How to Style a Dress Shirt for Any Occasion

Like most people, you probably own at least three dress shirts. But if someone asked you to explain the difference between them, you might be hard-pressed to get past, “Well, this one’s blue.”

That’s okay—it means you’ve been buying what looks good without overthinking it. But knowing which types of dress shirts work best for various occasions can turn getting dressed from a guessing game into a styling choice that clicks every time.

Understanding the subtle differences between dress shirt types and styling can give you more options. And once you know what you’re looking for, you can learn how to style a dress shirt up or down for any occasion.

In this guide, we’ll break down types of dress shirts, styling tricks, and how to wear a dress shirt for every single occasion.

What Is a Dress Shirt?

At its core, a dress shirt is a collared, button-front woven shirt built with precision in mind. The collar stands tall, the buttons line up evenly, and the fabric holds its shape through whatever your day throws at it.

Woven fabrics set dress shirts apart from casual button-downs, giving them structure and durability. Meanwhile, collar styles range from spread to point to button-down, and each choice shifts how formal the shirt wears. Traditionally, dress shirts are woven. With modern technology, knit dress shirts have become more prevalent, often mimicking the look of a woven shirt but providing extra stretch and a softer hand feel.

The dress shirt we know today traces back to the 19th century, when men stopped wearing cravats and started buttoning their collars. What began as a formal undergarment for the upper class in the 17th century eventually became an everyday essential. Fast forward to today, and they’ve evolved into versatile wardrobe staples you can wear a dozen different ways. Collars and cuffs were originally detachable for laundering and cheaper and easier replacement.

Men’s dress shirts typically get tucked into trousers or tailored pants, creating the refined silhouette we all know and love. But the definition has loosened over time, turning a once-rigid style into a versatile fashion choice.

Now, you can wear dress shirts untucked, layered, or even over a tee. This adaptability is what makes owning more than one worth it.

Types of Dress Shirts

Not all dress shirts serve the same purpose, and that's a good thing. The fabric, collar, and overall construction determine whether a shirt works best for a suit or pairs better with jeans.

Here's how to tell them apart.

Formal Dress Shirts

Formal dress shirts use smooth fabrics designed to hold their shape under a suit jacket. High threat counts, structured collars, and stiff fabrics keep them looking pristine for hours.

You’ll want to reach for a formal dress shirt during these occasions:

• Weddings or black tie events
• Interviews, board meetings, and client presentations
• Anytime you’re wearing a full suit and tie

Formal shirts typically come in white, light blue, and other neutral tones. Patterns are often subtle, like thin stripes or micro checks that appear solid from a distance.

All of these stylistic choices help convey sophistication without competing for attention.

Business-Casual Dress Shirts

Business casual shirts balance professional refinement with approachable comfort, making them more appropriate for semi-formal occasions. The fabrics breathe better, move more easily, and don’t demand the same level of formality as formal shirts.

These work best when you're:

• Heading to the office but leaving the tie at home
• Pairing with blazers, chinos, or tailored trousers
• Going to an event with a more relaxed dress code

You’ll find more texture and color options with business casual shirts. The collars might have a slight roll instead of a stiff edge, and the overall vibe is put-together without feeling uptight.

Casual-Friendly Dress Shirts

These shirts blur the line between dressy and laid-back. Textured fabrics like linen blends, lightweight flannels, and chambray give them character and help them breathe more easily. The collars can be button-down, and the fit might run slightly relaxed.

The sport shirt, originally intended for use playing sports like golf, polo, and tennis, but in modern times has blurred the lines between a dress and sport shirt. The button down collar, bolder prints/deeper colors, and chest pocket are all classic hallmarks of a sports shirt that have been incorporated into more casual shirts to this day.

These shirts are perfect for:

• Weekend plans where you want to feel stylish, but don’t need a rigid structure
• Pairing with jeans or casual chinos
• Layering under casual jackets or wearing solo with the sleeves rolled up

Casual dress shirts open up your wardrobe. They're the ones you grab when you want to look put-together without looking like you’re on the way to a meeting.

Patterns and colors are also bolder with casual-friendly dress shirts, offering plaids, stripes, flannel, and other printed fabrics.

How to Style a Dress Shirt Casually

The best part about styling dress shirts casually is that they clean up any outfit without making you look too overdressed. Here’s how to pull it off.

Pair With Jeans or Chinos

Dress shirts and denim are old friends. The classic combination works because the shirt brings structure to the jeans' easygoing attitude. Choose darker washes for a cleaner look or go lighter if you're channeling weekend energy.

Chinos split the difference between jeans and dress pants. Navy, olive, or khaki chinos with a crisp white or chambray dress shirt is the uniform of someone who has his act together without needing to announce it. You can even opt for the Mayfield Pant as an alternative to denim.

To pair your dress shirt casually with any pants style, roll the sleeves to the elbow. This small move makes your dress shirt look more relaxed and can help show off accessories around your wrist or give your outfit some visual breathing room.

Wear Untucked or Half-Tucked

Tucking isn't always necessary. If the hem hits right at your hip bone and doesn't drape past it, wearing the shirt untucked can work well. Just be sure to focus on proportion. If your tuck is too long, it looks sloppy. Get it just right, and you look intentionally disheveled.

