7 Best Dress Shirts for Men That Will Up Your Style Game

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William Barton Avatar by  William Barton | Last Updated:  Jul 21, 2020
Mizzen Kennedy

There aren’t too many fashion “must-haves” out there.

Sure, there are plenty of “nice-to-haves,” but when it comes to presenting yourself, a great dress shirt goes a long way.

I was at a wedding a few weeks ago, and I noticed a trend amongst the younger guys. The 20-24-year-old dudes showed up in a nice shirt, dress slacks, and a tie.

No jacket.

And you know what?

It looked great.

There’s no doubt that a suit or blazer are wardrobe staples. But it was nice to think back to those youthful days when my closet was barebones and a solid dress shirt was as formal as I could go with my budget.

My wardrobe has evolved since my early twenties, but one thing has never changed. A killer dress shirt is still a core essential.

Even the young guys know it.

We’re going to talk about how to style one, how to find the right fit and give you a list of our seven favorite shirts right now.

So whether you’re looking for a wedding or for work, we’ll give you everything you need to know to upgrade this wardrobe staple.

The 7 Best Dress Shirts for Men in 2020

Without further adieu, here are our seven favorite dress shirts right now.

1. Mizzen + Main Leeward

Mizzen Kennedy 1

Mizzen + Main’s Leeward collection is a great balance between classic menswear and modern fashion.

The trim fit and spread collar make for a versatile shirt that works on its own or paired with a suit.

Model Wearing Mizzen+Main Kennedy Dress Shirt Sitting Down and Smiling While Crossing Hands

We’ve tried the Kennedy and Malone colorways and we love the texture and fit.

This is the shirt for you if you travel a lot for work. It simply doesn’t wrinkle or crease. Even fresh out of the box, all I had to do was hit it with some steam and it’s stayed completely wrinkle-free.

Mizzen Knit with Kennedy Upstairs 2 1

If you’re used to packing everything into checked luggage, the Leeward collection is your best bet. Great fit, all-weather, and no-wrinkles makes for a great travel companion.

2. Apposta CoolMax

Model Wearing Apposta Coolmax Twill And Standing On Stoop With Shirt Tucked Into Jeans

If you read our guide on taking measurements and couldn’t get enough, Apposta might be for you.

Apposta makes all-custom shirts that you design. In fact, there are more design variations than there are humans on Earth.

We really liked the process of creating our own dress shirts from scratch. One issue to note with these—the arms did run a bit long. They say it takes seven or eight washes to fully shrink. If you go this route, we recommend you order your sleeves a bit shorter than your measurements.

If you don’t want to go through the whole process of making your shirt from scratch, try their CoolMax. We especially like it on hot, sunny days because of its SPF 50+ rating.

3. Charles Tyrwhitt Extra Slim White

CT shirts

I visited London back in 2012, and I was shocked. I didn’t know England had a mandatory, national uniform. I didn’t check with any officials, so this is all unverified. But from what I could see, every adult male between the ages of 26 and 42 wore a navy suit with a white, semi-spread collar dress shirt. Tie optional.

Do you know where all those Londoners got their shirts? Charles Tyrwhitt.

This growing company has plans to expand London’s national navy suit agenda, with 12 brick-and-mortar shops in the States already. Check out their Extra Slim white dress shirts (pairs perfectly with a navy suit) and become a loving subject of the royal family today.

4. Buttercloth Herjavec Collection

Buttercloth dress shirt

One man’s mission to create the world’s softest shirt landed him on national television a few times.

Buttercloth has exploded since landing a deal with Robert Herjavec on ABC’s Shark Tank. He’s even developed his own line.

We gave Buttercloth a try for ourselves and loved the fit. These are a great option for looking sharp on casual Friday. The added flair on the inside of the collar and cuffs sets Buttercloth apart.

If you want a classic look but don’t want to sacrifice your individuality, check out Buttercloth.

5. Mizzen + Main Spinnaker

Model Wearing Mizzen+Main Beckett Dress Shirt with Hand in Pockets and Holding a Folder

Anyone here live in a warm climate?

If you do, check out Mizzen + Main’s Spinnaker collection. This range is M + M’s most stretchy, comfortable, moisture-wicking option.

When we gave the Spinnaker a try, we forgot all about the fact that we were wearing long sleeves—it was that comfortable. Darts in the back keep it slim and streamlined. We loved the fit, and it works especially well tucked in.

Model Wearing Mizzen+Main Beckett Dress Shirt While Walking Out of a House and holding coffee and a folder

If you need a dress shirt you’re not going to sweat through, check out Mizzen + Main’s Spinnaker line.

6. Bonobos Daily Grind

Bonobos DS

Bonobos has a wide range for guys looking to solve their workday woes. Their Daily Grind line is a collection of nearly 50 simple colorways you can rock in the office.

They know when to go loud and when to tone it down. With their dress shirts, Bonobos doesn’t go full bodacious. Sometimes, simple is all you need.

7. Brooks Brothers Milano

brooks brothers dress shirt white 1

These guys have been in the shirt game forever. Well, since 1818. Abraham Lincoln had a coat from Brooks Brothers.

They have unique collar options that aren’t too common, like this Milano stretch shirt with a clubbed collar. While the styles are a little “older,” some nights just call for a little more refinement.

