How to Choose the Right Men's Dress Shirt
In this day and age, it’s easy to get lost in the abundance of choices—but we’re here to help. This men’s dress shirt guide will answer some of the top questions pertaining to men’s dress shirts, like:
- What are the different types of dress shirts and collar types?
- How should my dress shirt fit?
- Dress shirt sizing chart
- Dress shirts by occasion
- How to care for your dress shirts
- How to wash your dress shirts
Ready to look, feel, and dress your best? Let’s get to it.
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What Are the Different Types of Dress Shirts and Collar Types?
Dress shirts, also known as button-ups, are staples to any man’s wardrobe. Though more formal than a tee shirt, dress shirts are versatile in various settings. On the casual side, you might pair a dress shirt with khakis or hybrid shorts depending on the weather.
Ultimately, the level of formality can depend on how you cuff, tuck, position the collar, and button your shirt (more on these later).
As you shop for size, it helps to consider the occasion. Common events for men’s dress shirts include:
- Date nights and dinners
- Work meetings or conferences
- Fundraisers or galas
- Theater performances and concerts
- Birthday parties and patio gatherings
- And so much more!
While it’s easy to think dress shirts are fancy, they can be dressed up or down as you see fit. There are four main types of men’s dress shirts; here’s what to know.
1. Classic Fit
Men’s classic fit dress shirts are the tried-and-true, original menswear. These shirts are classically worn under jackets and can present as baggy on their own.
2. Modern Fit
Unlike the classic fit, modern fit dress shirts are a tale of the times. They’re tighter in nature, but still roomy in the chest, waist, and arms. Similar to the classic fit, however, modern fit shirts can be worn with or without a jacket.
3. Slim Fit
Slim fit shirts are even tighter than the previous two styles, but not as tight as a skinny fit (as described below). Essentially, all of these styles exist to help you find that Goldilocks comfort level.
4. Skinny Fit
Skinny fit dress shirts are as close to skin-tight as it gets. They’re notoriously more fitted than other styles, specifically in the chest and arms. Skinny fit dress shirts are a trendier style for younger men and require precise measurements for optimal comfort.
Once you find the type of shirt that suits you best, you can decide how you prefer to wear the collar. Here are the top 7 ways to consider.
1. Forward Point
The forward point, also known as a straight point collar, is one of the most common ways to wear a collar. Angled cleanly on both sides, this look helps create length for those with shorter necks.
2. Cutaway
Cutaway collars are shorter and wider than forward points, a perfect choice for casual events.
3. Band
The band collar wraps around the neck in a wide shape, bound by one button at the neck. This is a great choice for casual events and a nice alternative to the pointed collar.
4. Long Point
The long point collar can be treated as a combination between the band and the forward point, if the forward point was longer. Essentially, the long point creates a layered look, as though the band were sitting underneath the pointed collar. Additionally, the long points have buttons, presenting a casual but classy look.
5. Short Point
The short point shares the same look as the long point, just, well, shorter! Both long and short point collars are polished but casual, with three buttons total: One on each point and one at the center of the neck.
6. Tab
The tab collar has a small, fixed tab in the center designed to create length and help push ties upward. It’s important to note tab collars shouldn’t be used without a tie.
7. Wingtip
Tab collars are to ties what wingtips are to bowties. Wingtip collars hug the bowtie and exist to help you look your best for black tie events.
As you can see, there are various ways to match your shirt type with your collar style. What works for you can depend on:
- The event
- The weather
- Your comfort level
- Your style
Ultimately, finding the perfect outfit depends on ever-changing variables, so it’s best to have a few options at all times. But once you get your basics down, everything else will fall into place.
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How Should My Dress Shirt Fit?
Ultimately, you’ll know which dress shirts fit best based on two things: how you look and how you feel. Let’s start with the former.
How You Look
Let’s revisit the four main dress shirt options and which body types typically work best for each.
Classic fit: Works well for larger frames and overall looser fit in the front body
Modern fit: Works well for broader shaped men who prefer accentuating their silhouette
Slim fit: Works well for muscular builds and flatter body types
Skinny fit: Works well for leaner and smaller body types
As you can see, there is nuance between each of these options, which is why your opinion matters, too! The decision-maker most always comes down to your personal preference. Which brings us to…
How You Feel
While feeling good matters the most, it still helps to keep an eye out for a couple of things to help determine your comfort level.
Generally, there should be enough room in the arms and stomach without too much extra fabric hanging around. The fabric should rest on the chest loosely when unbuttoned, though still close to the body, and a bit more snug when buttoned.
You’ll know the shirt is too tight if there’s pulling across the frontal body or if the buttons look taut. You absolutely don’t want to see pockets of your skin in between the buttons.
On the other hand, you’ll know the shirt is too loose if there’s no definition in any part of the body (arms, chest, stomach), and if the shirt looks bunchy.
A good test? Once you try on your dress shirt, move around a bit. Move your arms up and down, sit and stand, and mimic movements you would do while wearing it.
You don’t want to feel stiff and inflexible, nor do you want to feel as though you’re burdened by extra floating fabric.
Ask yourself:
- Can I feel confident in this dress shirt?
- Does it hug me in all the right places?
- Is there enough wiggle room, but not too much, to move around?
Dress shirts are more formal than a casual tee, in nature, so you want to feel a bit more buttoned up (literally!). However, comfort is still attainable here, so don’t hesitate to strive for both!
Men’s Dress Shirt Size Chart
So far, we’ve covered different types of men’s dress shirt types and which body types may resonate with each.
