The 9 Best Men's Dress Shirts of 2019

A simple way to look sharp

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Whether you are headed to the office or a night out on the town, it’s important to look and feel your best. And depending on where you work, that could mean wearing a dress shirt for five days a week, if not more.

If you’re in the market for a dress shirt, don’t just head to the mall and pick the cheapest one off the shelf. Choosing the right shirt means weighing out several factors like fit, material, cost, and style. Follow along with this guide to learn more about picking the best men's dress shirt for yourself or a special man in your life.

Fit: Some shirt makers offer shirts in slim, regular and husky cuts. Find a shirt that is flattering on your body type: Slimmer men should not swim in a large shirt, and larger men should not squeeze themselves into something too small for their size.

Material: Shirts can be made of cotton, linen, lycra, polyester, rayon, silk and more. Some fabrics hold up better for longer, while others offer more flexibility or shine. Try a few different kinds of shirt until you find a material you like.

Style: One style does not necessarily fit all occasions. Find the right look for the right places. Work shirts and nightclub shirts generally look different, and that’s a good thing.

Cost: Cheap men's dress shirts start at under $10 and high-end shirts can easily exceed the $500 price point. You don’t have to spend an arm and a leg for a well-made shirt, but investing in a little quality can go a long way.

Other features: Non-iron shirts are one of the best inventions in the history of men’s fashion. Also look at the buttons, cuffs, and collar to find the right shirt for you.

Make sure you know your real dress shirt size before ordering

One last tip before we get to the best men’s dress shirts: it is important to find a shirt that actually fits you. If you don’t know your size, go to a local department store or tailor to get your measurements. You’ll need measurements for your neck, sleeve, chest, and waist to find the perfect shirt. While neck and sleeve are the two most important measurements for ordering dress shirts, don’t forget to consider the overall fit as well.

Best Overall: Brooks Brothers

Brooks Brothers
Courtesy of Brooks Brothers

Brooks Brothers is the classic American dress shirt company. It makes a range of clothing for men, women, and kids, but its primary focus is menswear. That includes very high-quality dress shirts.

You can buy Brooks Brothers shirts online, in Brooks Brothers stores, or in Brooks Brothers Factory Outlet stores. You know they focus on dress shirts first, as that is the #1 category listed on the Brooks Brothers website.

Brooks Brothers dress shirts come in slim, fitted, classic, and relaxed fits. Prices range from $250 for the most high-end shirts and go down to $69.50. But you may be able to find coupons, deals, or sales to save a lot on those sticker prices. Regular shoppers should join the My Brooks Rewards program to earn points redeemable at Brooks Brothers as well as exclusive services and early access to new products and sales.

Best for Young Professionals: Charles Tyrwhitt

Charles Tyrwhitt
Courtesy of Charles Tyrwhitt

Charles Tyrwhitt is basically the uniform of London's finance and law professionals. The company is based in the UK, but it is easy to find their shirts on this side of the pond as well. Check out their brick-and-mortar stores in New York, Chicago, and Washington DC, or if you live far from those cities, you can easily customize your order of men's dress shirts online.

Charles Tyrwhitt offers a range of men’s fashions, but dress shirts take the prominent position on its website and in stores. They are high quality, comfortable, and come in fun and modern styles and designs. Young professionals can’t go wrong with this brand.

The best deals are available when you buy multiple shirts, which can bring down prices by as much as half from the list price. Shirts range from $29.50 on the low end to $139 on the high end. They are great for everything from a day in the office, to a wedding, to a night on the town.

Best for Baby Boomers: JoS. A. Bank

JoS. A. Bank
Courtesy of JoS. A. Bank

Joseph A. Bank (styled as JoS. A. Bank) is a major men’s clothing chain across the United States. The company merged with Men’s Warehouse in 2014, ending the independence of a store tracing its roots to a shop opened by the Bank brothers in Baltimore in 1905.

