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What to Look for When Buying Men’s Dress Shirts

Ready to step up your wardrobe? We've got everything you need to know about buying quality men's dress shirts.

Advertiser Disclosure: At Slickdeals, we work hard to find the best deals. Some products in our articles are from partners who may provide us with compensation, but this doesn’t change our opinions.

Portrait of a young man shopping for clothes at store

Dress shirts have been the backbone of a man’s wardrobe for centuries. Our fathers, grandfathers and fathers before them owned higher-quality and better-fitting clothing than most men bother to wear today. Many would have likely owned only a few shirts, but had them custom-made. These would last for decades, generally only needing the collars and cuffs replaced from time to time.

Due in no small part to modern society’s continued obsession with hyper-casual clothing (where “comfortable” has become an excuse for “sloppy”), men today do not pay due attention to what was once the primary staple of a man’s wardrobe. This requires correcting.

If you’re OK with buying shirts of the same brand as your olive oil and baby wipes, you might not be ready for this quite yet.

Thankfully, many guys are finally coming around on better style. Popular shows like Mad Men have reminded people that our forebears didn’t do “casual Friday” – they wore suits and dresses to work, they took their appearances seriously, and most importantly, they looked good. The internet has also played a large part in reviving men’s sorely-lacking interest in traditional, quality clothing, giving them unbridled access to information and shirt-makers that they would not have enjoyed even 20 years ago. Now, wearing a full suit to work might be a bit overkill depending on what you do for a living, but a quality dress shirt is never too much.

Your grandfather and great-grandfather didn’t wear cheap, flimsy, polyester “dress shirts.” Their clothes were produced locally, tailored to fit their bodies well, and built to last. If this sounds appealing to you, then this guide will cover the basics of what qualities to look for in a good dress shirt. If you’re OK with buying shirts of the same brand as your olive oil and baby wipes, you might not be ready for this quite yet.

Table of Content

  1. Fits
  2. Fabrics
  3. Colors & Patterns
  4. Collar Shape & Style
  5. Alteration
  6. When & Where to Buy

Fits – Classic, Tailored, Slim

Many style aficionados assert that the most important part of a man’s clothing is fit, and they are largely correct. An inexpensive and lower-quality garment that fits your body well will always look better than an expensive and higher-quality article of clothing that fits poorly.

Generally speaking, a proper dress shirt will be well-fitted to the body without too much excess material. This will create clean lines that are pleasing to the eye and flattering to the body, and won’t lead to unsightly billowing or bunching-up of the shirt fabric. You don’t want a garment that is skin-tight, but too much needless cloth flapping in the wind looks sloppy.

Man wearing a dress shirt and tie

In recent decades, many American brands have tended towards more generous cuts in order to accommodate widening waist lines. Fortunately, shirt-makers have noticed that customers are not happy with this and have started offering slimmer garments. These may be advertised as “slim,” “fitted,” or “tailored” fits. Men with slim or athletic builds should cleave towards these leaner cuts, but be aware: even shirts listed as “slim” may still be cut more generously than a thin guy would like. In these cases, sizes such as “extra slim” might be a better option.

Even for you bigger guys, some slimmer cuts may be worth checking out. Many brands offer several different fits (rather than just regular/slim), ranging from classic generous cuts to a variety of leaner ones. Not all men are built the same, and it’s worth it to take the time to dial in your perfect fit. Even if you are a larger gentleman, a baggy and billowy shirt will look sloppy and will not hide anything.

Another feature to consider is pleats. Pants have them, and so do many dress shirts. These pleats, or folds of fabric, are found on the back of the shirt and are designed to allow extra room in the upper back and shoulders. However, some find that this causes the excess shirt fabric to billow out in the upper back when your arms are at your sides. It’s best to try a few shirts and decide for yourself if you want these back pleats or not.

Fabrics ^

When researching and shopping for dress shirts, you’ll find myriad different fabrics and textile jargon. A rule of thumb: don’t get too caught up in things like yarn number (which only refers to the thickness of the fabric threads, not the thread count) and terms like “ply” (which refers to the number of threads woven together before the fabric itself is made). Generally speaking, higher-quality dress shirts will have a higher yarn number, higher thread count and a softer, smoother fabric. This is well and good, but don’t get too bogged down in all the jargon.

