Some of the best men’s dress shirts in the world are also the comfiest. From high-quality styles to more affordable options that you can get for under $50, we have rounded up a range of different designs for men of all shapes, sizes, and budgets. Whether you wear them for work or social occasions, there are lots of designs that are a pleasure to wear from brands using the latest high tech comfort fabrics to time tested classics made from the finest cotton. We have found the best dress shirts that are comfortable, durable, and suitable for everyday activities or more formal events.
Ministry of Supply Apollo
If you are serious about finding a comfortable style, you are going to want to check out some of the start-up brands that are redesigning office wear using materials that are typically used in sports performance shirts. First up is the Ministry of Supply and its Apollo design. Apollo is an excellent style if you have any issues with overheating in your clothes, as it uses a material that regulates body temperature. So they are especially useful if you have to dress up in the summer for a wedding or formal event and you tend to sweat a lot. The feel of the material is breathable, comfortable, and soft. It is also wrinkle-proof, so you don’t need to iron it. Most men find the fit to be pretty good regardless of your body type, and the fabric drapes well while the stretch has enough give to make them easy to move in. It’s temperature-regulating material also make this an exceptional all-around travel option since they won’t crease. They come in a slim or a standard fit in sizes XS to XXL in eleven different color options.
Available from Ministry of Supply.com
Van Heusen Men’s Poplin Regular Fit
If you aren’t a fan of the slim fit styles and are looking for a budget option, a favorite among many men is the Van Heusen Men’s Poplin Regular Fit Solid Point Collar Dress Shirt. If you get the sizing right, this can be a fantastically comfy style that you won’t dread wearing. The fabric is a 65% polyester and 35% cotton blend, and it features a point collar with regular cuff. It also has a chest pocket, which some men like and some not so much. It is an easy to take care of style because you can machine wash it, and it is easy to iron. This Van Heusen design is a basic option with a relatively thin fabric, so it works well in warmer months or climates. The material isn’t the softest, but the comfort lies in the relaxed fit, so if you are interested in this style, you will probably want to wear a thin t-shirt in soft cotton to add to the comfort level. This is an appropriate style if you have a larger frame and want a comfortable style at a reasonable cost, that comes in lots of colors.
Available from Amazon
Express Slim Solid Wrinkle-Resistant Performance Dress Shirt
Express is a good place to find a classic button-down for work. Their best style is The Express Slim Solid Wrinkle-Resistant Performance Dress Shirt that is known for being super comfy and for looking very sharp and professional on most body types. They come in several fits, including extra slim, slim, and classic, and they are available in 17 attractive modern colors. Men love the fit, fabric, and the fact that this style washes and dries well. This is a performance design, so it is breathable, flexible, and non-wrinkly. They go on sale fairly often, so you will want to wait for a deal to get the best value since they are a tad pricey at full price.
Available from Express
Nordstrom Trim Fit Non-Iron Dress Shirt
Not surprisingly, Nordstrom is a wonderful go-to store for business and formal wear that is usually good quality and pretty stylish. If you aren’t familiar with their house brand of shirts, you may want to check them out because they are a pretty good value for the price, they don’t wrinkle or stain, and they are well made. They also wash and wear well, with the collars remain crisp, making them a great professional work option. One of the Nordstrom brand’s most popular style is the Trim Fit Non-Iron Dress Shirt. It is 100% cotton, has a straight collar with removable collar stays and adjustable button cuffs.
Available from Nordstrom
The Twillory Leader is another fantastic option that is super comfy because of the slightly stretchy material that is wrinkle-free, moisture-wicking, and breathable. This performance style also comes in a good range of neck and sleeve measurements that you don’t always find in performance styles (sometimes the sizing is a bit more limited.) It comes in tailored, extra trim, or traditional sizing and has the interesting feature of a different color inner collar. The inner collar is soft and adds to the overall luxe feel of the shirt; also, it doesn’t show the dirt or grime that can sometimes show on collars.
Available from Twillory.com
If you are looking to splurge on a high-end classic brand that is also known to feel great to wear, you may want to check out the Eton Dress shirt. The company is from Sweden and is known for using ultra-comfy cotton and easy-care dress options. They have a vast range of fits and styles for all types of men and all kinds of situations. They come with an eye-popping price tag, but fans of this brand find the cost to be worth it.
