How to Buy A Dress Shirt

how to buy a dress shirt
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We admit it: Buying a dress shirt can be intimidating. Mens’ stores can be stuffy. And buying online can be a crapshoot—unless you know exactly what you want. Dress shirts are generally not cheap, either. So you want to be sure you’re getting it right. But how do you know what to look for, especially when buying a dress shirt online?

Men’s Journal is here to help. Here’s How to Buy A Dress Shirt.

#1: Fit

We can’t stress this enough: Fit is your most important consideration when buying any dress clothes, whether it’s shirts and pants or jackets and suits. Even the nicest, most expensive garment in the world is going to appear haphazard if it doesn’t complement your particular physique.

So get sized. By a professional. Whether that means buying a full suit from Macy’s and get it altered on-the-spot (recommended) or just visiting your local shop and getting your body measured, professional tailoring is the only way to guarantee your new dress clothes will look as nicely as you expect. And with the money you’re spending, you should expect your new dress clothes to look amazing and fit perfectly.

mens dress shirts

So get measured, and save your sizes in your phone or elsewhere. Note: If you work out or diet regularly, you may want to get re-measured each time you buy a new dress garment.

#2: Fit

If you’re only shopping for a new dress shirt, however, you can get away with taking your own upper body measurements. (Gentlemen, please: don’t use a metal, construction-style tape measure for this. Borrow your wife or girlfriends’ cloth sewing tape, or buy one at Amazon for a few bucks. Thank you.) Men’s dress shirts are sized using two numbers: your neck size and your sleeve length.

Start by measuring the circumference of your neck. Take the measurement well below the jawline, across your Adam’s apple where the collar of a shirt will sit. Add 1/4″ to that number for breathing room, and round up to the nearest half-inch. This is your neck size, and is the first number you’ll see on a pre-packaged, off-the-rack dress shirt—i.e., “15 1/2 32-33.” Record this number.

That second number is the sleeve length. Measure your sleeve with either arm hanging lightly at your side. Start the tape measure at the base of your neck and measure all the way down the outside of your arm, stopping at the end of your wrist. Round up to the nearest inch. Record this number; it will be the second number in your dress shirt measurement, i.e., “15 1/2 32-33.”

Don’t worry about getting your sleeve length measurement perfect! It’s better to round up. If the sleeves on your new dress shirt end up being too long, you can always get them tailored later. It’s cheap (usually around ten bucks) and any dry cleaner worth their salt will be able to do it for you in a day. That’s why you want to round up.

The two numbers you’ve recorded will be your ready-to-wear shirt size. A well-fitting dress shirt should be roomy, but fitted in the chest and tapered down the torso. Take care that the shirt doesn’t mushroom over your belt line. If your arms bulge through the sleeves a bit, well, good for you! Is your chest stretching the buttons? That’s okay—unless it’s uncomfortable. Feel free to size up a half an inch in the neck next time.

#3: Fit

Didn’t we say fit was important? No matter which style, color, or brand of dress shirt you buy, fit is really the most important factor. Modern dress shirts offer particular cuts, to suit your torso. The average man can’t go wrong with a Classic (aka Standard or Regular) Fit shirt. A Classic Fit dress shirt will be fine for most guys, although skinny or athletic guys might find them too billowy or boxy when tucked in.

Trim or skinny guys should opt for a Slim (or even Extra-slim) Fit shirt. The Slim Fit dress shirt provides a tapered cut through the midsection and waist, with higher armholes and tapered sleeves—but often has little to no room in the upper body.

best dress shirts

If you’re a fit, athletic guy with a defined chest, shoulders, and arms, look for an Athletic Fit shirt. Athletic Fit shirts provide more room in the upper body, with slightly lower arm holes, fuller sleeves, and a severely tailored waist. Some have darts in the back pull the waist section in, to eliminate billowing. This accentuates your back. The Athletic Fit dress shirt is tailored to be snug fitting, and is the best dress shirt to show off the “V” body shape.

Pick A Fabric

With so my styles, it’s hard to know which dress shirt is the right one for you. Most of the terms used to define them are simply descriptions of their fabric and/or weave. Here are a few of the most common:

  • OxfordA simple, sturdy weave (most popular, great for everyday);
  • Pinpoint or Royal OxfordA smoother, lighter oxford (dressier);
  • Poplin—Smooth with a light, loose weave (very casual);
  • HerringboneA textured weave with distinct “V” shapes (very dressy)
  • BroadclothA smooth, tight, high-quality weave (dressy & often expensive);
  • Seersuckerlight, textured, summer-weight cloth (casual and billowy).

Most guys can opt for a typical Oxford or Poplin dress shirt for any occasion year-round, from daily office wear to weddings and other special occasions. If you want to dress it up a bit for a party or interview, opt for a Herringbone—but not in the summer. Whichever you choose, make sure it’s comfortable and fits right.

