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How to Style a Men’s Dress Shirt (for Men and Women)

The men’s dress shirt is such a ubiquitous item, it’s easy to forget about it. But then, you want to wear one. And you realize that you’re not sure how to style it, what kind of dress shirt you should wear, when it’s going to look good and how to accessorize it to put together a good-looking style. It all seems so simple until you find out how many different styles of dress shirts there are and how many different ways you can wear all of them. Learn all the tricks for how to style a mens dress shirt and you’ll learn how to put together a lot of amazing looks for all sorts of different occasions. 

Man wearing white dress shirt

 History of the Dress Shirt

 Dress shirts are such an integral part of fashion today, it’s hard to imagine a time without them. To do that, you’d have to go back about 400 years. Dress shirts have been a part of wardrobes since the 1600s. However, they were more like undershirts. In their early designs, men’s dress shirts were meant to be worn under frock coats and waistcoats (vests). It wasn’t until the 1800s that shirts truly became a distinct part of the outfit. Now, they were made to be seen.

 The basic style of dress shirt has hardly changed since those Victorian Era days of the 1800s. Today, dress shirts are a staple of many male wardrobes and a fun style choice for women, too. There are many ways to style a men’s dress shirt for those who like clothing styles of either gender.

 Dress Shirt Styles

Men’s dress shirts sort of all look the same. They’re all collared, long-sleeved, button-up shirts. However, there are many, many different types of dress shirt styles within this basic framework. You can go way beyond a basic black dress shirt or a crisp white shirt. There are a lot of ways to play with dress shirt style.

Blue dress shirt casual look

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 Different Types of Dress Shirt Fits

 Dress shirts are made with many different types of fit that affect the way you look and feel. Which type of fit is best suited to your body shape? Take a look at the characteristics of different types of dress shirt fits and you’ll find it much easier to pick out the right dress shirt for you.

  •  Classic

The classic fit shirt is one of the most popular and it’s a standard size that you can usually find anywhere that dress shirts are sold. The classic fit is somewhat loose around the arms and body and has a boxy shape. This is a comfortable shirt, which is why this fit is considered classic. The waist of the shirt is relaxed and the armholes are roomy. This shirt offers plenty of moving room so it fits men with larger and average frames quite well. Slender frames, however, may find this fit to be too loose and roomy.

  •  Modern

The modern fit has a slightly more tapered fit than the classic style but it is still somewhat roomy around the body to keep it comfortable. The waist is slightly tapered, the sleeves have a full fit and the armholes are relaxed.

  • Skinny

The skinny fit dress shirt is designed to fit close to the chest and shoulders. It also has tapered sleeves and a slim, tapering waist. This fit really only works on slender body types because it is made with a narrow, slim cut that’s designed to sit close to the body. However, it’s not meant to restrict movement. This shirt fits well on narrower frames, staying close to the body without causing discomfort.

  • Slim

The slim fit dress shirt design is a very popular style. This creates a tailored, tapered look. The sleeves are tapered and the waist has a slim fit. The chest has a slim fit as well and the armholes are high. This gives the shirt a sleek fit that works well on athletic and slim body types. The slim fit shirt looks very good even without a jacket, as it does not billow out or bunch up anywhere. Slim fit dress shirts fit close to the torso all over without a lot of bagginess or any excess fabric.

Get the Looks

You’ll find lots of different men’s clothing styles at Mango, which also offers a big selection of dress shirts. The clothing here looks high fashion but doesn’t cost like high fashion. The clothes here are well-made ad designed in all the latest, trendy styles. If you like to stay up-to-date on your fashion, this is the perfect place to shop.

Dress Shirt Collars

Though dress shirts have the same basic features, those features are not always the same. This is certainly true with dress shirt collars, which are designed in many different styles. Each of these has its own distinct look. 

  • Band

This is perhaps the most casual of all collar styles. Unlike other designs, this is a simple band with no fold and no collar points. It’s about three centimeters high and usually has a simple, single button closure. 

