrafine merino wool. 


Ateleir de Production et de Creation, mercifully shortened to APC, are known for their denim foremost but they’re no slouches when winter’s on the horizon. Their latest run of cotton sweaters go between simple navy and grey to stripes and pastels, so there’s something for the conserative and fussy shopper alike (just be prepared to drop a bit of coin in the process). 


AMI’s lofty origins on high street belies their focus on simple, wearable kit any guy can get around. AMI’s ribbed cotton sweaters are perfect for layering under jackets or going solo, and the lack of prints and trendy colourways should make it easy to integrate with your existing wardrobe. 

John Elliot 

John Elliot – understated, foundational, not too trendy – is a solid advocate for the more subdued side of menswear. Knit-wise, it’s all about good fits and easy colours that won’t turn heads. Off-duty simplicity is the name of the game here, so try their textured cotton pullovers with jeans and sneakers or under a jacket for winter. 

Maison Labiche 

If you’ve noticed a theme around understatement, it’s deliberate. Maison Labiche sweatshirts are focused on key colours – navy and grey – in a comfortable, roomy fit that’s suited to when you’re not on a mission to impress, but don’t fancy looking like a seedy wretch on Sunday morning. 

Maison Kitsune

With origins as a record label, Maison Kitsune’s latest run of sweaters add bold prints and colourways without veering into TMI-territory. The focus is still on natural materials like wool and cotton, and a versatile fit with universal appeal. Well worth the look if you’ve got plenty of staples already and are keen for a point of difference.

Stone Island

Stone Island had an infamous spot among football hooligan culture, but don’t hold that against them (besides, we’re not really sure anyone actually likes soccer). This season, they’ve got a range of plain crewneck pullovers in a bunch of colours that look the part next to jeans, chinos, or even sweatpants.


Sunspel are the closest thing to a classic statement of luxury Brit menswear without calling to mind polo, the peerage, or terrible weather. Their fine merino pullovers, worn under a suit or on their own, are for the understated guy who doesn’t need a heap of colour and pomp to get it done.


Household favourites, J. Crew always have their finger on the pulse but never stray too far from the year-in, year-out staples you can never have too much of. J Crew knitwear won’t offend sensibility or push boundaries, offering versatility that’s hard to beat.

James Perse

Angeleno James Perse might draw inspiration from the surf, but he’s not about to call you dude or throw a shaka in your direction. His simple (and ridiculously well-made) jersey pullovers are perfect on their own in autumn or as part of a layered look in winter. James Perse will attract the well-heeled gent – his sweatshirts will set ya back almost 250 bucks. The good thing is you only need to to buy one.

Holiday Boileau

Originally a travel magazine, Holiday Boileau took a short break (some 37 years) before an ambitious relaunch as a mens clothier, and we’re not mad they moved off from advertising the Greek Islands. Their seasonal knits combine refreshing colour and the odd print here and there that reminds us of their adventurous heritage. 


A menswear stalwart since ’69, Aspesi’s loopback cotton jerseys bring together smart understatement and strong production values. Wear them with smart indigo jeans, a white shirt, and chelsea boots for the right kind of Saturday night look. 


Canadian duo DSquared2 are not for the faint of heart or shy of print. Never afraid of a pattern here or a cheeky motif there, Dsquared are for the outgoing gent for whom understatement is another word for boring-as-shit. This season, they’ve put a foot in either column with some simple knits and their usual printed fare, so check them out to plug those gaps in your wardrobe. 

Save Khaki United 

Save Khaki United might sound like a student interest group but fortunately, they’re not quite so insufferable and actually make killer knitwear. Save Khaki’s formidable range of sweats are all about comfort and simplicity: classic colours, a tailored fit, and good craftsmanship. If you need to pad the wardrobe with the foundations, this is the brand to see. 

Nike ACG

There’s nothing Nike can’t reach – whether it’s apparel for elite sportsmen or the next big thing for sneakerheads. Nike ACG sits somewhere between the brands athletic roots and streetwear, offering oversized printed knits that you could wear with kicks (maybe adidas this time) and tailored sweatpants for a simple off duty look. 


Mixing jungle patterns and oversized cuts, Kenzo are a slightly different take on the weekend sweater. We’re on board with their latest run of Tiger printed sweaters, giving you a point of difference without veering into obscene and obscure territory. Pair them with indigo denim and white sneakers for an easy weekend look. 

Reigning Champ

Canadian outfit Reigning Champ deserve their name as the leaders of off-duty athleisure threads. Reigning Champ remind us of an upscale AS Colour: simple, durable basics you can wear season after season. The quality’s all there and their clean, understated colourways can slot into any outfit you pull from the wardrobe.

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