Available from Nordstrom
Calvin Klein Men’s Slim-Fit Non-Iron Performance Herringbone Point Collar Dress Shirt
A trendy comfort style, especially for younger men, is the Calvin Klein Slim-Fit Non-Iron Performance Herringbone Dress Shirt. This pick works well for both the office (if it is a more formal or professional setting) or for special events like a wedding or graduation when a more dressy look is required. It is made with a non-iron material, and the fit is slim cut. Since it is a performance style, it is moisture-wicking, and it is easy to wash and dry. It is also relatively bulk-free if you are wearing it under a suit jacket. The shirt we are linking to is a point collar, but this style is also available in a spread collar if you prefer. The material is 100% cotton, and it is available in a few different modern colors. Overall this is a lightweight, trendy, and moderately priced style that is great for slim people.
Available from CalvinKlein.com
Mizzen + Main Trim Fit Men’s Button-Down
Mizzen+Main is one of the few shirt brands that is manufactured in the USA. They have a lot of different styles in various patterns, colors, and fits, with the Mizzen + Main Trim Fit Men’s Button Down Shirt being an excellent style to start with. This is a wonderful option if you like a form-fitting design, and you have an athletic built frame or if you have a difficult to fit frame. The material is very lightweight and comfy, but you need to make sure you follow washing instructions to prolong the life of the garment and to make sure you don’t lose the non-iron feature of the material. Men who own shirts from Mizzen+Main say they feel super cool (temperature-wise) and breathable, lightweight, and stretchy. These designs are very versatile since they feel like athletic wear, but you can wear them for work or dress them up for a night out.
Available from Mizzenandmain.com or Nordstrom
Eagle Men’s Classic-Fit Stretch Collar Non-Iron Solid Dress Shirt
The Eagle Men’s Classic-Fit Stretch Collar Non-Iron Solid Dress Shirt is another fantastic department store option that isn’t slim fit, so it is excellent for those with larger frames that prefer a more relax classic look. It has a standard stretch collar and is a wrinkle-free design that you shouldn’t have to iron. Eagle has been around for a very long time, and they still make a high-quality shirt that has a devoted following. Eagle fabrics tend to be a little heavier weight than other brands, so you usually don’t have to worry about them being so thin that you have to wear an undershirt.
Available from Macy’s
Ludlow from J Crew
The Ludlow is a trendy style that is easy to find at your local J Crew. It comes in extensive neck/sleeve sizing, so it is not too hard to get a good fit. Like most J Crew suits, the Ludlow is perfect for helping you look professional and crisp at work. It is known for washing well and not getting wrinkled easily. The Ludlow is comfortable and good quality and is perfect for year-round wear at the office.
Available from J Crew
Ledbury The Fine Twill Spread Dress Shirt
Ledbury’s Blue Fine Twill Spread is a style that is known for its soft yet thick Italian-woven, 100% cotton twill fabric that is super comfy to wear. You can get it in a classic fit or a tailored fit with a spread collar design, and standard barrel cuffs. The material is relatively thick, so this isn’t a good option for warmer climates. The standout feature of this Ledbury style is the collar that keeps it’s shape nicely, even when not wearing a tie. With or without a tie, this is an excellent option for the office.
Available from Ledbury.com
Brooks Brothers is a dependable classic place to get really well made and good quality styles that last a long time. They come in six fits: extra slim, slim, regular, classic, relaxed, and specialized, and most styles come in super-soft Supima®, Egyptian and Sea Island cotton, designs in different weaves like oxford, broadcloth, and twill. Brooks Brothers offer three collar styles: forward point, button-down, and English spread. The cuff styles you can get are: barrel, mitered, and French cuffs. They also provide the option to “Design Your Own” custom styles, which is pretty cool. Brooks Brothers have frequent sales on the shirts, so it is worth waiting for the deals if you can get a multibuy offer, or they sometimes also have reasonable prices on their clearance merchandise.
Available from Brooks Brothers
The Tie Bar
Tie Bar’s dress shirts are well worth a look due to their moderate price ($55 or three for $140) and huge selection. They offer both styles that need to be ironed as well as quite a range of non-iron options. They come in a massive variety of colors; the neck sizes go from 14.5″ to 18.5,” and they have three different sleeve length options. You can get fits in standard or trim, and the collar comes in a button-down, point or semi-spread, and the cuffs available are convertible, french, or standard. So there is something for everyone, and while you are shopping, you can pick up a few ties as well.
Available from Tie Bar
TM Lewin is a U.K brand that makes excellent shirts that won’t break the bank. It is worth checking out the clearance section on their site since they often have terrific deals in the $30 price range. The regular price is around $79 per shirt, but they offer multibuy options to bring the price down a bit. Generally, the TM Lewin designs are made with good quality cotton and come in a wide range of patterns and colors. If you do the multibuy or get some of the sale styles, you are getting exceptional quality for the price you are paying. It does have to ship from the U.K, but the rates and shipping times aren’t terrible, and they have a strong return policy (although it may take a little while to ship back to the UK).
