Men’s Dress Shirts that are Actually Comfortable to Wear

Bonobos Dress Shirts can easily transition from dress to business casual, depending on how you wear it. Since it is Bonobos, the sizing options are pretty extensive, so almost everyone can get a good fit, which is the first step to finding clothes that you feel comfortable in.

Reviewers rave that the fabric is silky smooth and thick enough that you can’t see through the shirt and don’t need an undershirt. You can get this style in a huge range of nice patterns and colors perfect for dressy casual or with a suit and tie.

The Rhone Commuter Shirt is a shirt you will want to check out if you are serious about being comfortable. Rhone is so confident in this style that they market it as ‘The Most Comfortable Dress Shirt Ever Made.’ It comes with a 45-day guarantee for comfort.

The four-way stretch lightweight Italian fabric is the key feature of this shirt that ups the comfort level significantly. It is also able to natural wrinkle release comfort and is moisture-wicking.

Banana Republic is a great retailer if you are looking for reliable quality dress shirts. Its button-up styles have lots of different fits, with the most popular being the cotton styles that look crisp and polished as you go about your day. The cotton also has a natural stretch that reviewers rave breathes and moves well, so it is great for staying comfy.

BR’s designs are trendy and modern classic that usually have an excellent fit for most men.

Untuckit’s shirts are a popular choice if you are looking for performance styles. The Untuckit Performance styles are constructed with a moisture-wicking fabric that is a nylon and lycra blend. It also contains the Untuckit wrinkle-free technology to keep you looking professional and polished throughout your day.

You can get this style in a few different fits, including regular, slim, relaxed, regular tall, and slim tall fit, so there is pretty much a fit for every body type. This lightweight fabric is super soft and easy to wash and dry. Untuckit’s performance shirts are perfect for keeping you cool and dry with no wrinkles.

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 you won’t dread wearing. The fabric is a 65% polyester and 35% cotton blend, and it features a point collar with a regular cuff. It also has a chest pocket, which some men like and some not so much.

This Van Heusen shirt is easy to take care of because you can machine wash it, and it is easy to iron. It 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

If you are serious about finding a comfortable style, you will want to check out some of the start-up brands that are redesigning office wear using materials 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 handy 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 pretty good regardless of their body type, and the fabric drapes well, while the stretch has enough give to make them easy to move in. Its temperature-regulating material also makes this an exceptional all-around travel option since it won’t crease. They come in a slim or a standard fit in sizes XS to XXL in eleven different color options.

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, known for being super comfy and 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.

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 remaining crisp, making them a great professional work option.

One of the Nordstrom brand’s most popular styles is the Trim Fit Non-Iron Dress Shirt. It is 100% cotton and has a straight collar with removable collar stays and adjustable button cuffs.

The Twillory Leader is a super comfy option 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.)

The Leader 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 shirt’s overall luxe feel; also, it doesn’t show the dirt or grime that can sometimes show on collars.

If you want to splurge on a high-end classic brand known to feel great, you may want to check out the Eton Slim Fit Twill 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 worth it.

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 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 wear 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.

Mizzen+Main is one of the few shirt brands 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 have an athletic built frame or 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 versatile since they feel like athletic wear, but you can wear them for work or dress them up for a night out.

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 relaxed 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 long time, and they still make high-quality shirts with 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

The Ludlow is a trendy style that is easy to find at your local J Crew.  It has 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.

Ledbury’s Blue Fine Twill Spread is a style 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.

This Ledbury style’s standout feature is the collar that keeps its shape nicely, even when not wearing a tie. With or without a tie, this is an excellent option for the office.

Brooks Brothers is a dependable classic place to get 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

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 and 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 get 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

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 and offer a discount if you do the multi-buy option. Charles Tyrwhitt’s designs are generally a good comfort option because many 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″. Their regular dress styles 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