And here’s a general rule all men should follow: If your dress shirt is tucked in, then you should be wearing an undershirt. Whether you choose v-neck, crew neck, or A-style is up to you. But an undershirt will keep your dress shirt looking and feeling fresher, longer. It will also increase its life span, and help deter ring-around-the-collar. And you never, ever want to be that guy who sweats through his dress shirt. Ever.

Choose Your Collar

Dress shirt collars are a trendy thing for fashion designers to futz with; every few years it seems there’s a new style men are supposed to adhere to. But following fashion is a choice you make, and we’re not here to tell you what’s right for your personal style. The bottom line is to be comfortable and to look sharp.

The Button-down is the most common type of collar. It’s sturdy and versatile, but casual. The rules have become less strict over the years, but in general you don’t want wear a tie with a button-down collar—unless you’re really shooting for that prep-school look. So if you’re going relaxed or business casual, a button-down collar is fine.

Pin and Tab collar shirts are designed to be worn only with ties in extremely dressed-up situations. That said, they look fabulous and signify that you’re a man who gives a damn about his appearance. Pin collars are so named because they’re held together with a collar bar, while tab collars are held down by hidden tabs under the points.

In recent years the Spread collar has been popular among suited men wearing ties. It’s really just a wider Point collar, with the ends pointing outward more than 90 degrees apart. Some guys take the look even further, with the rounded Club collar. The Mandarin (or Band, or Nehru) collar is a short, unfolded standing collar. It’s a bold look that you need confidence to pull off, but you can sure find it in modern dress shirts if you’re feeling like trying something different. 

The Point Collar is the most basic type of turndown shirt collar, as fine for neckties and suits as it is for jeans and boots. It’s been the most common type of dress shirt collar for a hundred years or more because it’s simple and straightforward. And, it’s appropriate no matter which direction fashion is leaning.

best dress shirt

Cuff It Up

There are nearly as many cuff options as collar options, and they all make a statement. Here are a few of the most popular styles.

The Standard, Straight, or Square cuff is the most common type of cuff. It features a single button and a sharp right angle corner. You can also opt for the Two-button style, which allows you to adjust how snug the wrist fits. Two-button cuffs are great for casual situations, because you can leave the second button open for a relaxed look. It can have a square, mitered, or rounded corner.

The Mitered cuff is cut across the corner at 45 degrees and has two buttons. It’s slightly more formal than a standard cuff, adding a touch a glamour and style to any dress shirt. With a Rounded cuff, the outside corner is rounded to a gentle arc. These are great in office situations, where cuff points can become worn from repeated contact with the desk.

French cuffs are the perfect choice to complement a dinner suit. They’re twice the length of a regular cuff, folded in half, then secured with a cufflink. In the office this is likely far too formal a look. But if you’re going fancy, you can’t go wrong here.

There are a ton of other considerations—pockets, back pleats, etc.—but now that we’ve covered the basics for choosing a dress shirt, here’s our choice for the best men’s dress shirt.

The Men’s Journal Pick

With a vast selection of men’s dress shirts, in every color and style from a host of designers and labels, there’s a dress shirt for every man at Macy’s. But if we had to choose one, it would probably be Calvin Klein’s STEEL Non-iron Stretch Performance Dress Shirt. For a winning combination of style, performance, and value, the STEEL line by Calvin Klein is hard to beat.

During the Macy’s Suiting Event, these gorgeous dress shirts, in a wide variety of sizes and five colors, are 30 percent off. Regularly $80, you can get a Calvin Klein STEEL dress shirt through October 7 for just $55.

macys dress shirt

While dress shirts always look snazzy when you first put them on, even the nicest, most expensive dress shirt can be quickly ruined by pit stains. And it can happen fast—especially at work. If stress has you feeling the heat, you need a STEEL dress shirt to keep you looking cool and composed.

The STEEL line by Calvin Klein uses a moisture-wicking, stretch fabric that pulls sweat away from your body for quick-drying comfort. And a slight elastane stretch means they’re perfect for fit and athletic guys. They move with you, instead of fighting your every move. And it never needs ironing, so it’s ready to wear right out of the dryer.

It has a Classic or Regular fit, offering a generous cut throughout the chest and waist with standard armholes and fuller sleeves. So it’s great for most any guy. The point collar goes with most any neckwear and also looks great open, for a more casual look. Best of all, it comes in five colors—pink, white, black, blue, and grey—and in several cuts to fit most any sized guy.

The Calvin Klein STEEL Dress Shirt is available at Macy’s. It’s marked down to $55 through October 7—that’s 30 percent off.

Get It: Save $25 on the Calvin Klein’s STEEL Non-iron Stretch Performance Dress Shirt ($55; was $80) at Macy’s



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