  •  Club

The club collar is one of the most distinct styles. Originally made for school uniforms, this collar has rounded ends, rather than points. It also has a wide spread with sharp angles.

  •  Cutaway

The cutaway collar is a short collar compared to other styles. It has wide ends, which are sharply angled and spaced wide apart from each other. Because of the wide collar spread and the shorter length, this shirt collar is not ideally suited o wearing a tie. However, it looks great for more casual dress shirt styles. When you want a collared shirt to stick up out of another shirt, this is a great choice.

  • Long Button Down

The long button down collar is a casual style with buttons on each point of the collar. The gap between points is medium-wide. The collar is long and will sit up on the neck to provide plenty of room for a tie. 

  •  Semi Spread

The semi spread collar has pointed ends that are just a bit elongated. The collar is spaced so that there is a large gap between these two points, which are angled to point toward the shoulders. This style is well-suited to longer necks, as the spread collar design helps break up the collar at the throat so it doesn’t make the neck look too elongated.

  •  Short Button Down

The short button down collar also has buttons on each collar point, like the long button down variation. However, this collar is somewhat shorter and does not sit up on the neck quite as high as the long version. 

  •  Spread

The spread collar is a popular collar style that has a uniform length that isn’t shortened or elongated anywhere, with standard points that angle away from each other over the throat. This is a casual look because the spread collar is so wide, which means it looks best without a tie. 

  •  Straight Point

The straight point collar has an elongated length. This can create a slimming effect on the neck and face. 

  •  Wingtip

When you see a wingtip collar, you know it. This collar has just two small points, folded downward, to create a highly formal look. That’s why this style is also known as tuxedo style. The collar was designed specifically to be worn with a bow tie but is also worn with regular neckties and ascots. When you need an eye-catching formal shirt that will turn heads, a wingtip collar will do quite nicely.

 Get the Looks

Jos.A.Bank is a famous name in men’s fashion. This storefront has a big selection of dress shirts in different colors and styles. Here, you can search by fit, look for vintage styles, look for shirts by color or pattern or even shop by collar style. Shirts here are available at affordable prices and some items here go on sale periodically, so you can wait for a good deal to come along. 

 Extras

Dress shirts have a basic style that is modified thanks to collars and the fit design. But there are other little extras that can make a shirt more distinctive, or perhaps distract from the style you’re trying to create. It’s up to you to decide whether the embellishments swill enhance or take away from your overall look. 

  •  Buttons

The buttons on dress shirts are usually made with plastic. In some designs, the buttons may be mother-of-peal. Buttons can be clear or white in many standard designs, or they can be made to match the color of the shirt. Sometimes, buttons are dyed to contrast against the shirt to add a pop of color to the design. 

  •  Monogram

Some dress shirts may be embellished with an embroidered monogram, the initials of the owner of the shirt. The monogram may be very noticeable, placed on the chest somewhere, or very discreetly placed on the collar.

  •  Pocket

Some dress shirts have pockets on the left side of the chest. This pocket is rarely ever used but it adds a little extra to the shirt.

Get the Looks

Charles Tyrwhitt is a beloved name in British fashion. Through the magic of online storefronts, anyone can shop for dress shirts bearing his label. There is a huge selection of dress shirts here, including styles in multiple colors and collar styles. Find shirts in solid and patterned designs made in a number of different fabrics.

 Styles for Men to Wear

Once you’ve found the right types of fits and collar styles for your dress shirt, once you’ve picked some designs that bear a few extras, you’re ready to start wearing dress shirts. But…how? There are many different ways to style men’s dress shirts to create exactly the look you want and put off just the right vibe for whatever situation you’re in. Learn how to style a men’s dress shirt like a pro to pull off all sorts of looks and you will literally be ready for any event. 

