A proper winter outfit must contend with cold mornings, dark afternoons, and the persistent chill accompanying the season’s often grey skies.

As winter may not be the cheeriest time of year, but it’s still an excellent opportunity for those with a keen fashion sense to explore and enjoy a sartorial playground.

So, let me guide you through several winter outfit ideas I’ve handpicked, perfect for various occasions, from formal business environments to casual weekend outings.

Navy Suit with Overcoat for a Corporate Office

Nothing speaks more of professionalism for a formal business setting than a classic navy suit.

On the other hand, a navy overcoat is a versatile piece in your winter wardrobe that effortlessly complements the suit.

navy overcoat with a navy suit and white shirt

A white button-up shirt and navy tie keep the look crisp and clean.

Winter footwear is key to nailing this outfit. Keep it classy and traditional with black cap-toe Oxford shoes, or opt for black dress boots for those extra cold days.

Charcoal Suit with Black Overcoat

The charcoal suit presents an equally dressy alternative. It’s a staple every man should consider alongside the essential navy suit.

black overcoat with a charcoal grey suit

The ensemble maintains and elevates its formal elegance with a sleek black overcoat. This coat-over-suit pairing is particularly apt for formal events.

The centerpiece of this outfit is undoubtedly the tie. You can opt for a grey print tie, perhaps adorned with a subtle yet intricate paisley pattern.

However, solid black or navy ties could also work.

The best way to complete this look is with polished black Oxford shoes. Their simplicity ensures the tie’s unique charm remains the outfit’s standout feature.

Grey Cashmere Suit with Button Down Shirt

Embrace a more casual look with a grey cashmere suit. The soft texture of cashmere lends itself well to less formal occasions.

grey suit, white shirt, and brown loafers

The inclusion of the jacket’s ticket pocket and notch lapels add to the suit’s relaxed charm.

Complement this suit with a white dress shirt and a dotted purple tie for a pop of color. If you want to dress down even more, change for a button-down and forgo the tie.

Brown loafers work brilliantly here, especially in a suede texture. This outfit is perfect for semi-formal events or a business-casual office environment.

Sleek Trench and Tie Ensemble

A trench coat over a suit is a classic combo that has withstood the test of time.

navy trench coat, suit, and light blue dress shirt

It looks absolutely astonishing and provides functionality for the modern gentleman to tackle inclement weather.

Wear a light blue dress shirt and a navy tie underneath to create a cohesive look.

Break the monochrome palette with brown suede loafers. Then, give the perfect finishing touch with a silk pocket square.

Olive Raglan Coat & Turtleneck Harmony

Embrace a blend of formal and casual styles with an olive green raglan coat.

green raglan coat, grey turtleneck, and grey dress pants

This coat style, known for its unique sleeve construction, suits various body types and occasions.

Pair it with a grey chunky turtleneck and grey dress pants, which you can cuff for an impeccable fit.

Let the dark brown tassel loafers truly shine and showcase your dapper personality.

Grey Shearling & Charcoal Wool Blazer

The centerpiece is your luxurious grey shearling jacket. It’s an excellent outer layer for blistering cold days.

grey shearling jacket and charcoal blazer over grey turtleneck

Beneath a charcoal wool blazer, while a grey turtleneck forms a sleek base. A glimpse of a white dress shirt adds a classic, layered warmth, ready to shift to a more formal mode if required.

The charcoal jeans offer a relaxed counterpoint to the upper part.

Grounding the look are robust brown leather work boots designed to easily traverse winter’s demands.

Suit & Chelsea Boots

In the pantheon of men’s footwear, the Chelsea boot stands as a paragon of enduring style.

black overcoat, navy suit, and black chelsea boots

Traditionally partnered with casual denim, these boots have stylishly transitioned to complement the refined lines of dress pants as well.

When donning this ensemble, pay careful attention to the pant tapering and hem break for a flawless silhouette.

A sleek overcoat and a navy paisley scarf artfully contrast and enhance the suit’s hues.

Pop of Color with Burgundy Tie

Brighten up a winter day with a pop of color. Pair a navy trench coat with a white dress shirt and a bold burgundy tie.

navy trench coat, white shirt, burgundy tie, blue pants, and black derby shoes

This splash of color adds warmth and vibrancy to an otherwise dull winter outfit.

Blue dress pants continue the color theme, while black Derby shoes maintain the outfit’s formality.

This ensemble is perfect for those who want to stand out in a professional setting while keeping their look tasteful and season-appropriate.

Brown Plaid Suit with White Parka

Embracing the winter season’s offerings, a brown plaid suit becomes the canvas for textural play.

white parka, brown plaid suit, off-white polo shirt, and dark brown boots

Layered atop a white parka with its sturdy construction and insulating prowess.

The off-white polo sweater underneath keeps the outfit casual, while the brown casual boots add a rugged touch.

