30 Stylish Winter Outfits For Men: How To Dress For Winter 2023
The colder weather allows us to get really creative with our looks. Here's how to dress in a practical yet stylish way for winter, including a wealth of stylish outfits that all men can pull off.
Ah, our good friend winter. Cold mornings, dark afternoons, the constant threat of rain and clouds. It’s not exactly enjoyable, is it? But there’s one saving grace for this harshest of seasons: the style.
For one, sub-zero temperatures allow for plenty of layering, which ensures more interesting and creative outfits. But for us, it’s all about the fabrics. Dense wools, lush corduroys, soft flannels and hardwearing moleskin are just some of the options available. Although designed primarily to keep us warm, they have the added benefit of feeling great against the skin, injecting an instant dose of hygge that’s sorely missing throughout the spring and summer months.
So, how can we make the most of this opportunity to flex our sartorial muscles? Whether you want to weather-proof your office wear or mix up your winter weekend attire, here’s how to nail cold-weather dressing.
How to dress for winter
As previously mentioned, if there’s one good thing about dressing in winter, it’s the chance to dig out some serious fabrics. Summer is all about lightweight, breathable fibres like linen and cotton. Winter requires thicker, denser materials – think chunky wools, heavyweight denim, sturdy twills and heritage cloths like herringbone and tweed.
This is something to celebrate. The colder months allow for plenty of experimentation as you can combine different textures to create really interesting, highly personal outfits. Summer is limited in this regard, with single layers taking priority because of the stifling heat. Winter, on the other hand, allows you to combine multiple garments – cotton jersey hoodies under textured wool overcoats, flannel overshirts under nylon puffer jackets, or ribbed knitwear under technical parkas, for example.
The options are limitless and should be fully embraced.
Don’t be too dull
Yes, the days are short and the nights are long, but that doesn’t mean your outfits have to reflect the dark and dreary climate. The warmer months might be the obvious time to break out the pastels and primary shades, but winter has its colour perks too.
Rich autumnal hues likes burgundy, racing green and burnt orange come alive in the cold and feel seasonally appropriate. It’s also a palette that mixes wonderfully with brown tones, ranging from chocolate and nutmeg to chestnut and copper, as well as earthy neutrals like ecru, stone and off-white.
Of course, tonal navy looks and all-black fits will always be a winter winner, but you shouldn’t be afraid to inject some life into your cold-weather attire. More often than not, the easiest way to do this is with a splash of colour.
Say no to soggy soles
Your choice of footwear is arguably the most important consideration when dressing for winter. There’s no point in splashing out on a fancy new winter coat and upgrading your knitwear collection if your shoes can’t cope with a downpour or icy surfaces.
The best winter-ready shoes and boots represent the pinnacle of shoemaking. They’ll usually be handmade using traditional processes and include robust leather uppers, chunky rubber soles and sturdy, water-resistant storm welts – ensuring you’ll stay comfortable and dry no matter the weather (trench foot is never a good look).
You can of course keep sneakers in your rotation, but for harsh, wet weather, a pair of durable Derby or Chelsea boots will always be a worthwhile investment.
When push comes to shove, winter dressing is all about keeping warm. This is where accessories come into play. A good quality scarf will help immeasurably, reducing windchill on your neck and face, but don’t just settle for the first one you see.
Search for a design in a solid, versatile colour that you know can be worn with everything (navy, grey and camel are excellent choices), or opt for a patterned take in a muted palette. You can’t go wrong with a Black Watch tartan scarf, for example, made up of a deep green, blue and black check.
Fabric choice is imperative too. You want something soft and comfortable that doesn’t agitate your skin, so try a merino wool, knitted cotton or cashmere-blend version.
Aside from a scarf, the usual suspects come into play, namely gloves and a beanie. There are a multitude of options for the former – leather, wool, technical styles, mitts – so simply opt for a pair that best suits your needs and aesthetic.
The beanie isn’t a one-season accessory, so you want to ensure versatility. There are a wealth of options available on the current market but for our money a minimal navy fisherman design in a ribbed cashmere blend is a foolproof option that will get good use for nine months of the year. Not only will it complement everything in your existing wardrobe, the softness of cashmere will ensure it doesn’t itch the top of your forehead, too.
30 winter outfit ideas for men
Smart casual grey overcoat
The grey overcoat is a classic piece of winter outerwear. Go for one with a bit of texture in the weave and it’ll work admirably as both a smart jacket for work and something you can wear on weekends with jeans.
