As much as I try to avoid it, I occasionally find myself standing in line at Wal-Mart. I don’t have any moral issues with shopping there, I just find the real-world examples of the “benefits” of urban living to be disheartening and anger inducing. There’s a reason peopleofwalmart.com exists and peopleofwhateveruppermiddleclassmallyoucanthinkof.com doesn’t.

This past Monday was one of those days that I found myself waiting in line at Wal-Mart’s customer service counter hoping to make an exchange. Immediately ahead of me were two thugs hoping to return a stolen gifted iPod touch without a receipt. They looked a lot like these two.

During their numerous attempts to initially sweet talk, then intimidate, and finally pout with one rep and a manager, I found myself with plenty of time to sit back and observe the details of what they were wearing.

It was very obvious that these two were concerned with how they looked. Both had on baggy pants that were sitting well below their cheeks. Both were wearing XXL shirts – one was a plain black and the other looked like a black and red Miami Heat jersey. Both had chain necklaces and tattoos on their forearms written in a flowing, old script.

The one wearing the jersey even had on a black and red, flat-brimmed ball cap with the sticker still on it and brand new black and red Nike’s. To cap off his outfit, he had tucked the extra-wide hem of his ridiculously baggy jeans into his ankle monitor – you know, the kind that criminals wear when they’re on house arrest or some other form of probation. At first I thought it might have just gotten caught accidentally, but I looked closer and saw that it had been tucked in about three-quarters of the way around his ankle. There’s no way it was unintentional.

The point of all of this is to illustrate that every man, even the one who takes pride in being beyond the fringes of respectable society, is aware that his clothing communicates a message. These two probably would have called me a fag, bitch, or some other hilariously inept insult had I called them out on it, but that doesn’t mean they put any less effort into finding the right clothes and putting them on each morning.

Any man who still lives under the delusion that his appearance either is or should be irrelevant is fooling himself. Every man cares.

The button-down collar is a classic, Americana-based style that has been used by men for years. It’s a great way to dress down a suit, or dress up a shirt and jeans.

Similar to other styling details like hacking pockets and jacket vents, the button-down collar has its origin rooted in men’s sportswear. More specifically, the button-down collar was invented by Ivy League Polo players as a way to keep their collars from flaring up into their faces during a match. Because of its sporting origination, it is a more casual shirt collar and falls securely in the Play category.

The beauty of a button-down collar is its versatility. It is equally at home on the beach as it is in the office. The soft roll of the collar and the position maintained by the buttons mean it will always stay in place – with or without a tie. This is ideal because other collars have a tendency to either fly away or pancake beneath a jacket lapel.

While you’ll want to avoid them when attending a black-tie gala or when tinkering out in the garage, the button-down collar is at home almost everywhere else. Grab a few, wear them well, and use them to replace the default T-shirt you throw on with your jeans.

On top of fit, there are certain design elements that go into suits and sportcoats that can make them more flattering in different environments and on different body types. One of the key design aspects of a single-breasted jacket is the number of buttons. This can range anywhere from one to six and there are some big differences in how they affect your appearance.

One Button

Because of its uniqueness, a one-button suit finds itself in the extremes of formality. This means you typically only see it on tuxedo jackets or more casual suits and sportcoats. The general appearance given off by a one-button jacket is a modern refinement and this is why it’s best used to either focus on refinement (tuxedo) or modern (casual) when choosing this style.

The shape provided by a one-button jacket is most flattering on slim men. Because there is less room for drape, a large man’s belly can cause the jacket to split – making it look too small.

Two Button

A two-button jacket is the most universally appealing. It is the most timeless of all button configurations and also flatters any body type. A two-button jacket is also appropriate in everything from the most casual sportcoat, to a conservative business suit, to a tuxedo, and anything else you can think of in between.

There are no men who look bad in a two-button suit. The key to fine tuning it is to focus on the button stance. The higher the top button is, the more it visually shortens the torso and lengthens the legs. The opposite effect is created by lowering the button stance. This means men with disproportionate legs or torsos can help even out their proportions by wearing a two button jacket with a button stance that is made specifically for them.

Because of its universal appeal to all body types and all formalities, I recommend a two-button jacket as the best choice for the man who is starting to build is wardrobe. Once the basics have been established he can move on to more unique configurations.

Three Button

The three-button suit is the type that has seen the strongest wax and wane in popularity throughout the decades of the 20th and 21st centuries. As a result, some men will consider it conservative, others will consider it outdated, and then others will see it as fashion forward – meaning that a three-button suit tends to be a statement piece. Because of its fluctuating popularity and its roots in the business world, it is rare to see a three-button tuxedo jacket and inappropriate to wear a three-button jacket as a sportcoat. It is much better worn in environments of a business or conservative nature.

Unlike the two-button jacket, a three-button suit is only appropriate on certain body types. Because the third button rests so high on the chest, the V-shape created by the lapels is shortened, making the torso appear shorter and the shoulders appear less broad. These visual effects mean this style of jacket is best worn by men who are slim and taller than six feet. On men of any other build, a three-button jacket will make them appear short and squat.

Right now three-button jackets are pretty out of favor. I couldn’t even find a flattering image of one that was buttoned up to include.

Three/Two Roll

This is an extremely subtle variation of a three-button jacket. The difference is created when the lapels have a soft roll as opposed to a hard crease. This allows the wearer to button only the middle button – making the jacket appear more like a two-button suit. A three/two-roll jacket has a classic Americana feel to it and should not be considered for tuxedos or other formal jackets. However it is still appropriate in business situations and is awesome on casual suits and sportcoats.

While a three/two-roll jacket does give a similar visual effect as a two-button jacket, I recommend men who are 5’9″ or shorter avoid this jacket. It has less leeway in button configuration, making it still better suited to men of an average height or taller.

Four, Five, and Six Button

Avoid them. While it is true that suits originated from military jackets, and military jackets are made with many more than three buttons, the two worlds are separated enough that suits have their own rules and guidelines. Occasionally you will see fashion-forward men like athletes, celebrities, or designers attempt to make a four-button jacket look stylish, rakish, or daring. They don’t. They look stupid and trendy and make the man wearing them appear as if he’s trying too hard. This may change in the future, but for the last hundred years or so, three has been the maximum number of acceptable buttons.