Here is a quick run-down of the most common fabrics used in dress shirts:

Twill: Twill is a soft, thick, diagonally-woven fabric. Twill is best-suited for cooler weather. Herringbone is similar, but has a visually distinctive alternating diagonal weave.

Oxford: Oxford is one of the most common dress shirt fabrics. Oxford cloth is basket-woven, giving it a rougher texture and appearance, which some consider more casual, especially in the case of shirts with button-down collars.Light blue Turnbull & Asser dress shirt

Poplin: Poplin (sometimes referred to as broadcloth) is a thin, breathable fabric that is good for hot weather or for wearing under jackets. Lighter colors may appear slightly transparent, so be aware of this (grey V-neck undershirts are your friend).

End-on-end: End-on-end fabric features a plain, horizontal weave. It is very similar to poplin in terms of softness and breathability, but uses contrasting colors of horizontal and vertical threads to create a more interesting visual texture.

Pinpoint: Pinpoint is technically a type of oxford cloth, but uses a finer yarn making it thinner than oxford. It is thicker than poplin however, so transparency should not be an issue. Pinpoint oxford is comfortable year-round – warm enough for fall and winter, but breathable enough for spring and summer.

For a proper dress shirt, try to avoid synthetic fabrics, such as polyester, at all cost. These are often found on low-end garments and they can make the shirt look flimsy, shiny and cheap. Furthermore, synthetic fabrics do not breathe nearly as well as natural fibers like cotton.

Another thing to consider is “non-iron” dress shirts. These are advertised as eliminating or mitigating wrinkles, and often involve a chemical treatment of the fabric. This treatment can sometimes make the shirt look oddly shiny and can also stifle air-flow, which means you’ll likely be sweating when you wear it. Like Slickdealer Ride_The_Sky mentioned in this thread, it’s best to try on any non-iron dress shirts in-person before you decide if it’s worth it or not. Besides, properly ironing a dress shirt is something every man should be capable of. It’s not difficult and it doesn’t take more than a few minutes. Many people do like non-iron shirts, however, so go for it if you find one that looks and feels nice.

Colors & Patterns ^

If you’re just starting to build a proper wardrobe, solid white and light blue should be the first dress shirt colors to go for; a couple of each should suffice. Once those are covered, you can begin to branch out into other colors and patterns. Pastels like coral or light pink are appropriate for spring and summer. If pink isn’t your style, try a light purple instead. White and light blue are staples, but can get a little boring if that’s all you wear day-in and day-out.

The rule of thumb here is to keep the colors light. The “black shirt and light tie” combo didn’t look good in the early 2000’s and it doesn’t look good now. Keeping your necktie darker than your shirt helps your shirt collar and jacket lapel (if you’re wearing one) frame your face, and draws the viewer’s eye upwards, which is where you want it. A light tie on a dark shirt is distracting, drawing attention down to your bright, high-contrast neck-piece.White and blue dress shirt with purple knit tie

As far as dress shirt patterns, the two basics are stripes and windowpane. Keep in mind that a patterned dress shirt will bring your outfit into casual territory, but is still acceptable for business wear. For striped shirts, make sure the stripes are thin and the pattern subtle – too thick and the shirt will be too loud, making you look like a candy striper.

In terms of stripes, the visual rule is that vertical stripes will make you look taller and thinner, whereas horizontal stripes will make you look wider. Be sure to pick the best pattern to flatter your body type.

Windowpane, which is a criss-cross of thin vertical and horizontal stripes, is a subtle and understated pattern that will almost always be appropriate for the office. Patterns like checks and gingham are decidedly more casual and usually best left to sport shirts. As long as you keep the colors and patterns subtle, however, you can bend these rules a bit.

When wearing a patterned dress shirt, choose your tie carefully. The safest option is a simple solid-colored necktie, as a pattern on the tie will likely clash with the pattern on your shirt and make the ensemble look too busy and distracting. If a solid-color seems too boring, wearing a tie made of knit fabric will add some visual texture and make things more interesting.

Collar Shape & Style ^

One feature that 90 percent of men probably overlook when shopping for dress shirts is collar style. If all you have ever worn is the typical American button-down collar, then you might be one of them. Not all shirt collars are made the same, and certain styles will suit a man better depending on his face shape.