Here, we hit somewhere in the middle, with the tonal grey shirt, straight-leg black chinos and black penny loafers creating a sleek business-casual look that works in and out of the office.
The alternative colour puffer jacket
You’d struggle to walk down any city street in winter and not spot someone wearing a puffer jacket. The 90s fashion essential has come back in a big way, and for good reason. It’s incredibly practical, with its weatherproof outer shell and quilted or down-filled lining ensuring you stay toasty and dry, come rain or snow.
Go for one in a seasonally appropriate shade like green, burgundy or orange and contrast it against a dark black base, as shown here, to let it become the focal point of your look.
As we know by now, one of the more interesting ways to dress for winter is by playing with colour. There’s a number of ways you can approach this, from purposefully clashing statement shades through to more understated colour matching.
For the latter, try to link colours between garments, as shown above. Here, the coat features multiple hues in its check pattern, including grey, navy, burgundy and orange. The clever part comes through the choice of garments layered underneath: a light blue shirt picking out navy and the bright orange-red sweater highlighting the other prominent shades.
It’s an advanced level menswear move that subtly ties an outfit together and lets you stand out for all the right reasons.
Monochrome winter outfit
You can’t go wrong with a monochrome fit, regardless of the season. Mixing and matching black and white pieces is foolproof and saves time each morning. Particularly helpful when you can’t afford to have your heating on and you want those extra few minutes in a nice warm bed.
However, such a limited colour palette can sometimes fall a bit flat. Not so in winter, where the extra layers required allow you to create depth and visual interest via contrasting silhouettes and textures, as shown here.
Slim black twill pants and a knitted quarter-zip sweater is broken up nicely by a bright white tee, while the long-length quilted parka and chunky military boots brings some weight to the overall look.
Earth tone winter outfit
If you’re looking to break away from the safety of dark colours this winter, use this outfit as a template.
By sticking to earthy shades of white, brown, green and cream – all of which naturally complement each other – you can create statement looks with very little thought.
Here, the outdoorsy palette is reinforced by outdoorsy pieces – slim off-white cargo pants, a chunky cream roll neck, a padded workwear jacket and brown leather hiking boots – giving the entire outfit a sense of authenticity while remaining entirely practical.
Smart winter turtleneck
You won’t regret buying a turtleneck this winter. Whether you go for a chunky lambswool version or a lightweight merino take, it’s an incredibly versatile piece that’ll work with both your smart and casual wardrobes.
Combine it with tailored moleskin chinos and rubber-soled Oxford shoes for a sleek and sophisticated look that’s perfect for the office or a fancy restaurant date.
Heavyweight work shirt with an overcoat
While a knit might be your first choice for a mid layer, don’t discount heavyweight work shirts. Whether in the form of a CPO-style shirt or a chore coat, these adaptable garments are excellent layering pieces, especially when worn under heavier overcoats or puffer jackets, as shown here.
Elsewhere, black sweatpants and retro runners up the comfort factor while contrasting against the smartness of the top coat, making it an excellent example of high-low dressing.
Corduroy trousers & workwear staples
While chinos are a spring- and summertime staple, corduroy trousers make the perfect substitute in winter. The fabric is both soft and warm, boasting plenty of texture that’ll help boost even the simplest of fits.
Wear yours like you would khaki pants, with workwear staples such as a Henley top and checked flannel overshirt.
Winter office attire
In winter, the easiest way to refresh your 9-5 look is through your choice of outerwear. Particularly if you’re otherwise limited by a strict office dress code.
A smart check overcoat is a stylish choice that will stand out against a sea of black and navy versions on the morning commute. Go for a simple Prince of Wales motif in grey or brown, or a Black Watch tartan design, and wear it over your lounge suit or business-casual separates to instantly look like more of a boss.
Carpenter pant with a hoodie and puffer jacket
When looking to update your winter wardrobe it’s easy to gravitate towards the more exciting cold-weather pieces, such as knitwear and outerwear. But overlook legwear at your peril. Winter-weight trousers can make all the difference to your comfort levels when the mercury drops and you need something more robust than your lightweight cotton chinos.
If we could suggest just one pair of pants to invest in this season it would be a carpenter style. Traditionally cut from a durable cotton canvas or denim, they’ll keep you warm while bringing a rugged, workwear edge to your everyday attire.
Wear them as you would your favourite pair of jeans, combining with sweats, sneakers, heavyweight shirts and your favourite jacket.
Classically heritage pieces
No matter the season, it’s difficult to go wrong if you stick to menswear classics in neutral colourways. This outfit combines dark blue jeans, a chunky ribbed knit, a denim shirt and camel coat to create a foolproof getup that looks good on all men, no matter your age.