Casual

Amazon Essentials Men's Regular-Fit Long-Sleeve Solid Oxford Shirt, White, XX-Large

Leave the dress shirt untucked and undo the top button or the top two buttons. Now, slip into a pair of jeans. Finish it with sneakers and roll up your sleeves. This creates a great casual look that can go anywhere. This is a great look for running errands, hanging out with friends or going on a casual date. Wear darker shades of jeans and dress shirts for evening and night events and lighter-colored shirts and shoes for the daytime.

Professional

Calvin Klein Men's Slim Fit Suit Separates, Solid Navy, 40 Regular

Look professional and polished by wearing a dress shirt with a suit. Add a matching tie and pocket square to give the look a pop of color. Black or brown dress shoes, such as oxfords, with a matching belt will finish the outfit. This will give you a conservative and professional style that is suitable for all office environments, professional business lunches and meetings and other business occasions.

One tip to follow is to pair a solid dress shirt with a patterned suit, such as a pinstripe. Pair a patterned dress shirt with a solid suit. This will give your look depth. Stick to very small, discreet patterns for conservative professional environments. 

  • Casual Professional

A variation on the style is to lose the tie and leave the top button of your dress shirt undone. This style is somewhat less professional because it adds a touch of a business casual vibe. However, this can be a powerful look, as it says you’re confident and relaxed even in tense business situations. 

  • Formal Professional

If you want to take your look up a notch, add a vest. This will add one more layer to your look and help you create that really polished, very professional vibe. 

Preppy

Cashmeren Men's Classic Knit Sleeveless Sweater Vest 100% Pure Cashmere V-Neck Pullover Gilet (Mocha, Medium)

Capture a classic preppy style with a mens dress shirt by pairing it with a sweater vest and tie. This look is very preppy and great for semi-casual events of all types. Wear it with dress slacks for more semi-formal occasions and with khakis for more casual events. A pair of loafers with a matching belt will finish this look off nicely. 

Sexy Casual

COOFANDY Men's Western Casual Shirt Button Up Basic Solid Linen Business Shirts

Open the top two buttons of your dress shirt and add a pair of fitted slacks. Tuck the shirt in and forget about wearing a belt. Finish off this sexy casual look with a pair of loafers. This look is sort of that of the professional who is now unwinding and being relaxed, but he’s still a professional man so he’s still well-dressed. It’s a very elegant look for casual events and being at home. This is a great date look if you’re hosting them at your home. 

Smart Casual

Van Heusen Men's Poplin Regular Fit Solid Point Collar Dress Shirt, White, 16.5" Neck 34"-35" Sleeve

Capture a great smart casual look by wearing a V-neck sweater over your dress shirt. To look more casual, unbutton the top button of the dress shirt. To look a little less casual, wear a tie under the sweater. Wear this with dark slacks for evening events and khakis for daytime events. Either way, you’re going to look put together and casual without being too casual or underdressed. 

Get the Looks

Find a beautiful selection of men’s shirts at Cubavera. Their shirts are available in a big range of different colors and they’re made with linen, a durable natural fabric that hangs well and looks expensive. 

Styles for Women to Wear

If you’re creative, you can probably find lots of ways to wear a men’s dress shirt that will look good and be stylish. You can find ways to wear it just as it is, playing around with the button and collar configuration. You can find different ways to tie it so that it no longer even looks like a men’s dress shirt. Experiment with different ways to style a men’s dress shirt and have some fun with his common wardrobe staple.

Backless Shirt

WARHORSEE Womens Button Down Shirt Long Sleeve Work Dress Shirts, V Neck Easy Care Stretchy Business Casual Blouses for Women(White,XL)

Button the shirt all the way up. Fold the top of the shirt down behind the buttons and then place it across your chest so that the buttons line up with the middle of your body. Tie the sleeves together on your back, then bring them forward and tie them together just under your bustline. This will create a backless, cute shirt that emphasizes the bust and provides a little camouflage for the tummy. 

