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Sweater Over Dress Shirt Outfits for Men

Elevate your style game with the classic pairing of a sweater over a dress shirt.

A staple in men’s fashion, this layered look brings together comfort and class, ideal for any setting.

Different sweater over dress shirt outfits for men

Join us as we showcase a carefully curated list of over 20 outfits to get inspired.

Navy Sweater Over White Dress Shirt

Navy sweater over white dress shirt, light blue denim jeans, and brown suede Chelsea boots outfit

Garbed in a navy cable knit sweater layered over a white dress shirt, this casual yet polished look is ready to impress.

The ensemble is neatly rounded off with a pair of brown suede Chelsea boots and light blue denim jeans, blending comfort with a touch of sophistication.

Blue Zip-Front Cardigan Sweater

Blue zip front cardigan sweater, white dress shirt, navy chinos, and black double monks outfit

Sporting a sophisticated blue zip-front cardigan layered over a crisp white dress shirt.

Additionally, this modern look is paired with tailored navy chinos.

Finish off elegantly with a pair of black double monk strap shoes, offering a seamless blend of casual and dressy elements.

Patterned Sweater Vest

Navy sweater vest, blue dress shirt, navy tie, charcoal dress pants and dark brown dress boots outfit

Rock a navy sweater vest over a crisp blue shirt paired with sleek charcoal pants.

Finish with classy dark brown boots.

A modern twist on classic vibes!

Rich Brown Tones

Light brown half zip sweater, white dress shirt, brown dress pants, and dark brown penny loafers outfit

A soft light brown half-zip sweater drapes gracefully over a sharp white dress shirt, striking the perfect balance between comfort and sartorial finesse.

The rich brown trousers provide a smooth transition down to the classic dark brown penny loafers.

This crafts a look that’s as appropriate for a day at the office as it is for a relaxed weekend brunch.

Navy V-Neck Sweater

Navy v-neck sweater, multi-color shirt, gray dress pants, and brown derby brogues outfit

The multi-color checkered shirt offers a touch of prep-school chic without trying too hard.

Another intricate element is the robust brown derby brogues.

It’s an outfit that embodies a confident man who values a sharp yet understated approach to his wardrobe.

Preppy Looks

Green sweater, pink dress shirt, khaki jeans, and navy sneakers outfit

This outfit is a playful twist on the classic preppy look, infusing a dash of daring with its vibrant green sweater atop a soft pink dress shirt.

The ensemble is casually grounded by distressed khaki jeans, a nod to a more relaxed, adventurous spirit.

Navy sneakers add a contemporary edge, proving that a little spice in your wardrobe can go a long way in crafting a look that’s both fresh and familiar.

Iconic Fair Isle Sweater

Wearing a blue fair isle wool sweater, light blue dress shirt, charcoal gray dress pants, and dark brown lace-up boots

The Fair Isle sweater, with its intricate pattern of blues and traditional design, brings a touch of heritage to a modern silhouette.

This woolen piece, layered over a light blue dress shirt, offers a rich contrast against the clean lines of the charcoal gray dress pants.

The outfit is anchored with dark brown lace-up boots, adding a rugged yet polished finish.

With Bomber Jacket

Bomber jacket, cable sweater, dress shirt, and black shoes outfit

There’s something about a bomber jacket that just makes you feel stylish and confident.

Layer it with a dark brown cable V-neck sweater and a light blue plaid dress shirt.

Finish the ensemble with a pair of black leather brogues, a dark tie, and a dark brown leather belt.

With a Navy Double-Breasted Blazer

Double-breasted blazer, crew neck sweater, dress shirt, and suede loafers outfit

A double-breasted blazer is a must-have piece in every men’s wardrobe.

A beige crew-neck sweater and light blue dress shirt will elevate your look.

Additionally, pair navy pants with brown shoes to complete this outstanding style.

Brown Shawl Cardigan Sweater over Blue Chambray Shirt

Brown shawl cardigan, dress shirt, tie, dress pants, and loafers outfit

This beautiful brown shawl cardigan over a light blue chambray button-down shirt is perfect for a spring day out.

The blue pants and brown shoes really give a kick to this ensemble.

Don’t forget about the accessories if you want to dress up your look.

Add a navy paisley tie for a touch of texture and dark brown sunglasses for an elegant finishing touch.

Small Detail but Counts

Brown sweater, patterned dress shirt, gray trousers, and brown loafers outfit

The camel-toned sweater provides a warm contrast to the cool, dark hue of the slim-fitting trousers.

Layered over a patterned dress shirt, the look is both polished and approachable.

This is complemented by a navy dotted scarf neatly tucked into the dress shirt.

Burgundy V-Neck Sweater

Burgundy v-neck sweater, light blue striped dress shirt, charcoal chinos, and dark brown sneakers outfit

The deep burgundy of the V-neck sweater envelops the crispness of the light blue striped dress shirt.

Below, the charcoal chinos offer a sleek yet comfortable base.

Grounding the look, the dark brown sneakers infuse an element of contemporary cool, challenging the traditional dress shoe norm.

Green Cargo Pants

Cream sweater, white dress shirt, green cargo pants, and brown chukka boots outfit

This ensemble strikes a confident note with its earthy green cargo pants, making a bold statement without saying a word.

Topped with a cream sweater that whispers sophistication, and a crisp white dress shirt peering from underneath, it’s a classic with a twist.

The brown chukka boots are the perfect punctuation.