Finish with brown leather Derby boots and you’re ready for whatever Mother Nature throws at you.
Lightweight winter layering
When winter bites, it’s all too easy to just throw on a big coat and be done with it. But it’s not exactly the most creative way to tackle to the cold.
Instead, consider dressing like you would in fall and layering multiple lighter-weight pieces to create the necessary protection against the elements.
The above is a prime example of how to pull this off: a classic white cotton tee, heavyweight black hoodie and thick flannel overshirt is plenty warm enough for all but the coldest days of winter, and ideal for dealing with fluctuating temperatures – such as moving from outdoors into a centrally-heated building.
If you need some extra ballast, try introducing a thin merino wool base layer or switching the T-shirt for a thermal version (something like Uniqlo’s HeatTech range).
Fleece jacket and work pants
It’s gone from a widely ridiculed piece of hiking wear to one of the most lauded winter essentials for 2023. Yes, fleece jackets – the type your dad has been wearing for decades – have enjoyed a huge resurgence recently, thanks in part to the 90s and 2000s trend, as well as the fact that they are both warm and practical.
Take it out its usual context and wear yours in a more skate/streetwear-inspired fit such as this, combining it with khaki twill work pants, a heavyweight T-shirt, ribbed beanie and canvas high-tops. It’s a look your old man wouldn’t be caught dead in. (And that’s a good thing.)
High-low winter dressing
High-low dressing is one of the best ways to tackle winter weekends, combining the sophistication of tailoring (high) with the comfort of sportswear (low). However, this juxtaposition can appearing jarring if you don’t reduce the gap in formaility.
To do this, take the tailored pieces down a notch by either opting for rugged fabrics (flannels, textured wools, corduroy) or more relaxed fits, then elevate your casualwear by going the opposite way, using luxury fabrics (think merino wool or cashmere) and slimline cuts.
The above outfit is a prime example: the trousers have a sharp crease down the centre but the loose fit and pooling at the ankles reduces how smart they appear, meaning the chunky sneakers don’t clash. Similarly, a fitted merino wool turtleneck is contrasted by the bulky puffer jacket, giving balance to the upper half.
Oversized knitwear and jeans
For ultimate comfort, and those times when you just want to bundle up, boxy, relaxed fitting knitwear is hard to beat. Whether you go for a fisherman’s sweater, shawl neck cardigan or chunky roll neck, a slightly oversized version will look great with every type of pants you own, from jeans and cords through to tailored chinos and pleated trousers.
Keep the rest of the look restrained to let your knit become the focal point, then throw a raglan sleeve overcoat on top when the weather turns. Cosy, effortless winter style.
Brown with denim
Brown and blue is a classic colour combo that works for almost all skin types, and one you’d be wise to try this winter.
Although navy is considered more seasonally appropriate, there’s no reason why you can’t break out your light wash jeans during the colder months. They complement the full spectrum of brown shades, from camel to chestnut, as proven above, while denim will keep you adequately protected from the elements.
Camel and black
Camel and black is another all-time great menswear colour combo that oozes sophistication.
A camel coat is a lifetime piece – especially if you go for a classic, heavy wool duffel or overcoat – so it pays to invest wisely. Once you’ve found the perfect version, you should be looking to wear it with black jeans or trousers at every opportunity.
Here we go for the former, creating a soft colour transition via the tonal cream hoodie.
Hoodie with a slouchy overcoat
This outfit represents one of the easiest ways to dress for winter. It’s incredibly simple, balancing classic, heritage menswear with the comfort of sweats.
Keep it tonal with a grey top half, courtesy of a charcoal micro check overcoat and grey cotton jersey hoodie. Ensure the coat is relaxed and unstructured, with shoulders that follow the natural line of your own, so it doesn’t jar in formality.
White jeans are a confident choice that look great against the darker backdrop of winter, but you can easily switch them out for your favourite indigo selvedge denim and the look still works.
Finish with classic canvas high-tops and you’ve got a daily getup that’s both comfortable and stylish.
Winter-ready parka jacket outfit
There are two kinds of parka: the lightweight fishtail variety, and the heavy, explorer-ready design. For winter, the latter has your back (figuratively and literally), keeping you warm, protected and stylish no matter the weather.
As this is clearly a practical outerwear choice, pick a versatile colourway and don’t overthink the styling: chuck it on over everything from a full suit to chinos and a crew neck, as shown here, and let it do its job. Perfect for your own urban expeditions.
