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Overshirt Outfits for Men

Overshirts are taking over, becoming a staple on the streets and a favorite among the style-savvy.

Yet, amidst their rising fame, many are still puzzled by how to wear these adaptable layers correctly.

Different overshirt outfits for men

If you’re uncertain about what an overshirt can do for you, fret not – you’re in the right place.

With the overshirt’s casual style and knack for sharp sophistication, we’ll give you twelve different outfit inspirations to craft a polished look.

Inspired by Mother Nature

Green checked overshirt, green t-shirt, khaki jeans, and white sneakers outfit

Stride confidently into the season with a green checked overshirt layered over an earthy green tee.

Khaki jeans anchor the look, their tailored cut speaking to a man who knows his business, be it a casual Friday or a weekend escapade.

And what’s not to love about those pristine white sneakers?

They are the exclamation point to this understated style.

Steve McQueen Approved

Light gray shacket, white hoodie, brown trousers, and brown hiking boots outfit

We’re looking at a light gray shacket, a piece that’s as at home on city streets as it would be on a cinematic chase through San Francisco.

Wear underneath a white hoodie that adds extra warmth and a hint of streetwear edge.

The trousers and hiking boots are a rich, dark brown, a color that evokes the rugged elegance of vintage leather, cut to a contemporary silhouette that McQueen himself would approve of.

Dress Better in 2 Minutes

Navy overshirt, white t-shirt, navy drawstring trousers, and navy sneakers outfit

Elevate your style in the time it takes to tie your shoes with this impeccably tailored navy overshirt.

Wear it with a classic white tee, a garment that acts as a blank canvas, and navy drawstring trousers for a refined casual touch.

Slip into a pair of matching navy sneakers for the finishing touch.

This is your two-minute transformation to a man who’s ready for anything, from a casual coffee run to a spontaneous night out.

Wear a Shirt Jacket with a Turtleneck

All black outfit with overshirt, turtleneck, jeans, and Chelsea boots

When layering like this, it’s essential that the turtleneck is made of a thinner material; think a soft jersey cotton or a fine wool blend.

This ensures a sleek profile under the overshirt, allowing for a clean, structured look without any added bulk.

Anchoring the look are the black Chelsea boots – timeless, with a hint of rock ‘n’ roll edge, they’re a nod to the iconic mods of the 60s while completely grounding the outfit in the now.

Fly AF

Wear a gray overshirt, navy crew neck t-shirt, off white drawstring trousers, and white sneakers

Sartorially speaking, our gentleman here is soaring high with a look that’s undeniably FLY.

The light gray overshirt is a breathable, stylish and smart layer.

The off-white drawstring trousers are the pièce de résistance, marrying comfort with a sharp, tailored aesthetic, ideal for the man on the move.

And those white sneakers? They’re the finishing touch.

Ready for a city stroll?

Celebrities Wear It

Navy overshirt, white t-shirt, gray drawstring trousers, and white sneakers outfit

Emulating the effortless cool of style icons, we are stepping out in a navy overshirt, a staple that’s garnered the approval of the likes of Ryan Gosling and David Beckham.

And it’s clear why – it’s not just a fleeting trend.

It introduces a subtle contrast with cuffed gray drawstring trousers.

Elevate Your Look with Patterns

Navy violet plaid overshirt, white and blue button-down shirt, navy chinos, and beige sneakers outfit

Patterns are the secret spice of the fashion world, and our gentleman exemplifies how dapper they can make you look.

He’s paired a navy and violet plaid overshirt with a white and blue checkered button-down shirt, a masterclass in mixing patterns without overwhelming the senses.

The navy chinos are the solid base that grounds the outfit, their classic hue providing a perfect backdrop for the patterns to shine.

Topped off with beige sneakers, the ensemble walks that fine line between casual and fashion-forward.