Textured Greys and Rugged Boots

Embrace the winter season with an outfit that plays with textures and tones.

grey puffer jacket, knit turtleneck, and jeans with dark brown boots

A grey puffer jacket, knit turtleneck, and jeans create a cohesive and stylish monochromatic look.

Dark brown casual boots add a necessary contrast and a practical element to the outfit.

This ensemble is ideal for casual weekends or relaxed evenings out.

Winter Ivy League Outfit

Start with a classic denim jacket and layer it over a charcoal argyle patterned sleeveless jumper to add a preppy twist reminiscent of Ivy League style.

denim jacket, charcoal jumper, white shirt, and brown loafers

If the jacket feels too thin for the current weather, you can always swap it with a classic navy pea coat.

Underneath, a crisp white dress shirt provides a sharp base that complements the structured denim and patterned knitwear.

Finish the look with a pair of tailored grey trousers. This creates a smart contrast with the relaxed denim.

Maintain the vibe with classic medium-brown penny loafers.

Creamy Knits and Tailored Trousers

Aran sweaters are unique and standout pieces for winter outfits.

The softness of the knitwear contrasts beautifully with the structured look of beige dress pants.

beige overcoat and pants with off-white turtleneck and boots

White casual boots add a modern and unexpected twist to the ensemble, blending seamlessly with the lighter tones of the outfit.

This look is perfect for those who appreciate a refined, minimalistic aesthetic.

Navy Blazer with Charcoal Pants

Navigating the corporate landscape with style requires a deft touch, particularly when a dress code is in play.

navy blazer, brown gingham shirt, and brown leather loafers

Start with a stylish navy blazer and charcoal pants combination.

Pair it with a brown gingham shirt and a coordinating brown tie for warmth and texture.

Finally, the ensemble is impeccably completed with dark brown penny loafers.

Light Brown Casual Suit with a Shearling Jacket

This winter outfit marries the rugged elegance of a navy suede shearling jacket with the crisp tailoring of a casual beige suit.

navy shearling jacket, beige suit, navy sweater, and brown boots

With its sumptuous shearling collar and soft suede, the jacket offers a luxurious feel and formidable warmth. It pairs effortlessly with the suit’s relaxed yet smart cut.

The navy sweater underneath ensures extra coziness and a seamless color flow.

Completing the look, the dark brown combat boots add a practical touch with their sturdy build.

Pea Coat over Charcoal Textures

If the thought of diving into a kaleidoscope of colors for your wardrobe leaves you a tad hesitant, let a standout coat be your savior.

cream pea coat and a charcoal turtleneck, off-white sweater, and grey trousers

A coat like this creamy beacon of style lifts your outfit and carries it with an air of effortlessness. It’s this piece that does the heavy lifting style-wise, allowing you to keep everything else low-key.

A cozy charcoal turtleneck paired with crisply tailored trousers, all tied together with those cream derby shoes that whisper casual luxury.

Olive Flight Jacket with Off-White Trousers

Here’s a look that’ll turn heads and ward off the winter blues.

It starts with a dark green bomber jacket, sporting a generous shearling collar that’s as much about style as it is about staying toasty.

dark green bomber jacket with a half-zip sweater and off-white trousers

The jacket’s dark hue is the perfect foil for the lighter shades beneath, with a half-zip sweater in a harmonious shade of green.

Then, those off-white dress pants, clean and crisp against the darker tones.

Tie it all together with a pair of light brown boots. This look is ready for the office or a weekend jaunt, proving that winter fashion doesn’t have to be dreary.

Blazer & Gilet Pairing

Sleek and casual, this outfit bends the rules of traditional office wear into something more relaxed and composed.

grey blazer and gilet with white turtleneck and navy pants

In its muted grey tone, the structured blazer effortlessly complements the zippered turtleneck. While the trousers, in textured navy, break the mold.

Then there’s the grounding element: a pair of dark Chelsea boots. A suede material and muted color blend understated luxury with functional style.

Cardigan Jacket Over Dress Shirt

This ensemble is a tactile feast, blending classic knitwear’s smoothness with a well-chosen shirt’s crispness.

black quilted cardigan jacket, light blue shirt, and charcoal pants

Here we have a black quilted cardigan, a versatile piece that can easily pivot from a smart casual Friday to a relaxed Sunday brunch.

Peek beneath, and the light blue of the dress shirt comes into play, its classic pattern providing a subtle yet engaging contrast.

And let’s not overlook the bottoms; the charcoal pants and brown leather sneakers effortlessly straddle the smart-casual divide.

Fair Isle Pattern Vibes

The navy Fair Isle sweater is the real MVP here, dishing out those cozy vibes with a pattern that’s been a winter go-to since your granddad was a lad.

navy sweater over blue dress shirt, charcoal pants, and dark brown dress boots

It’s laid over a crisp, light blue dress shirt that peeks out, giving a nod to the workweek without screaming 9-to-5.

When it comes to bottoms, the charcoal trousers keep things looking sharp and on point.