High Fashion

Alex Vando Womens Dress Shirts Regular Fit Long Sleeve Stretch Work Shirt,Black,M

Create a high fashion look with a men’s dress shirt by first selecting a good-looking shirt. If it’s got a contrasting collar, a great pinstripe pattern or French cuff, even better. Either way, wear it with two to three of the top buttons undone and half-tucked into a stylish pair of pants that fit well. Fitted slacks or skinny jeans will look good against the somewhat blousy, loose fit of the shirt. 

Add some amazing shoes, like ballet flats or heels, and a pair of dark sunglasses. You will look incredibly chic and it will look like you spent a lot on your style. You can also achieve a high fashion look by dressing all in black, such as wearing a black shirt with black pants, and adding a single pop of color by using an accessory as a focal point.

Low and Open

jonivey Womens Button Down Long Sleeve Regular Fit V Neck Stretch Work Shirt (White,S)

Create a great casual look that’s just a little bit sexy, too, by wearing a white men’s dress shirt with jeans. Unbutton the top two buttons, leave two buttons done and then undo the rest to create a low, long opening at the bottom of the shirt. This will playfully show some skin and show off your waist and stomach at times, offering little glimpses that can be super sexy. 

Make Your Own Dress

Shirt Dresses for Women Button Down Sexy Loose Newspaper Floral Print Top Long Sleeve Collar Blouses White

Of course, the men’s dress shirt very easily creates one look that has become pretty classic: the shirt dress. Use a belt or a scarf to turn a men’s dress shirt into a short mini dress that bares a lot of leg. Unbutton the shirt at the top to show a little cleavage and you’ve got a great look that’s super sexy. 

Strapless Dress

Design by Olivia Women's Classic Long/Roll Up Sleeve Button Down Denim Chambray Shirt Light Denim L

There’s a specific way you can tie a men’s dress shirt to create a very cute strapless dress. First, wrap the top of the shirt around your body. The buttons should go on the center front, as usual. Take the sleeves in either hand, twist them, and bring them around to your back. Here, they can be crisscrossed and brought back around to the front. Take the sleeves around to the waist and te the here to create a super cute summer look. 

Tied Up

GRACE KARIN Women's Plus Size Button Down Shirts Long Sleeve Blouse Wear to Work Formal V Neck White XXL

Take the dress shirt and unbutton the collar and the button under it, then unbutton the last two buttons at the bottom. Depending on how the shirt is made, you may need to undo an extra button up top or on bottom or both. From here, take each end of the shirt in your hands and roll the back of the shirt up to above the small of your back. Take the two ends and bring them in front, cross them and tie them together. You can tuck the knot through the shirt if it’s bunched up in front. 

Tuck and arrange the style until you’ve got a waist-defining tucked up look. This look adds volume around the bust area and frames your neck and face with the collar but it also defines your waist to make you look thinner. It looks like a casual, effortless look when really, you’re showing off your assets to their very best effect. 

Tuck It In

GRAPENT Women's Casual Collared Rolled up Long Sleeve Loose Blouses Pockets Button Down Shirt Tunic Top Brilliant White Size Large Size 12 Size 14

Create a stylish, preppy look by tucking a mens shirt into high-waisted dress pants or shorts. Roll up the sleeves to shorten them and give yourself a look that says you’re beach ready but still glam. The high waist provides definition for your waist and hips, while the more blousy shirt will help make your bustline appear a bit larger.

Under Something Else

MKolour Womens Button Down Shirts - Long Sleeve Work Dress Business Office Button Up Blouse Collared Shirt White, Medium

You can always wear a dress shirt under a dress or a shirt to add sleeves and a collar to anything you want to wear. This can be a very easy way to convert a summer top or dress into something more fall- or winter-friendly. 

Get the Looks

Ralph Lauren is one of the top designers in men’s fashion. The Ralph Lauren storefront is full of men’s dress shirt styles in a variety of colors. Many of the shirts here are available in different fits, so you can pick a style and then select the fit you need. 