Available from TM Lewin
Charles Tyrwhitt Shirts
Staying with the British brands for a second, Charles Tyrwhitt’s men’s dress shirts are very similar to the TM Lewin styles listed above, just slightly more expensive. They have a good clearance section as well and also offer the discount if you do the multibuy option. Charles Tyrwhitt’s designs are generally a good comfort option because many of the designs are made from ultra-smooth cotton and available in your choice of collar size, sleeve length, cuffs, and fit, so the better it fits, the nicer it will feel to wear. They have four fits: classic, slim, extra slim, super slim. Their collar sizes go from 14″ to 20,” and sleeve lengths go from 32 to 38″. In their regular dress styles, they have four collar styles button-down, classic, extreme spread, and spread. The cuffs can be french or button; some styles allow you to add an option breast pocket if you like. This is also a brand that offers incredible quality in this price range.
Available from Charles Tyrwhitt
What to look for:
To ensure you get a style that is the most comfortable for your body, it is essential to focus on a few things when shopping. The following are what you need to keep in mind:
Sizing– To figure out your size, you will need to measure your neck and your sleeve length. To measure your neck you can either measure the collar of a comfortable shirt you already have to see the size or take a measuring tape and gently wrap around your throat area but keep a suitable distance between your neck and the measuring tape to allow for a bit of space between your neck and the collar. A lot of men find button-down styles to be uncomfortable because they get the wrong size neck, and it is too tight. If you have had a problem with this in the past, maybe try going up a size in the neck to see if it feels better.
To measure your sleeve length, measure from your wrist to the center part of the back of your neck along the outside of your arm and over your shoulder.
Color and Patterns– You can get all kinds of shades of formal and dress styles, and most are fine for almost any occasion. If you aren’t sure about colors and you are shopping for a formal event, solid colors are usually best. For social occasions that aren’t super formal, pinstripe or patterns can be a fun option. If you have to wear a dress shirt for work, solids or a light pattern are usually fine.
Collar-There are a bunch of different collar styles: point, semi-spread, spread, button-down. Some brands have different names for the same type of collar; it depends on the brand how they label it. For this post, most of the picks are a standard spread design (traditional) that you can use for most sizes of tie knots, we also feature a few options with a point collar that has a slightly narrower spread.
Iron vs. Non-iron – Nobody likes to have to iron their clothes if they don’t have to; this is clear from the massive popularity of non-iron and wrinkle-free designs that flood the market. These types of shirts are much less work than a style that doesn’t have the non-iron feature, but if you have skin sensitivities, be aware that non-iron fabrics are dipped in formaldehyde to keep them looking smooth. Most people won’t be bothered by this, but it is something to consider if you find the texture or feel of non-iron material to be irritating.
Fit– Good fit (which is surprisingly hard to find) makes a shirt much more comfortable Most brands have at least two fits, some have around four fits. It can be a bit confusing figuring out what fit is best for you. The best thing to do is to read any explanations of fit from the brand or manufacturer that is available. If there is no description available the general type of fits are: traditional/classic fit (looser and more relaxed ), modern fit (a bit slimmer than traditional), slim fit (a trendy style that is a close fit to the body with a tapered waist and fitted torso), extra slim fit (more trim than a slim fit). You can also get athletic fits that are great if you are muscular and have a trim waist.
Fabrics– Most of the most pleasant feeling fabrics are either the 100% cotton, cotton with a slight polyester blend, or the newer performance fabrics that contain a little bit of Lycra or Spandex to give stretch and sweat-wicking properties to the design. Thicker weight cotton can be suitable for the winter if you are looking for an extra level of warmth. Regular cotton fabric is usually fine for most occasions. Performance fabrics are great for the hot days of summer due to the sweating wicking and temperature regulating features.
Budget– You can get shirts in prices that range from $15 up to $350 and beyond. If your budget is tight check out Stein Mark for tonnes of designer brands usually around $30.
Easy Care- If you like your clothes to be low maintenance, make sure any style you choose is machine washable for easy care and no dry cleaning required.
Cuffs- There are a few different types of cuffs, but the most common are barrel (button) cuffs where the one side goes over the other, and you button it closed with either one or two buttons. Similar to barrel cuffs are mitered cuffs that have a 45-degree angle cut on the corner of each cuff. The other style you should know is the French cuffs, which require cuff links. Frech cuffs are sometimes worn with business suits but more commonly with black tie.