Every now and again, we at Esquire like to swing by reddit's notorious male fashion advice subreddit (aka r/mfa) and see what dudes are talking about. Lately there've been a number of urgent inquiries about which and what items and styling options work and do not work, and the questions on the notorious short-sleeved button-up shirt caught our eye. Even though r/mfa is probably going to hate us for it, possibly even kick the author off reddit, and block our lovely Esquire IP address from accessing the site, we're going to tackle this one here.

The short-sleeved button-up shirt is feared by menswear novices and veterans alike, probably because it conjures up images of Apollo-era NASA engineers, which strikes fear into the hearts of many men trying to shed a nerdy past (even though Cold War NASA can be a sick look in its own way, if done right). But the short-sleeve button-up shirt really isn't scary at all, and is indeed a menswear staple that's crucial to many looks, as well as an item that should be in every man's wardrobe.

Still, there are crucial keys to pulling off the short-sleeved button-up. Thankfully these are the same keys to pulling off anything else: fit, color, print, details, and silhouette.

1. Fix the Fit

Even though we subscribe to the notion that most any fit can be pulled off if done properly, that's next-level fashion killer stuff that most dudes aren't ready to hear. The simple answer on fit for short-sleeved shirts is to wear them slim but not tight. Let the seams of the shoulders hit right at or slightly above the point of your shoulder. Make sure you can button the neck comfortably, but that the chest buttons don't pull apart when you move your arms around. And, most-importantly, make sure the sleeves fit close to your arms and don't billow or pop out at an angle.

2. Find Your Color

Color is simple—sort of. If you know what colors look good on you then you should be fine. Bright yellow looks great on darker skin, but will turn a pale person sallow. White and black work well on pretty much everyone, as do navy blue or chambray. If you're not sure about color, ask a salesperson or bring a better-dressed friend. Whatever color you choose for a short-sleeved shirt will also have to harmonize with the rest of your outfit. Again, this is where black and white help. They match everything, as does denim and most shades of khaki. Don't go for more difficult matches like red and purple until you know what you're doing, capisce?

3. Watch Your Prints

Prints can get tricky, and especially so for short-sleeved shirts, as the item's less formal, warm-weather feel invites room for experimentation. If you're just starting out, the easy answer is to avoid prints all together, or stick with something simple, like stripes or plaids. But that's not all that fun. The designer of any good shirt has already made sure that the colors in their prints work together, so if you paid attention to the color step, you should be good here. Print matching is black belt level master of menswear stuff, so there's no need to go on about it here, for now. Just get the right colors for your skin tone, and stick to a plain pants or denim.

4. Sweat the Details

For a less complex item, like a short-sleeved button up, the most important details to pay attention to are all in the collar, and there are three main collar types at play here: the button down collar, the point collar (usually a soft version without collar stays), and the convertible collar.

The button down collar is easiest to wear, and provides the most styling options. If you plan to wear your top button or (gulp) more undone, but don't want to go full convertible (see below), this is your best option. It can also be worn buttoned up, or, in warm weather with a tie and coat (pulling off a short-sleeve shirt and tie with no sport coat over it is so difficult it's barely worth mentioning here. It's possible, but you probably shouldn't even consider it).

The point collar is an awkward one here. It's going to look best with the top button buttoned, as a point collar has a tendency to flop around and splay when worn unbuttoned. Some softer point collars, like what you'll see on a short-sleeved button-up, are made to be worn unbuttoned, but to our eye still usually look sloppy.

The convertible collar—which is what you'll see on an authentic Aloha shirt—is made to be worn unbuttoned, and is the least versatile and least formal of the bunch, usually appearing on a square-hem shirt that's made to be worn un-tucked. But, it's got a great retro look and has been coming back in fashion, showing up on runways and riding the Aloha floral trend back into relevancy (think: Prada, Saint Laurent). A true convertible collar lacks a collar stand (that stiff bit of material that builds a collar up off the neck of a shirt) and should lay wide and flat. Go for this with Hawaiian shirts or other retro-cool square bottom affairs. Wear it to a weekend barbecue, maybe not the office.

Other details you might find on a short-sleeve button-front include pre-cuffed sleeves, which you must avoid, and a variety of pocket styles, all of which are pretty much fine.

5. See the Silhouette

Silhouette is closely related to fit, but is the actual shape of the shirt, and how this shape interlocks with the rest of your outfit. The Aloha shirt, with its boxed fit and square bottom is an obvious example here, and one where you're going to want a slim fit paired with other slimmer items, lest you look like you're wearing you grandmother's muumuu. The easiest way to create a pleasing overall silhouette is to keep your other items, like your trousers, in the same proportion as your shirt, which should make a nice, well-integrated shape.

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Andrew D. Luecke Style Editor, Esquire Digital Before coming to esquire.com, Andrew D.

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