Are you looking to get into menswear? Or have you been wearing it for some time, but would like to dive a little deeper? Then pull up a chair, because I’m going to explain a little about shirt terminology, what kind of shirt to wear when, how to find the right shirt fit, and beyond.

First, a little vocabulary.

Button-up (L) vs. button-down (R) / via Uniqlo

Kinda like how all squares are rectangles but not all rectangles are squares, all button-down shirts are button-ups, but not all button-ups are button-downs. A button-up shirt is any shirt that you close with a row of buttons in the front, while a button-down shirt is a button-up specifically with buttons at the end of the collar points that fasten the collar to the body of the shirt. This was designed originally by polo players in England back in the 19th century so that their shirt collars wouldn’t flip up while playing. Because of their origin in sports, button-down shirts are considered informal.

What different kinds of shirts are there, and when is each appropriate?

Below, I’ve ranked four common shirt types from least to most formal. Informal shirts can be worn while hanging out with friends, going to a dance party, cute coffee dates, etc. Formal shirts should be worn to weddings, fancy events, or for more traditional business settings. For the sake of brevity, this guide does not include even more formal options like tuxedo shirts.

The informal work or utility shirt

Via J. Crew

This is the type of shirt I wear most often. It typically has two pockets (often with their own buttons), and is made from thicker, less structured cotton, chambray, denim, or flannel. The collar is soft, not stiff. Sometimes the collar points include buttons, and sometimes the shirt features a chin strap (extra bit of fabric and an extra button at the top of the button placket). This shirt is extremely casual; wear with jeans, cords, shorts, etc. If you want to dress it up with a tie you can, but make sure it’s cotton or linen, as silk should be reserved for formal shirts. You can wear a handkerchief around your neck with one of these shirts, too, leaving the top button unbuttoned.

Examples of this type of shirt: Levi’s Jackson Worker Shirt; Lee Long Sleeve Texture Western Shirt; H&M Flannel Shirt; J. Crew Japanese chambray utility shirt 

The classic button-down shirt

Via J. Crew

I wear this kind of shirt often as well. Usually they have a single pocket on the left with no button, and they commonly have a box pleat in the back. Their collars are soft and unstructured, and the collar tips have holes to be buttoned down to the shirt (keep these buttoned). These shirts are often made from a thicker type of cotton with a weave called Oxford cloth, hence some of these shirts being referred to as “Oxfords.” Wear with jeans, chinos, cords, or shorts; a cotton or wool sweater; or a casual sport jacket or blazer. Don’t wear a button-down like this to anything actually formal, but if you want to, you can dress it up for everyday wear with a cotton or linen tie.

Examples of this type of shirt: J. Crew Secret Wash Shirt; H&M Poplin Shirt; GAP Pattern Oxford Shirt; Uniqlo Slim Fit Oxford Long Sleeve Shirt

The business shirt

Via J. Crew

Business shirts usually do not have a button-down collar, and it’s collar and cuffs are stiffer. They’re usually made from a thinner soft cotton twill or poplin weave, and are often found in blue tones in solid colors or with a subtle pattern. Wear them with dress slacks and a jacket, or dress down a little with chinos. This shirt is medium formality, and can be worn in business settings, or at less formal events. If you’d like to add a tie, silk is a good choice.

Examples of this type of shirt: J. Crew Ludlow Slim-Fit shirt; GAP Zero-Wrinkle Shirt; H&M Premium Cotten Shirt; Uniqlo Easy Care Striped Stretch Slim-Fit Shirt

The dress shirt

Via J. Crew

Dress shirts are the thinnest of the shirts shown here, as they’re made to be worn under a suit jacket. They usually don’t have pockets, and their collars are stiff and sometimes spread wide like the example above, though often dress shirts have a slightly less formal point collar. They may have collar stays, which are plastic or metal pieces inserted into small pockets under each collar point to keep them stiff (remove collar stays while washing and ironing). The cuffs are either buttoned, or have button holes for cufflinks.

This is the most formal shirt listed here, and should be worn with a suit and silk tie to weddings or formal business meetings. If you’re wearing a spread collar, a thicker knot like a Half or Full Windsor fills the space better than a Four in Hand knot (see the differences here).

Examples of this type of shirt: J. Crew Tall Ludlow Spread-Collar Shirt; Brooks Brothers Box Check Non-Iron Dress Shirt; Uniqlo No-Iron Slim-Fit Long-Sleeve Shirt

I can’t remember all that!

It’s cool; just save the below image to your phone, and refer back to it when you go shopping.

How is each kind of shirt styled?

Casual shirts with flat hems are made to be worn untucked, while U-shaped hems should be tucked into your waistband (line up your shirt seam line, and your belt buckle if applicable, with your pants fly). If you’re wearing your shirt unbuttoned over a tee or tank top, leave it untucked; if you’re wearing a blazer, sweater, or vest over your shirt, tuck your shirt in.

If your tie is tied, make sure your top button is also buttoned (you can always loosen your tie and unbutton the top button when it’s time to relax or if you’re out dancing). To roll up your sleeves, unbutton all of your arm buttons and fold each sleeve three times; then, if you want to, you can push the roll up past your elbow. When you’re done, don’t forget to button all the buttons back up again.

As with any rules, feel free to break them once you know them.

What about fit?

A good fit is hard to find! A shirt fits correctly when:

• The shoulder seam lines up with the edge of your shoulders
• The cuff ends at the base of your thumb where your palm begins (so it completely covers your wrist)
• You can fit two fingers between your neck and the collar
• There’s enough room to move around in the body while being snug and not baggy

If you’re a smaller person and men’s small sizes are still too big, try the kids’ section — I’ve helped a few friends find really well fitting shirts in boys size 12, 14, or 16, and (bonus!) they are usually priced a lot lower. Unfortunately for more curvy folks, I think “women’s” shirts often have a better fit around the hips and chest, but it’s hard to find them without darts, pleats, or frills.

I’ve had good luck finding more masculine shirts in the women’s section of J. Crew, and GAP’s “boyfriend” type shirts can be good too. For more formal shirts, Brooks Brothers has great women’s options, some of which are more masculine cut. If you’re looking for a good quality shirt on a budget, check out J. Crew’s sales (and sign up for their email list), or go straight to J. Crew Factory. I usually get my shirts in the $20 to $25 range there.

How do I care for my shirts?

Certain shirts are easier to care for than others. I tend to stick to cotton, since I’m not a fan of the feel of synthetic materials and most “no iron” shirts feel funny to me. I usually wash my Oxford/button-down/work shirts on cold, then hang them to dry (I would not recommend putting any of these types of shirts in a dryer, though I know a lot of folks do). I don’t often iron my shirts because I’m lazy and they’re generally casual enough that it doesn’t really matter, but you should absolutely iron a dress shirt.

If you don’t know how to iron a shirt, check out this video:

Any button-up shirt questions? Post them in the comments!

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