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Finding the right dress shirt can be challenging. It might not seem like there are many variables, but the truth is, when it comes to fabrics, fits, cuts and colors, the possibilities are nearly endless. It makes you wonder how you ever got by purchasing one before.

Whether you are attending multiple weddings this summer, or simply want to look nice for your bi-monthly splurge at the Olive Garden. Here are the 5 best men’s dress shirts for every occasion, how to style them and what to look for in a dress shirt. 

What to Look For in a Dress Shirt

A lot goes into a solid dress shirt, and you can get a lot out of one if you know what you’re looking for.  

Quality is a very broad term, but it covers everything from material to fit. Name brands don’t typically become universally known and loved for bad quality pieces, so if you are picking up something from Brooks Brothers, Ralph Lauren or Calvin Klein, it’s safe to say that the quality will be there along with a steeper price tag.

Does that mean that you can’t find quality in less expensive or lesser-known brands? Not at all.  

Although I do believe there is a difference between an $80 shirt and a $20 shirt, It doesn’t mean the latter is bad but most likely that it doesn’t have the detail or branding of a more expensive option.  

The secret to a great dress shirt is the fit. When you come across a garment that fits you well, it’s easier to look past anything you might not like about it. 

Consider this chart when you’re shopping for your next one:

Infographic of How a Shirt should fit
Editorial Credit: RMRS

It shows that the perfect length shirt should drop a few inches under your belt line to stay tucked in if you raise your arms. And a perfect sleeve length should cover just past your large wrist bone. 

How to Wear a Dress Shirt and Look Confident

Next time you’re going for a confident and casual look, it’s as easy as styling with a pair of jeans.  

Keep it simple,  slim and fitted jeans are the perfect compliment.  

Stay away from anything too baggy and especially anything ripped or bedazzled.  Feel free to tuck it in, or go untucked if you’re feeling dangerous.  I’ve heard rumors of the “half-tuck,” but try that at your own risk.

On the other side of the spectrum, if you’re going for a more formal menswear look or appropriate cocktail attire, it’s pretty obvious you want to stay tucked in. Lean toward a point collar, and a dark blazer to wear over.  It’s easier to achieve this look than you think.

The Best Overall Dress Shirt: Ralph Lauren Long Sleeve Classic Fit Oxford Shirt

Ralph Lauren Long Sleeve Classic Fit Oxford

In a popularity contest, Ralph Lauren’s Oxford Shirt would take the cake. You really can’t go wrong with this piece, and I would argue that if you’ve bought one, you have most likely purchased a couple more since your first shirt.  

This dress shirt comes in over 40 different colors and patterns, so there is no lack of options.  New, these dress shirts run about $95, but a brand name like Ralph Lauren means quality and consistency.

The Best Non-Iron Dress Shirt: Brooks Brothers Stretch Madison Classic-Fit Dress Shirt

Stretch Madison Classic-Fit Dress Shirt, Non-Iron Poplin Ainsley Collar Gingham

You really can't go wrong with any dress shirt from Brooks Brothers, but the Stretch Madison Classic Fit takes wrinkle resistance to the next level.

Made with elastane, Supima cotton and a medium spread collar, this high-quality shirt will help you look put together for any occasion for $114. It is also made with pucker-free seams and has a chest pocket. If you want to find other non-iron shirts they have a fitted and slim fit dress shirt too with the same look and feel.

The Most Comfortable Dress Shirt: Kenneth Cole Reaction TECHNI-COLE™ Slim Fit Solid Dress Shirt

Kenneth Cole Reaction TECHNI-COLE™ Slim Fit Solid Dress Shirt

The TECHNI-COLE™ Slim Fit shirt offers up superior comfort with this line of button-downs.  

These shirts are sewn with an elastic thread that allows for a wide range of motion, and if that wasn’t enough, the material used is woven with 4% spandex. 

This is a perfect option for anyone who might feel out of place when they’re dressed up. The comfort behind this shirt will make you forget you’re wearing anything with a collar.

At $69.50, this is a nice middle of the road option that won’t set you back as far as some others.  

The Most Slimming Dress Shirt: Calvin Klein Slim-Fit Non-Iron Herringbone Dress Shirt

Calvin Klein Slim-Fit Non-Iron Herringbone Dress Shirt

Another staple piece, this Calvin Klein point collar dress shirt is something to consider.  

Research shows that a point collar can add a slimming effect for rounder faces, but regardless of your shape,  anyone who puts one on can experience a more classic look. Think Don Draper of Madmen; exciting right?  Is it time for an afternoon Bourbon?

Another notable function of this dress shirt is its non-iron fabric.  I love the idea of being well dressed and only putting in a fraction of the effort to get there.

This name brand shirt clocks in at $75 and comes in 13 different colors. 

The Best Amazon Dress Shirt: Goodthreads "The Perfect Oxford Shirt"

Goodthreads "The Perfect Oxford Shirt"

On a less expensive note, Amazon’s Goodthreads brand has an impressive option for someone who is on a budget and doesn’t purchase anything, not on “Prime.”  

Their “Perfect Oxford Shirt”  runs about $25, and although these shirts are only offered in alpha sizing, they are still highly regarded for having an excellent fit. 

A Heritage wash gives the garment a “lived-in” feel, so that you can skip the stiffness of a typical brand new dress shirt.

Pick this one up in blue, indigo, pink, purple, turquoise or white.

The Best Budget Dress Shirt: Kirkland Signature Traditional Fit Dress Shirt 

Kirkland Signature Traditional Fit Dress Shirt 

If I told you it was possible to buy the perfect dress shirt in an exact sleeve length for under $20, would you believe me?

Costco’s brand Kirkland makes that possible with its line of dress shirts. The quality behind these button-downs goes unmatched for the price.  

Imagine getting a name brand fit for a literal fraction of the price (considering you have a Costco membership).

Besides the unheard-of fit these shirts offer, they also repel water and oil-based stains. An 8th button on the front placket will not leave any gaps in the shirt if it happens to pull up. A steal if you ask me!


The truth is that what ultimately makes a good dress shirt, is the way it fits you.

Finding a dress shirt that is breathable, fits in your price point and style is the most important thing when choosing a buttondown dress shirt. If you aren't big on ironing, look for buttondown shirts that are non-iron. Also make sure you pay attention to the collars. There are poplin collars, button down collars, point collars and more.

If you want to try on a dress shirt before purchasing, head to a local department store, like Nordstrom, and try on a few different options. You might find out you look better in the extra slim fit versus the slim fit.

By playing to your strengths and selecting a dress shirt that compliments your physique, you will be making the right choice.

You might also be interested in: The 4 Best Loafers For Men In 2020 [And How To Style Them]

The best men’s dress shirts for every occasion: 

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Posted 
Jun 23, 2020
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