The general rule here is to figure out your face shape and choose the opposite style of dress shirt collar. If you have a thin and narrow face, for instance, you will want to avoid narrow collar cuts and go with something like a wider cutaway collar. If you have a wide face, avoid broad cutaways and go for a narrower style of collar (and a narrower tie to go with it). If you have an average face or are simply not sure what collar is best for you, a subtle semi-spread is always a safe bet.

Dress shirt sizes will include collar sizes as well (such as 15.5, 16, etc.). This number refers to the circumference of your neck. Use a tailor’s tape or even a string to measure your neck. This measurement is important, as proper collar fit will ensure a clean look, as well as comfort while wearing a tie. The collar should leave no gaps between the shirt and your neck, but shouldn’t be so tight that you can’t slip two stacked fingers between the collar and your skin.

One final rule of note is that you should generally avoid button-down collars on a proper dress shirt. These are generally found on oxford cloth shirts and are referred to as “oxford cloth button-downs” or “OCBDs.” These are considered more casual, and are great for sport shirts. However, what you want in a dress shirt is a nice stiff collar that will stay straight and frame your face properly. Many dress shirts will also come with collar stays, which are small pieces of plastic or metal that are inserted behind the collar where it spreads to keep it upright. If your shirt comes with plastic stays (or none at all), buying nicer metal ones can be worth it. You can often find good deals on them (like this one from Amazon with 36 collar stays for $12).

Alteration – Finding a Tailor ^

When first making the plunge into the world of well-made and properly-fitting men’s clothes, it may take awhile for you to dial in that perfect fit. You might find a dress shirt that fits great in the chest and shoulders, but is too wide in the waist, or maybe the sleeves are a bit too long for your arms.Tailor taking shirt measurements

In times like these, a man’s best friend is his tailor. If you don’t have one, now is the time to seek one out. A skilled tailor or alterationist can make all the difference. Every man’s body is different, and unless you are getting every shirt custom-made (which is certainly an option if you have the money), off-the-rack shirts are cut to general measurements and likely won’t be a perfect fit right out of the box.

They may very well fit well enough, and if you’re happy with that, great! If not, then a tailor can tidy up any issues you might have with a dress shirt – and for less money than you think. Standard fees for things like taking in the sides of a shirt or shortening its sleeves usually amounts to $10 to $30 depending on how much needs to be done. If you are ponying up $50 to $100 or more for quality dress shirts that you may wear for years or even decades, it’s easy to see that the added cost of tailoring is worth it to those who want a custom fit.

One final note: when meeting a tailor, be clear about what you want. Even the best tailor is not a mind-reader and many of his clients probably aren’t too fussy about fit, so be sure he understands what you want altered on your dress shirt and what sort of fit you are looking for.

The Bottom Line: Brands, Prices & When to Buy ^

Good value ($30 to $80, made overseas):
Charles Tyrwhitt
Brooks Brothers
J. Crew
Hugh & Crye

High-End ($80 to $120+, made in US/Europe):
Ratio Clothing
Howard Yount
Kent Wang
Todd Snyder

Splurge ($150 to $250+)
Turnbull & Asser

These are just a few of quality shirt makers found on the market today, and their goods (aside from bespoke shirts) can all be had online. Most of these retailers have regular seasonal sales, and some, such as J. Crew, run sales and coupon codes year-round.

Even high-end shirt makers may offer discounts if you purchase multiple shirts, and some tailors offer the same. If going the bespoke route, make sure to ask the tailor if he has any discounts or introductory specials on custom dress shirts for new clients.

As mentioned, most clothing brands run seasonal sales frequently. The best times to look out for deals are around late winter and early spring when stores are trying to sell off their remaining fall/winter stock, and during late summer and early fall when stores are offloading their leftover spring/summer clothes. Signing up for the email lists of your favorite stores is a good way to find out about the biggest sales first. Setting up a Deal Alert is also an option if you want to avoid all the promotional emails and just see the best deals.

See all men’s dress shirt Slickdeals here!

Images courtesy of ©, Hugh & Crye, Charles Tyrwhitt, & Turnbull & Asser.

Our editors strive to ensure that the information in this article is accurate as of the date published, but please keep in mind that offers can change. We encourage you to verify all terms and conditions of any product before you apply.

Lucas Coll

Lucas enjoys reading and writing about men's lifestyle topics such as clothing, accessories, gear, and fitness. Like many men today, Lucas is on a quest to learn as much as he can about the art of traditional menswear and to share that information with others.

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