The dark brown boots are like the cherry on a stylish cake.

Perfect for sipping something hot or striding into a weekend adventure.

Shearling Jacket & Boots

Rock a brown shearling jacket oozing with vintage pilot vibes like a champ.

brown shearling jacket with charcoal pants and brown dress boots

It’s the kind of jacket that keeps the cold out and brings the style in. Underneath, keep it simple with a classic white t-shirt.

But then, bam, the navy cardigan adds a subtle layer without trying too hard. Slide down to those charcoal dress pants, and it’s a smooth transition to smart town.

The brown dress boots are the full stop at the end of a well-dressed sentence, tying everything together with a touch of old-school cool.

This isn’t just an outfit; it’s a whole mood for those crisp days when you want to look hot in the cold.

Corduroy Chore Coat for a Rugged Style

Corduroy chore coats are the unsung heroes of the texture game.

dark brown corduroy coat and chelsea boots

Swap out the usual twill for this velvety, ribbed fabric, and you’ve got a classic look and a cut above.

Throw on with some charcoal trousers, and you’re onto a winner.

It’s a subtle nod to the workwear trend without going full lumberjack – a bit retro, a little academic, and totally on point.

Dapper Loafers

This dark grey knitted blazer blends the snug feel of a cardigan with the sharp tailoring lines; it’s like your favorite comfort food got a Michelin star.

Dark grey cardigan with black turtleneck, pants, and loafers

Underneath, there’s a smooth and sleek black turtleneck; it’s the secret weapon of layering.

And those black loafers are the final touch, as classic as a vinyl record but as fresh as your latest playlist.

Put it all together, and you’ve got a look that’s as easy as Sunday morning but ready for Monday’s boardroom battle.

Overcoat with White Leather Sneakers

The overcoat’s the piece you reach for when the chill sets in. Layer it over a soft blue sweater and beige chinos for a set of clothes made for each other.

navy overcoat, blue sweater, off-white chinos, and white sneakers

Make fabric set them apart. Play with something rich in texture, promising not just warmth but a kind of everyday luxury.

Whether you’re dashing between meetings or stepping out on a crisp weekend morning, this overcoat is less a choice and more a statement.

Hoodie and Jeans

Check out this ensemble – it’s got that “just threw it on” look, but every piece says something.

beige overcoat, cream hoodie, black jeans, and black chelsea boots

The hoodie is the comfort piece but in a shade ready to slide under that sharp overcoat. The jeans keep it real, and those boots are the silent type that means business.

Top it off with a beanie, and you are ready to stroll down the street.

Houndstooth Coat Over Suit

This ensemble pairs a classic tan houndstooth overcoat with a striking burgundy suit for a bold contrast.

burgundy suit, tan turtleneck, and tan Chelsea boots

The outfit is softened by a coordinating tan turtleneck beneath the suit.

Finishing the look, tan Chelsea boots mirror the overcoat, creating a cohesive and stylish outfit ideal for the winter months.

Things to Consider

When dressing for winter, several key factors ensure both comfort and style.

It’s not just about piling on clothes; it’s about thoughtful choices that enhance your winter outfit while providing the necessary warmth.

Embrace Layering

Layering encapsulates the essence of winter fashion. It begins with selecting a base layer, a luxe thermal, or a sleek turtleneck.

basic layering

Next comes the primary layer, a substantial piece like a crisp cotton shirt or a soft, ribbed sweater. This layer acts as the outfit’s focal point for the winter.

The final flourish is the outer layer, ranging from a structured woolen overcoat to a modern technical jacket with a more urban edge.

brown overcoat: old money style

The magic of layering lies in the harmony of colors and the interplay of textures.

Think of a smooth turtleneck or chunky cable-knit sweater topped with a herringbone wool coat.

different forms of layering

Each piece complements the other and stands ready to be peeled off or piled on as the indoor and outdoor temperatures dictate.

Footwear Choice

When curating winter outfits, your choice of footwear is incredibly important.

The right shoes are crucial for tackling the elements; they anchor your style and shield you against the cold and wet.

black vs. brown Chelsea boots

Invest in handcrafted shoes or boots, often featuring robust leather uppers and chunky rubber soles.

Look for designs with water-resistant storm welts to ensure dryness and comfort even when the weather turns foul. Remember, practicality doesn’t have to sacrifice style.


Accessories are not just an afterthought in winter; they are essentials.

Hats, scarves, and gloves are necessary for warmth but also offer an opportunity to add personality to your outfit.

Choose items that coordinate with your overall look, whether a bright scarf for a pop of color or a sleek leather glove for a more refined appearance.

Remember, accessories can elevate any winter outfit from ordinary to exceptional.

Alexander Stoicoff

Author: Alexander Stoicoff

Hi, I’m Alex, and I’ve studied and specialized in styling in Rome. Through my writing, I want to help men dress well and learn the purpose and significance of suits and other formal attire. My final goal is to make men more confident in their wardrobe choice and life in general.