Neutral Tones for Fall

Light brown brushed overshirt, white crew neck sweater, brown corduroy trousers, and brown hiking boots outfit

In the tapestry of modern menswear, neutral tones weave an eloquent narrative of understated elegance.

They’re the sartorial equivalent of a quiet conversation instead of a shout across the room.

The look here is a testament to that philosophy, where the light brown brushed overshirt whispers autumnal charm.

Whether stepping out for a casual coffee or clocking in for a day at the office, this is the perfect outfit idea for you.

Fresh and Clean

Blue overshirt, green plaid shirt, green corduroy jeans, and brown casual boots outfit

The blue overshirt is a stylish comrade to a well-curated wardrobe.

Worn over a green plaid shirt that peeks out with a hint of playfulness.

This gentleman’s attire is grounded with corduroy jeans, adding a textural contrast that’s visually appealing.

And let’s not overlook the boots, a sturdy pair ready to tread any path, a reminder that style and durability can indeed walk hand in hand.

Read more: green pants outfits.

Rugged Charm

Wearing a brown overshirt, green plaid shirt, brown jeans, and brown suede Chelsea boots

Meet the go-to for those crisp mornings and the sharp chill of twilight: the heavyweight flannel overshirt.

This isn’t just any layer; it’s the soft embrace of comfort that comes with a rugged charm, easy to slip over an everyday shirt.

The travel jeans are a thing here, designed to move with you.

And those brown suede Chelsea boots? Ah, come on.

Best Dressed in Town

Green overshirt, beige t-shirt, cream jeans, and casual boots outfit

You know the secret lies in the balance – light with dark, soft with structured.

The palette is a nod to nature’s canvas, hinting at an adventurous spirit still firmly planted in urban style.

The key here is in the details.

The subtle cinch of a matching belt defines the silhouette or the choice of boots that tell a story of many miles.

This isn’t just dressing; it’s a narrative woven through each choice.

Each layer tells the world that the best-dressed man in town knows the power of understatement.

Lumberjacket Overshirt

Lumberjack brown overshirt, gray turtleneck, black jeans, and brown casual boots outfit

The lumberjack overshirt bridges the ruggedness of the wilderness and the sleek lines of city fashion.

The tip here is to let such a piece lead your outfit.

Wear it with understated essentials that don’t compete but complement.

Things to Consider

When considering an overshirt’s inclusion in your ensemble, consider its fabric and weight.

An overshirt should act as a versatile layer.

Its suitable for a crisp autumn day or as an added layer in the cold weather.

It’s the bridge between indoor and outdoor attire, so choose a material that complements the climate and occasion.

Fit and Layering

An overshirt is designed to be worn over other garments, so its fit is crucial.

Proper fit and layering possibilities of the overshirt

It should be roomy enough to accommodate a shirt underneath yet tailored sufficiently to maintain a sharp silhouette.

Remember, the goal is to achieve a look that’s effortless and layered without adding bulk, so consider the fit of what you’ll wear underneath as well.

Color Coordination

The color of your overshirt can be a statement or a subtle inclusion to your outfit.

David Beckham wearing an overshirt

Neutral tones offer flexibility and longevity, easily paired with other items in your wardrobe.

If opting for a patterned or brighter color, ensure it harmonizes with your existing pieces.

Occasion Appropriateness

Finally, assess the occasion.

Occasions appropriate to wear an overshirt

An overshirt can range from workwear-inspired ruggedness to a more refined, office-appropriate garment.

The key is to match the style and material of the overshirt with the setting, be it casual, smart casual, or somewhere in between.

Your overshirt can be a versatile workhorse, but only if it aligns with the dress code of your destination.

Roger Grinstead
Roger Grinstead

With 25 years in the fashion industry, Roger Grinstead is a senior designer at X2U. His expertise spans menswear, womenswear, and product development. Outside designing cutting-edge garments, Grinstead channels his passion for style into writing about men's fashion and hairstyles. His multifaceted perspective brings a unique depth to the world of fashion.

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