But, what about the actual size numbers? What about when you’re out at the store or shopping online and need to know which ones to snag? We’ve got your back. Check out the men’s dress shirt size chart for guidance below.
When sizing yourself for men’s dress shirts, two things matter most: neck circumference and arm length. It doesn’t hurt to have chest size as well, though not every retailer will require it. And the good news is…all you need to determine these numbers is tape measure.
Note that measuring these yourself may be a bit tricky, so don’t hesitate to reach out to a friend or loved one to help you. Take note of your measurements and keep them somewhere you’ll remember them for prime shop time.
Once you have these measurements, you’ll be able to read shirt sizes with ease. The first one is the neck circumference and the second is the arm length.
For example, 14/33 means the neck is 14 inches and the sleeve length is 33 inches. Sometimes, the size will be a range, which works for those who want some wiggle room.
Generally, seeing “small, medium, and large” on a shirt isn’t entirely helpful unless it’s paired with specific numbers. For a quick reference, here’s a standard men’s dress shirt size guide you can refer to:
*Small: 14-14.5” neck, 32-33” sleeve
Medium: 15-15.5” neck, 33-34” sleeve
Large: 16-16.5” neck, 34-35” sleeve
As is true for any other piece of clothing, note that sizes are designed to serve as guidelines. They may vary depending on the brand, so do your best!

Guide to Men’s Dress Shirts By Occasion
While it’s strategic to have multiple dress shirts in your closet, that’s simply the first step to formulating your dressy look.
Just as belts, bags, and jewelry can accentuate a feminine look, jackets, ties, and cuff links can accentuate a more masculine look.
Depending on the occasion, there are also different ways to style your dress shirt. Let’s take a closer look at some ways to wear dress shirts based on the occasion.
1. Black-Tie Formal
Whether for weddings, formal dances, or upscale galas, black-tie formal is a must-know in the fashion world.
To complete the look, include a black tuxedo jacket, French cuff links, a black bow-tie, and a solid or softly patterened white dress shirt.
2. Corporate Events
Though corporate environments are semi-formal to formal depending, there is typically more room to play with colors, patterns, and textures than at a black-tie formal affair.
Having a few looks can help you decide when to take the smart casual approach, cocktail attire, black tie, or white tie. Again, fashion lives on a spectrum, so use your best discernment here.
Casual corporate usually means sporting an unbuttoned shirt with an open collar, paired with formal jeans, or casual dress pants. For a more elevated look, go for a distinct collar or tie, polish with cufflinks, and finish with a jacket. Lookin’ good!
To distinguish your looks with intention, separate your daily corporate wardrobe from your special event wardrobe. This will help you know how to accommodate both flexible and formal dress codes.
3. Weekend Wear
For social events, casual outings, and evening attire, feel free to roll up those sleeves and kick back a bit. Pair any colored dress shirt with seasonally-appropriate pants and layer accordingly.
Note that color matters! Darker colors, by nature, are more formal, whereas lighter colors are versatile. How you dress yourself matters, as your pants and accessories together will send a message.
As you can see, dress shirts are simply the foundation. Use them, coupled with this men’s dress shirt guide, as your canvas to construct looks that hit every single time.
How to Care For Your Dress Shirts
Caring for dress shirts should always be top-of-mind, because investing in your wardrobe is an investment in yourself. That means dress shirt maintenance is part of the package! Here are some quick tips.
1. Wash White Dress Shirts Often
White dress shirts are the most versatile color and kind, so they need to be washed more often. Know that like other clothes, every time you wear a dress shirt, the fabric absorbs sweat and skin oil. If you don’t wash it after use, you may be in a regrettable position the next time.
2. Try Undershirts
Undershirts (either tank tops or t-shirts) are a helpful hack to keep dress shirts from expedited wear and tear. It’s often preferred to have a barrier between the dress shirt material and bare skin. Consider keeping multiple undershirts around to avoid daily laundry.
3. Iron or Steam
Dress shirts, though crisp upon purchase, are prone to creases and wrinkles. For that reason, irons and steamers will fast become your new best friends.
Make it a habit to iron or steam your dress shirts before wear for optimal finesse. Wearing a wrinkled dress shirt can deplete your efforts of looking nice.
Ironing can be a bit of an art. Ironing too close to the fabric can burn it, depending on the type. Steam is usually a better bet for sensitive materials, but hot water can also have a harsh impact.
To be safe, be sure to check the label for any special instructions. Now, onto washing!
How to Wash Your Dress Shirts
Similar to ironing, washing instructions can be specific. Generally, cold water works best for dark colors and hot water for light colors and whites.
Like other laundry, separate your lights and darks so as to avoid bleeding colors together. Wash on a delicate cycle with quality detergent and air dry to help the shirt maintain its original shape.
For materials that are more prone to shrinking, like cotton, these shirts may be pre-treated. Use extra caution and take it one step at a time. In the event of a fashion emergency, you can always consult a local dry cleaner or laundromat as well.
As is true for any new wardrobe venture, the beginning can feel a bit like trial and error. Simply follow the instructions and keep this guide to dress shirts handy. You got this!
Best Dressed
Thanks to this comprehensive guide to dress shirts, we have no doubt you’re well on your way to optimal wardrobe wisdom. No matter your age or fashion experience, there’s always a need for quality resources to help you refine your look.
Remember, intention is everything. Give yourself time to map out your looks long in advance. Consider developing a ritual—whether the night before the event, the morning of, or some hours prior—to set the tone for your look and mood.
Now, head over to Zappos to start drafting those looks! We can’t wait to see what “best dressed” means to you.