FAQs

There may be a lot you still don’t know about wearing dress shirts. We’ve got the answers to all the most common questions about men’s dress shirts. When you have the answers, you’ll always know how to create great style. 

White dress shirt stylish outfit

What do men’s dress shirt sizes mean?

Dress shirts come with different styles of collars and cuffs, even different styles of pleats. They have different types of fit. But in spite of all this, your size is always the same because you will always base your dress shirt size off of your measurements. 

The measurements you need are your neck, sleeve, chest and waist. To accurately get these measurements, wrap a flexible tape measure around your chest at the widest point. This is usually under the shoulders near the nipples. Measure around your neck near the base of your neck, where you will wear the collar. The waist should be measured around the thinnest part, rather than the thickest, usually near the belly button. The sleeve is measured from the top of the shoulder to the base of the hand. 

Once you have these measurements, always compare these against size charts when buying a dress shirt. Our size charts show the standard sizes but some manufacturers may use their own variations. When you have your measurements, you will always be able to find your size.

What men’s dress shirts will look good on you?

Choose your dress shirts based on the way they fit and on the color. You want to wear a dress shirt in a shade that will complement your natural shading. 

Do you have pale skin? If so, wear a high contrast dress shirt in a rich color shade. This will help brighten your face, rather than drowning it out. Bold shades of red, warm purple, green and blue will be the best dress shirts for you.

If you have more medium color, such as tan or brown skin and darker hair, try more neutral color tones like olive green, mustard yellow, pale brick red and brown. Gold and copper shades will work well on you, too.

A more low contrast natural coloring, such as pale skin and pale hair, will look best in paler colors. Try pastels, off-white and other soft colors. Gray, pastel blue and white dress shirt styles will work for you

If you have dark skin and dark hair, look for cool color shades in vibrant shades of turquoise, purple and blue. Bright weight and light gray also work very well. 

Look for the right shirt fit, too. If you have a more slender body type, try a more slim-fitting style. If your size is average to somewhat muscular, a classic style will work well for you. Try on different types of fit and start with this. Once you have the right shirt cut, you can start to play with wearing different colors and different dress shirt collar types.

Why do men’s dress shirts have pockets?

Men’s suits have breast pockets, where a pocket square is often stored to add a bit of color to the outfit. This pocket was born out of necessity, as it used to be common practice for men to carry handkerchiefs with them. In the days before disposable tissues, this was a necessity. But why do dress shirts have pockets when suits and blazers already have this pocket? 

The dress shirt pocket is used to add style and convenience to shirts. The shirt pocket is a handy place to keep handkerchiefs and other small items when you are not wearing a jacket. In hot weather climates, you might wear a dress shirt with no jacket. 

The dress shirt pocket once saved the life of a President. In 1912, a would-be assassin shot Theodore Roosevelt right in the chest as the President was leaving a rally. Instead of lodging in Teddy’s lung, the bullet struck the folded pages of a speech that he was carrying in his breast pocket. The speech was a whopping 50 pages, thick enough to absorb and stop the bullet. For the record, Roosevelt gave the entire speech before he sought the aid of a doctor to have the bullet removed. It had lodged in his ribcage. There have been other cases of an item in a breast pocket saving a life, so perhaps the dress shirt pocket is far more valuable than it first appears!

How does fabric type affect dress shirt fashion?

Dress shirts are made from all different types of fabrics. The fabric you wear absolutely affects how the shirt looks. Fabrics have different weights and they drape differently. They also play a big role in your comfort, which is something you can’t overlook.

Cotton is an extremely common shirt material. However, it’s usually made with a specific weave that gives it certain qualities. Oxford is a durable shirt material that’s comfortable but slightly rough in texture. It’s used most often in more casual shirts. 

Poplin is another type of cotton fabric that’s used for men’s dress shirts. Popline is a somewhat fine, lightweight weave that is used in more casual shirt styles. Twill is a blend that usually contains cotton and another type of fabric, such as polyester. Twill can be made in many different thicknesses and has lots of different properties, as any two fabrics blended together into one design is a twill. 