You know, the nights where you sit back in a high-back chair with a musty cologne and read important passages from a leatherbound book.

How Dress Shirts Are Measured

Dress shirts have four important measurements. These are:

  • Neck Size
  • Chest Size
  • Waist Size
  • Sleeve Length

Other important measurements are:

  • Seat Size
  • Bicep Size
  • Shoulder Width
  • Cuff Circumference

You’re not likely to have control over these last four measurements unless you’re going to a bespoke shop or tailor. For that reason, we’ll only cover the big four mentioned above.

Neck Size

Neck size is the circumference of the collar with the top button done. Typically, neck sizes range from 15.5” on the small side to 18.5” on the large size.

When buying off the rack at a department store, neck size is the first measurement I look for.

I’ve noticed that most of the time if you get the neck right, everything else follows suit.

So if you don’t want to take the time to measure out your torso (or you’re operating solo), at least measure your neck.

My neck is 16.5”, which puts me somewhere in between a medium and a large.

If you’re like me and are in between sizes, you might need to do a little more digging to figure out what fit will work best for you.

Chest Size

Chest size is the second most important measurement. But you’re going to need a friend to help you with this one.

You’ll want to measure the fullest part of your chest, so you need a tape measure to run under your armpits.

Most companies judge their sizing based on actual body measurements—not the measurement of the shirt. That means, if you have a 40” chest, get a shirt with a 40” chest measurement. Some resources out there tell you to add a few inches, but if you do, you’ll end up with an oversized blanket.

Sleeve Length

When measuring your sleeve length, you’ll actually be adding two measurements together.

First, measure from the base of your neck to the end of your shoulder (the very top of your arm). After you’ve got that, measure the length of your arm to where you’d like the cuff to sit.

Add those two numbers together and round up to the nearest available measurement, and you’ve got the perfect sleeve length.

A quick note on measuring for sleeve length: stand as natural as possible when getting this measurement. That means your arm will have a slight bend to it. If you unnaturally straighten your arms or bend them too much, you won’t get an accurate measurement.

Waist Size

Unless something is terribly wrong, waist size shouldn’t be a deciding factor when buying a dress shirt. You’ll get enough information to find something that fits great by knowing your neck, chest, and sleeve sizes.

If the manufacturer has any idea what they’re doing, they’ll nail the waist size.

Shirt Sizing Chart

Mizzen + Main has a great sizing chart that shows what your measurements are for both their trim fit and standard fit shirts. These measurements work with many brands, too, though each brand has its own unique fit and style.

Screenshot 2019 10 22 at 8.26.01 AM
Screenshot 2019 10 22 at 8.27.07 AM

If you don’t feel like busting out a tape measure and marking down your sizes, I don’t blame you. You can go to a tailor and get your measurements done and have them tucked away for reference.

But as a quick guide, I’m 6’2”, and weigh between 180 and 185lbs. I have an athletic frame, meaning my chest and waist are roughly the same widths.


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I went with a Trim Medium, and it fits great. But looking through the measurements, I’m right on the line between medium and large. If you’re like me, you’ll just have to choose if you want your shirt a little more snug or loose.

And with most companies, if you mess up your sizing the first try, you can exchange for the right fit.

Different Types of Collars

The collar of a shirt defines its style. Some collars are more formal, some collars are casual. A lot of people overlook the style of collar, but that’s a big mistake.

Knowing what style you’re going for will help you choose the right collar for you. These are the four most popular types of collars.

Straight Point Collar

The straight point collar is the most commonly available. It’s a slightly older looking style, but it’s perfect for gents with wider faces. The narrow opening in the front will elongate your facial structure.

Straight point collars look best with a tie. Depending on the fabric of the shirt you choose, this collar style can work in a formal or casual situation.

Spread Collar

The spread collar is the modern alternative to the point collar. These collars allow you to showcase wider tie knots, like a Windsor.

spread windsor
Photo Credit: Effortless Gent

The spread collar will visually widen your jaw, so it’s a great option if you have a narrow face.

Button-Down Collar

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These veer toward the casual end of the dress-shirt spectrum. While you can wear a button-down with a suit and tie, I like to layer them with a sweater or a vest.

Every guy should have a great button-down—they’re so versatile. I recommend investing in one that fits you well. Because you can wear it on Friday nights and Sunday mornings alike, you’ll get your money’s worth in no time.

Band Collar

Less Zoomed Close Up Of Model Wearing Apposta Coolmax Twill - Chest

Band collars are the most casual option and are usually only found in chambray or linen shirts. It’s a throwback to when men used to attach turndown collars with pins. Now, it’s purely a style choice.

Band collars look great on slim guys and work well underneath a blazer for the rest of us.


Wherever you are with your wardrobe, you’re going to need at least one top-of-the-line dress shirt.

You don’t want to be like me at my sophomore year homecoming—wearing the world’s thinnest, most ill-fitting thing eight dollars could buy. They called me “nipples” for weeks.

A great dress shirt will last you a long time, and when you get one that fits right, you’ll find yourself wearing it more than once per week.

These seven winners are sure to help you stand out whether you’re looking to be the most stylish guy in the office or you need a special touch for a date night.