Don’t walk into a JoS. A. Bank store and pay full price — they're famous for their discounts. Dress shirts come in slim, tailored, or traditional cuts. As of this writing, most shirts have a price tag around $90, but after “sale” savings the actual price was about half that list price.

Best for Classic Styles: Ralph Lauren

Ralph Lauren
Courtesy of Ralph Lauren

Polo and Ralph Lauren branded shirts are a classic style (the term “polo shirt” has become synonymous with any short sleeve, knit, collared shirt). But this manufacturer goes far beyond the classic short sleeve polos — they also make high-quality, long-sleeve dress shirts.

Ralph Lauren dress shirts come in both formal and casual styles. As of this writing, the cheapest Ralph Lauren dress shirts cost about $60 on sale, and the most expensive high-end dress shirts go for over $600. The priciest shirt on the website is the Purple Label End-on-End Shirt for $695.

Ralph Lauren gets consistently high ratings for quality, so you know you will end up with something that lasts if you shop at Ralph Lauren. And if those $600+ price tags startled you a bit, don’t worry too much. Many of their shirts in the $60-$150 range offer great style and quality without emptying your wallet in the process.

Best Budget: Costco

Costco
Courtesy of Costco

Costco already sells a bit of everything, so why not dress shirts too? Costco’s Kirkland brand offers quality dress shirts for (much) less — as of this writing, all Kirkland Signature men’s dress shirts carry a $17.99 price tag. While you won’t get quite the same quality with these bargain shirts, you could save a small fortune stocking a closet at Costco compared to the more high-end sellers on this list. And the Kirkland quality is still decent, offering great value for the price.

Shirts come in traditional and tailored fit styles and offer a limited range of color and collar choices. Also, like most Costco purchases, they are easy to return if they don’t work out for your needs.

Best High-End: Thomas Pink

Thomas Pink
 Courtesy of Thomas Pink

These high-end dress shirts come from London in business, casual, evening, and linen styles. You can expect to pay $130 to $300 for most shirts from this brand.

If you can afford it, Thomas Pink offers a wide enough range of styles to make up an entire dress shirt wardrobe. It offers shirts perfect for everything from a business casual day at the office to a formal black-tie event. Shirts come from several collections which include the convenient non-iron styles.

Shopping at the Thomas Pink website is fun, with filters to zero in on your favorite new shirt based on the collar style, collection, fabric color, cuff style, pattern, and business, casual, and evening styles. And if you love the shirts, you can also find other men’s and women’s shirts and accessories to complement your collection.

Best Casual: J. Crew

J. Crew
Courtesy of J. Crew

J. Crew offers high-end fashions for men and women, both online and at their multitude of retail stores across the country. Online shopping is convenient, but there is some value in going into a store where you can try on shirts before you buy.

When you buy men’s dress shirts at J. Crew, you get a good balance of style and cost. For example, the new Ludlow shirts run $69.50 each or $150 for three. J. Crew shirts come in both classic and slim fits, so you can quickly find something flattering for your physique.

Best Everyday Shirt Under $100: Bonobos

Bonobos
 Courtesy of Bonobos

Bonobos offers its Daily Grind Wrinkle-Free Dress Shirts for $98 each or $225 for three. Bonobos dress shirts come in three different fits, four collar styles, and a variety of fun and unique patterns that you'll enjoy wearing to work, happy hour, family dinner, or a night on the town.

Bonobos offers other styles and lines of shirts over the $100 mark, but getting something that fits well, looks good, and never needs an iron makes the Daily Grind perfect for daily use.

Best Multi-Brand Marketplace: Amazon

Amazon
Courtesy of Amazon

If you want to look past individual brands and shop somewhere that offers a huge number of shirts from many different brands in one place, you can click over to Amazon. Prime members will enjoy the Prime Wardrobe program that allows you to try items for up to 7 days for free at home.

Popular brands on Amazon include Van Heusen, Calvin Klein, Reaction from Kenneth Cole, and Amazon’s own brand Buttoned Down.