Half-tucking adds a casual edge while keeping the look balanced. Tuck just the front center of the shirt into your pants, letting the sides hang loose. This styling feels effortless once you nail the placement.

Remember to check the hem before committing to the untucked look. Shirts designed to be worn untucked have straighter, shorter cuts that won’t bunch up.

Add Lightweight Layers

If you want to change the vibe of your entire outfit, play with layers. A crew neck tee underneath your dress shirt creates a relaxed, textured look. You can even leave a few buttons open and let the tee peek through at the collar. Throw a casual jacket or flannel over your dress shirt, and you add depth without much more effort.

Texture also matters. For example, a crisp dress shirt under a textured jacket creates dimension in your outfit. The contrasting textures keep things visually appealing.

How to Style Dress Shirts for Formal Occasions

When the occasion calls for formality, it’s important to get the details right so that everything else falls into place.

With a Suit and Tie

A suit, tie, and dress shirt form the classic foundation of formal menswear. Keep the shirt in a classic muted color and let the tie introduce your personality.

Fit is also essential. A well-fitting dress shirt should lie flat across the chest and shoulders without pulling. Sleeves should peek out just past the jacket cuff, showing about half an inch of fabric.

For styling with a suit and tie, you also want to pay attention to shirt collar vs jacket lapel vs tie width proportions. Traditionally, you want all three to be the same width. You have the creative freedom to break from tradition, but be sure none of these is significantly wider or smaller than the others for a classic look.

Finally, consider your collar style and choose one that matches your tie knot. Spread collars handle larger knots well, while point collars work best with slimmer ties.

With a Blazer and Trousers

A blazer and trousers with a dress shirt still looks professional, but doesn’t shout “board meeting.”

Trust this combination to carry you through client dinners that don't require full formality, business travel when you need to look ready the second you step off the plane, and semi-formal events where you're expected to dress well but a full suit would be overkill.

Add Dress Accessories

Cufflinks, pocket squares, and tie bars are details that separate a good formal look from a great one. They're small, but mighty signals that you care about the finish.

When it comes to footwear, opt for dress shoes in black or brown, depending on the formality level of the event and your overall color palette. A leather belt that matches your shoes will tie the whole look together.

Above all, don’t overthink your accessories. One or two pieces are plenty to make the outfit look intentional.

Additional Dress Shirt Styling Tips

Beyond the basics, there are a few details that separate guys who just wear dress shirts from guys who actually style them.

Choose the Right Fabric

The fabric you choose has a massive impact on how formal or casual a dress shirt feels.

• Smooth, tightly woven fabrics like poplin or broadcloth signal formality loud and clear. They hold their shape, resist wrinkles better, and look pristine under a jacket.
• Textured fabrics like Oxford, chambray, and linen blends are more casual. They breathe better, feel softer, and don’t demand the same level of fussing and care.

Performance fabrics take things a step further by offering the same classic look of a dress shirt with added benefits like breathability, wrinkle resistance, moisture wicking, and more. Since dress shirts are often known for being stuffy, performance fabrics can help you look forward to long days wearing your dress shirts rather than leave you obsessively checking the weather forecast.

Focus on Fit

A properly fitted dress shirt can make or break your look because it's the foundation everything else builds on. When the fit is right, you stop thinking about what you’re wearing and start focusing on what you’re doing.

Here are the components of a well-fitted dress shirt:

• Shoulder seams hit right at the edge of your shoulders, rather than drooping.
• Fabric falls across the chest comfortably without excess bunching.
• The cuff hits right at the wrist bone, sitting just past where the hand meets the arm.
• The back hem is slightly longer than the front to account for tucking. Or, for untucked shirts, the cut hits right at the hip.

Use Color and Pattern Thoughtfully

Solid colors are the easiest to work with. White, light blue, and other neutral tones pair with everything and transition easily from casual to formal. Start building your collection around these, then add patterns and bolder colors as accents.

Keep in mind that patterns can make any outfit slightly less formal. Thin stripes will still work in professional settings, but plaids, checks, and bolder prints lean more casual. Use them to add personality to your outfit while still having the classic look of a dress shirt style.

When mixing patterns, vary the scale. For instance, a subtle striped shirt under a plaid blazer can work if the stripes are thin and the plaid is larger. Basically, the patterns shouldn’t compete for attention; one should take the lead while the other supports it.

Additional Tips

Lead with fit. In menswear, fit is most important, and if the fit is off, the look is instantly less impactful. When buying, focus on fit first, and know what can be tweaked by a good tailor if needed. Focus on a fit that matches your body type, style, and comfort.

When mixing patterns, pick 2 items and leave the third solid. For example, a larger pattern suit, a smaller pattern dress shirt, and a solid tie. Also vary the depth of color to increase contrast and create a memorable look.

Style Your Dress Shirts with Mizzen + Main

When it comes down to it, you can wear a dress shirt for just about any occasion—if you know how to style it right. Knowing how to style a dress shirt and having a variety of well-fitted options to work with makes it easy to put together outfits with confidence.

If you’re ready to start incorporating more dress shirts into your wardrobe, choose Mizzen+Main shirts that combine classic style with performance features like breathability, moisture-wicking, and 4-way stretch. You’ll look good and feel good without compromise. Explore our collection today.

Sources:

Encyclopedia.com. Dress Shirt.(opens in new window)