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!
Sartorial infographics are my jam. This is awesome :D
Great info! I’ve changed sizes/shape recently and haven’t tried any button ups on yet, but historically my issues is mostly getting the hips to fit, even in shirts from the women’s section. :/ maybe someday I will find some that fit me!
If the rest of the shirt fits, and you’re feeling brave, you could try widening the hips by opening the bottom few inches of the side seams and sewing little triangles of fabric called gussets into the sides. You can google a tutorial to see how.
I love this post!
Before I ever presented female (or even knew about transitioning), I was a men’s clothing fanatic, and I had a closet full of suits and shirts all tailored and a couple that were bespoke (made to order).
The second saddest day of my fashion life was giving them all to my brother when I transitioned. The third saddest day of my fashion life was taking up a new presentation of skirts (following my mom’s well intentioned but very Southern Baptist guidance). The saddest day of my fashion life was realizing that I could present female and wear my old stuff but it was all gone.
Thankfully, the happiest day of my life was seeing role models in my new environment that showed me that clothing didn’t have to be firmly gender stereotyped, and I’m acquiring new stuff that I like. Thank you for posts like this! Spread the knowledge! XD
This was super helpful! Thanks Cee!
As a lady with a large chest/hips/butt, I’ve always had the best luck with Van Heusen outlets. They make a line of clothing for women that closely follows their men’s lines, but you can only buy it at outlet malls.
Thank you for this very very valuable information. I must find a Van Heusen outlet now.
So glad to help!
this is a Great Article but I am still shook about the button up/button down distinction
Shout out to Cee for keeping us afloat in the wild waters of the web & generally being fantastic.
Thank you :)
YESSS thank you! Especially for the fit guide!
why does this article appear when I have banned myself from buying new clothes?
Thank you, cee! :D
Ok now just show me where to buy a bowtie that doesn’t make me look like a clown!
I love this website so much. <3
Also just here putting in a good word for the nehru collar. Instant style upgrade & looks super sleek under a blazer.
this is a godsend. i definitely like to play around with some of these conventions too!
Love this!
Alright, who else here needs tall sizes? I used to rely on the Gap and Banana Republic for tall sizes, but they discontinued their non-irons (at least in tall sizes, not sure about everyone else) so I’ve branched out to J Crew this winter, and I’ve been pleased. Eddie Bauer does tall sizes too, but not Small Tall, which is what my green bean self usually needs. Any other suggestions?
Thank you, Cee. I always love your articles, I learn so much
Ohhh I love this! Another great store for great button up shirts in my opinion is COS. It’s owned by h&m, but a bit more stylish. Their men’s department is my favorite affordable department ever. They don’t have so many stores in the US (a few in the big cities) but they have a webshop too: https://www.cosstores.com/
I LOVE SHIRTS but I have the worst body type for them. I have wide shoulders and large neck which makes me great for men’s shirts but I have big boobs which means men’s shirts never close properly… (and women’s shirt I can never button all the way up…).
I know, I know, I should get a tailor, but I’ve still not got the money for that :(
also yep, can’t close the last button on a man’s shirt because of hips…
I just wish I could find a company that would care to make shirts for women with large necks!
I’d like to give a shout out to Men’s Wearhouse, whose salespeople always treat me with the utmost respect. They are very good at finding shirts that fit my body.
Oh, and thank you for this informative essay.
I am fascinated and much enlightened by the history/relative formality of the button-down collar!
But can you tell me how to get shirts to stay tucked over my hips? Men’s or women’s, they always come out. Shirt stays tend to ruin the hems…not to mention they are bloody uncomfortable.
I’m new to all of this, but you could try tucking them into your underpants. I did a quick search to see if this would work with button-up shirts as well (re: bulkiness) and found a GQ page condemning the practice as “the quintessence of dorkiness”, which proves this is absolutely something people do successfully. (They also call shirt stays “paramilitary” and wearing them “beyond dorkiness”, so there’s that.)
According to them, “usually [the problem] is caused by (a) their trousers being too low in the rise or (b) their stomachs being too big for their britches”, so you could check for that, but idk, these are cis men, and I can imagine wider hips causing the same issue? To be fair, it’s obviously not very sexy to have someone untuck your shirt from your underpants during a date, but then again, these are cis men, also I don’t plan on wild sex during my workday, so.