Broadcloth is very much a standard in shirt making. This material is a lightweight cotton weave that has a fine texture. The material is highly durable and has a nice look to it. Broadcloth is used to create more professional or semi-formal wear. The tight weave gives the shirt a very fine finish. This also means the shirt hangs well on the body. 

Silk, more expensive than cotton, is another common dress shirt material. Silk is incredibly soft and non-irritating on skin. It has a somewhat clingy natural drape, so silk works well in shirts that fit close to the body.

What should you look for in the best men’s dress shirts?

There are so many different options out there, it can be a little overwhelming to shop for dress shirts. How should you choose what’s right for you? Once you have a handle on finding the right fit, the right collar style and the colors that will work well for you, what else should look for in a good dress shirt? 

Take a look at the extra features, such as double stitches, reinforced buttons and bartacking that show a more durable design. Features like machine-washability and wrinkle-resistance are a big plus as well. Look at fabric composition to get an idea of the quality of a shirt. Natural materials, such as cotton and linen and silk, feel good on skin and wear well. Synthetics, such as polyester and rayon, are more affordable but you may sacrifice quality as a result. 

How should men’s dress shirts fit?

Dress shirts must fit perfectly. Otherwise, you’re going to be uncomfortable. The collar of the shirt should sit around your neck with no visible gaps but it should not choke you or restrict your throat. You should have no trouble talking and swallowing while wearing your dress shirt buttoned all the way up. You also want the seams on the shoulders to line up with the top of your own shoulders. 

As for the chest and the waist, the fit should not be tight enough to restrict your movements and should not be so loose that it bunches up and gets twisted while you’re wearing the shirt. The cuffs should end at the base of your hands, with cuffs that fit around the wrists with no visible gaps. Again, the cuffs should not be tight enough to restrict your movements or dig into your skin. 

How do you iron a men’s dress shirt?

A wrinkled dress shirt is always going to look bad. To truly master the art of wearing a men’s dress shirt, you’ve got to know exactly how to iron it. Start with a damp shirt. If the shirt isn’t already damp, use a spray bottle to moisten it slightly. 

Look at the label on the shirt. You should see a little iron symbol with dots. The dots tell you how high or low the temperature of the iron should be so that you can iron the shirt. 

Start by ironing the collar, which should be lying flat on the ironing board. Tug the collar straight and flat with one hand while using the other to guide the iron over the material. Iron it this way on both sides. Do the cuffs next, following the same technique.

The sleeves are the hardest. Take your time placing the sleeve on the ironing board and smoothing it out. Make sure both sides of the sleeve are smooth and flat or you’ll have a devil of a time ironing out the wrinkles later. When it’s all flat, iron from the middle out. Flip the shirt and do this on both sides of the sleeve, then repeat the whole process with the other sleeve.

Do the shoulder area next. This can be tricky because you’ll want to fit the shirt over the end of the ironing board. Starting on one side, iron and move the shirt. Iron and move and iron and move until the shoulder area is free of wrinkles. 

Lastly, iron the front and ack of the main body of the shirt. Now, you’ll look amazing!

Sources:

All Day Chic – 10 Ways To Wear A Men’s Shirt

Blitz Results – Dress shirt size charts: THIS is how you find your perfect fit

Byrdie – 11 Ways to Spruce Up a Simple Button-Down Shirt

Gentleman’s Gazette – Men’s Dress Shirt Style Guide – How to Select Fit, Collar, Cuffs & Details

Love to Know – Dress Shirt

OverUnder Clothing – Why Men’s Breast Pockets Exist: A Brief History

Real Men Real Style – 10 Tips To Look Attractive In A Dress Shirt

Real Men Real Style – Dress Shirt Fabrics Every Man Should Know | Men’s Shirting Guide

Suits Expert – Men’s Dress Shirt Guide: Styles & Types

WikiHow – How to Wear a Dress Shirt