Elevated winter grunge outfit
The overcoat has long been considered a smart, tailored piece of outerwear, primarily designed for wearing with a suit or trouser and blazer separates. However, contemporary designers have transformed the silhouette into something much more versatile, cutting it with dropped shoulders that have little to no padding.
These type of coats can be dressed up or down to suit the occasion and your mood, as this outfit clearly demonstrates. A base look of black jeans, a Henley shirt, beanie and chunky Chelsea boots has an edgy, grungy feel to it, yet the overcoat doesn’t jar against this backdrop. In fact, if anything, it elevates and sharpens up the overall aesthetic.
Casual winter outfit
For an easy, everyday casual winter fit, try a heavyweight black parka with a tonal zip-up hoodie, as shown here.
Finish with your trusty khaki pants and minimal white sneakers and you’ll be as comfortable as you are stylish for a day running errands.
Winter-ready cropped jacket
You don’t have to default to long coats and bulky down outerwear in winter. A cropped jacket can prove just as effective, so long as you pick the right design, as shown here.
This blouson is ready to tackle the cold thanks to its heavyweight wool construction and large shearling/borg collar, which can be flipped up for added wind protection.
You wouldn’t want to be caught wearing it in a downpour, sure, but the short silhouette affords you more layering options on those dry but bitterly cold days. Here, an easy all-black fit sets a slick base against which the rich check pattern can shine.
Structured winter overcoat outfit
While softly padded overcoats might be the most adaptable choice, sometimes there’s just no beating a seriously sharp, structured overcoat. Especially for formal occasions or times when you need to look ready for business.
Go for one in camel and wear it with your entire tailoring collection, from navy suits through to grey wool separates.
Introduce some winter colour
Dressing for work doesn’t typically allow for much creativity, particularly if there’s any form of dress code. So how can you stand out against your contemporaries to give yourself an edge? It’s a balancing act the average man tends to get wrong, resorting to garish socks or ‘humorous’ ties. But sometimes all that’s required is a subtle injection of colour.
Try, for example, a timeless navy blazer/grey trouser separates combo with a deep green turtleneck in place of a shirt. As you can see above, it looks smart and professional, but you’ll instantly separate yourself from the rest of the rat race.
Statement winter outerwear
If you’re unsure of where to start with colour, or simply not confident stepping outside your monochrome comfort zone, a coat in a striking hue can be the easiest way to breath life into your daily getups.
After all, you only wear your outerwear for short periods of time when outdoors, meaning you can keep your outfit underneath simple and restrained – as shown here – and let your coat do all the work.
Tonal navy winter outfit
All black everything might be the default setting for tonal dressing, but don’t sleep on navy. This classic hue flatters the majority of body types and skin tones, and looks extremely modern when worn head to toe.
As with black, to pull it off successfully you need to create contrast between each piece using texture and tone. The above is a great example of getting it right, with the dark navy wool overcoat, deep blue cashmere turtleneck and grey-blue raw denim jeans working harmoniously without blending into each other.
The tan suede boots meanwhile add the perfect punctuation mark to this versatile and contemporary fit.
Classic American style is not to be messed with. It looks cool in virtually any situation, whether you opt for a smart preppy aesthetic or something rugged and outdoorsy.
This outfit is firmly in the latter camp, combining a number of traditional workwear staples – flannel shirt, selvedge jeans and work boots – with an on-trend green fleece jacket and cool round-lens sunglasses for a masculine look that manages to feel classic and contemporary at the same time.
It’s all about the scarf
This is a prime example of how accessories can elevate a look. The jacket, sweatshirt, jeans and boots combo is fine, sure, but the scarf’s pop of colour lifts the aesthetic and brings everything together, making it far more than the sum of its parts.
Going out out
For an evening party look, or dressing for a night out, black will never let you down. Yet while it’s easy to pull together an all-black fit that looks sharp, the trouble in winter is deciding which coat to wear with it.
A slick black overcoat can be a touch too severe, which is where the parka comes in. Throw a lightly padded version over a roll neck and tailored trouser pairing, like above, and it’ll keep you warm while stopping things from looking too funereal.
Winter double-breasted overcoat
Make ours a double. While single-breasted overcoats are far more popular, don’t discount double-breasted designs. Traditionally considered the most formal outerwear style you can wear, go for one with slouchy shoulders and little to no padding and it can be dressed down with smart casual staples, as shown here, or thrown over your razor-sharp tailoring during the working week.
It will quickly become part of your daily armour throughout winter, offering a superb return on investment.