More than any other article of clothing, I have received requests to do a post about sunglasses. Shades are like shoes in that they can make or break an ensemble that has already been put together well.

The first rule is to ditch any sports glasses unless you’re actually playing a sport that requires them. Oakleys, Dragons, those awesome wrap around shades from the 80′s, ditch them all. Basic rule is if you don’t have to wear workout gear, you shouldn’t be wearing sports glasses. Here’s an example of me from 2007 showing you what not to wear.

On top of avoiding sports glasses, you will need to find a pair of classic shades that will fit your face properly. If you have a long face and wear glasses that are too small it will just make your face look even longer. Same reason why men with extremely round faces shouldn’t wear round sunglasses.

Here’s a breakdown of what you should wear according to your face type. Oh, and much thanks (again) to Bronan for doing all the art work for me.

Square

If you’re a man who has a face that looks like it was cut from stone, broad forehead, hard lines, and a strong jaw. You’re a lucky man. You will also want to help take some of the edge off the angles of your face by wearing glasses that are ovular or round. It will help smooth things out while still drawing the proper attention to your strong jaw by providing some contrast.

Oblong

An oblong face is one that is significantly longer than it is wide. It also tends to have a smaller forehead and a weaker jaw. The best glasses to wear with this type of facial structure are those that will add some width and angles to your face. Look for glasses that have more angular lenses and a pair that is wider than it is deep. The contrast will help decrease the visual length of your face and give you some sharper angles.

Round

If you have fuller cheeks, a weak jaw line, or just an overall round facial structure you will want to find some glasses with a bit of an angle to them. The geometry of the glasses will contrast with your face and help frame you better. You will also want to find some shades that are deeper than they are wide. Classic aviators and tear-drop aviators will be what looks best on you. The smaller, metallic frames, will make the angles and the size of lenses more pronounced and thereby increase the contrast with your face.

Diamond

If your face has a weak chin and forehead but strong and pronounced cheek bones you will want ovular lenses and thicker frames to help provide some contrast.  Classics like wayfarers will give you the shape and the frame size you want to help give more visual weight both above and beneath your cheek bones.

Triangular

A strong jaw with narrower eyes or a smaller forehead will give your face a triangular shape. The best glasses for this facial type are those that have heavy frames at the top and are left open at the bottom. This will help add more weight to your brows and forehead thereby balancing out the top half of your face with the lower half. Clubmasters are great glasses to work with this face type.

Oval

If all aspects of your face are proportional it will end up making an oval shape. This is symmetrically ideal and means men with this shape can wear almost any type of glasses they want. The key here is to avoid any extremes in size or shape.

When you’re trying your glasses on, make sure they stay on your face without pulling at the temples. If the ear arms should go straight back and shouldn’t be strained. You should also feel an even distribution of weight between your ears and your nose. One of the biggest differences between an investment in quality sunglasses and buying a pair from the kiosk is how well they fit. A proper pair of   can be kept on all day without your face getting tired, but those cheap sunglasses will have to be worn in rotations.

The last general rule you’ll need to follow is to avoid extremes in colors. The white sunglasses I have on in the picture above were pretty sweet when I was 22 but they look stupid now. I’m sure to someone in their 30′s I looked stupid at the time as well. You will want to stick with colors that flatter your face and work with the overall color of whatever it is you’re wearing. Basically I have three recommendations – black, metallic (like gold or silver), and tortoise-shell. Black is good and universal but it will only really look good on you if you have  a start contrast and tend to wear colors that will work with black shades. If you wear metallic glasses like aviators you want to make sure the metals match up with everything else you have on. Gold belt buckle, tie bar, and watch will call for gold sunglasses, etc. Tortoise shell is the most universally flattering way to go for glasses. It has the heritage of a long tradition while still being current. It will look good with a black suit, or a grey one, or one that’s olive-green, or a khaki linen suit, or… you get the idea.

Sunglasses, like anything else, will require a decision about how much you want to spend. I personally go the route of having one pair of quality glasses that I take care of and then one or two of throw-aways that get worn on motorcycle rides, hikes, and other situations where there’s a higher likelihood of their being lost or ruined.

PS. The month is more than halfway over so take advantage of the reduced price on Basic Consultations before they go back up.