With a Dark Green Suit

Dark green suit, navy cardigan, dress shirt, and monks outfit

The stylish chaps frequently choose this refined outfit with a dark green suit and a blue cardigan.

This outfit is brought together by a nice pair of brown leather double monks.

So untuck the top two buttons of your dress shirt and skip the tie for a dapper look!

Wear Striped Button-Up Dress Shirt

Polo neck sweater, dress shirt, dress pants, and loafers outfit

A dress shirt with light blue vertical stripes and a wool polo neck solid sweater?

This business casual ensemble is great for work.

To complete this get-go, try wearing charcoal pants and brown shoes such as suede loafers.

Cashmere Cable Knit Sweater

Beige cable knit sweater over a dress shirt, beige trousers, and black lace up boots outfit

Few things are as versatile and comfortable as a cable sweater.

Whether you dress it up or down, this cozy sweater is always a great option for fall outfits.

Beige trousers and black lace-up boots beautifully anchor the whole getup.

Wear Black Overcoat

Black overcoat, cable sweater, white dress shirt, and leather oxfords outfit

Wear a sweater over dress shirt combo for this black overcoat outfit.

Make sure that your accessories complement the overall look.

Black print tie and black leather Oxfords look immaculately stylish.

Black Parka

Wearing a black parka, tan cable sweater, dress shirt, and casual boots

Parka jackets are stylish pieces perfect for cold weather.

If cold weather strikes, just pull out a tan sweater over a dress shirt.

Additionally, wear blue denim jeans and brown leather boots.

Finally, please don’t skip the black tie, as it will give formality to your look.

Or a Navy Parka

Navy wool parka, cable sweater, dress shirt, and boots outfit

A navy wool parka can add an edge to this neatly put-together winter outfit.

Add navy vertical striped dress pants and a pair of dark brown lace-up boots.

Beige Duffle Coat

Duffle coat, cable sweater, dress shirt, and brown shoes outfit

A traditional duffle coat is made of a cozy wool blend and intended to keep you warm.

You may add some casual elegance to your everyday uniform by wearing a beige duffel coat with black pants.

Brown leather loafers would be a more traditional choice for footwear.

Wearing Sweater Over Dress Shirt Outfits: The Basics

This effortless style will complement any outfit, regardless of the time of year.

Let’s explain some fundamentals before you start layering your look.

Choose a Proper Dress Shirt

A properly fitted dress shirt will make all the difference.

A good rule of thumb is to buy a size that fits comfortably around your waist, sleeves, and shoulders.

Choosing a proper dress shirt size and style

You’ll have to deal with unpleasant bunching under your sweater if it’s too big.

It would be best to aim for breathable material with lighter dress shirt fabrics such as 100% cotton, broadcloth, or poplin.

Also, you don’t want to wear your dress shirt untucked if it is longer than your sweater.

And lastly, your dress shirt collar tips should also be tucked in.

Different Types of Sweaters

When layering a sweater over a dress shirt, it’s important to understand the variety of sweaters available and how they can complement your style:

Different types of sweaters to wear over a dress shirt
  • Crew Neck: The classic cut. It sits around the base of the neck and works well with most body types. Ideal for a clean, academic look.
  • V-Neck: Offers more depth and is perfect for showcasing the dress shirt underneath. It’s a good choice if you plan to wear a tie.
  • Cable Knit: Textured and thick, adding a cozy feel. Best suited for casual settings or cold weather due to its bulkier nature.
  • Cardigan: A button-up or open-front sweater. It’s versatile and can be dressed up or down. Plus, it’s easy to put on and take off as needed.
  • Turtleneck: Provides a sleek look while keeping your neck warm. It can replace the need for a scarf and gives off a sophisticated vibe.
  • Sweater Vest: Sleeveless and excellent for a preppy aesthetic. It layers well without adding bulk to the arms, keeping the silhouette streamlined.
  • Quarter-Zip: Sporty and functional. It can be zipped up to different heights depending on the desired exposure of the dress shirt.
  • Cashmere: Luxurious and soft. While not a style per se, the material choice is crucial for comfort and exudes a sense of luxury.

Each type serves a different aesthetic and functional purpose, so consider the occasion, weather, and your personal style when choosing the right sweater to layer over a dress shirt.

Matching Colors and Patterns

Consider wearing neutral shades for a more conservative look appropriate for the workplace.

Matching colors and patterns between a sweater and a dress shirt

That includes brown, navy, white, khaki, gray, and black.

Wearing the same shade in multiple items is a big mistake.

It will look monotonous.

Try pairing a solid-colored shirt with a patterned sweater or vice versa.

Another option is to wear a dress shirt of solid colors and a sweater with a patterned tie.

On the other end, mixing patterns can be a bit riskier.

You can go for stripes or checks, but make sure they are subtle and fit the outfit well.

We recommend if you choose to go for patterns, go for only one item.

Christian Barker
Christian Barker

Christian Barker, a prominent voice in the fashion industry, started in music promotion before finding his calling in media. He's held significant roles in Australia, the UK, and Singapore. As the founding editor of The Rake magazine and August Man, Barker left an indelible mark on men's style. Today, he shares his expertise on fashion in renowned outlets like Asia Tatler and Forbes Asia. In Singapore since 2005, Barker is passionate about unique experiences, authentic luxury, and timeless tailoring. His keen eye for style and dedication to sustainable luxury truly sets him apart.

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