In the world of tailored clothing, checks can be worn in many ways, but the choice depends on your personality and how much you like loud, bold patterns in your wardrobe.
Checked shirts are usually a safe choice. If you want something restrained that’ll easily pair with a tie, a standard single-color graph check is a good option. Even safer is a mini or micro-check, in essence, a gingham but on a very small scale that reads as a solid from a distance. Moving toward smart casual or business casual, try a tattersall with a tie. For totally casual, tieless looks, choose ginghams and Madras in warm weather and flannel tartans for winter.
On the other hand, if you want to forget about playing it safe, go for a checked shirt with a checked jacket over it to repeat the pattern. Consider how prominent the pattern of your shirt is when choosing a tie. Solid color ties are a safe choice, but you could also try a tie that has a similar repeating pattern on a different scale (larger or smaller circles or squares, for example).
Whatever you choose, one thing you will notice with a checked jacket is how it creates the impression of a wider chest. Tailored menswear has always sought to broaden the shoulders and chest through tricks of lapel width and style and shoulder padding among other things; horizontal lines across the chest created by checks draws the gaze outward to the same effect.
As a general practice, pair your patterned jacket with solid trousers to avoid clashing patterns. Regarding your choice of tie, you can follow two options of layering and either wear a solid tie or go pattern-on-pattern, which requires more skill.
Because they are strong patterns, any check can become bold if it is used on a two-piece let alone a three-piece suit, with the exception of something like a brown tweed glen check. A windowpane suit, even if the lines are muted, always remains assertive simply because the boxes are large and multiplied over your entire body. Therefore, their acceptability depends on the dress code of your office and how much you want to be noticed. Plaid suits are particularly risky as the loud pattern can easily make you look clownish. Italian style tends to be bolder in making use of plaid suits, especially ones with regularly spaced patterns, but they are still difficult to carry off.
It is said that things you can’t get away with in a jacket, like large peak lapels and aggressive textures, are acceptable with an overcoat. The same goes for checks. Though always a statement, a well-made checked overcoat worn with an otherwise reserved outfit is likely to garner more style compliments as a distinctive feature than other garments that would be considered loud.
Checked, typically plaid, trousers appear loud even if your upper body is clad in a solid jacket. Thus, these would best be characterized as a type of “go-to-hell pants” and worn in the same way, as a statement.
A great option for wearing checks in tailoring is a waistcoat. The waistcoat has traditionally been a means of introducing bold color or pattern, adding personality and a sense of fun under a staid solid suit. Whereas bold pants are an in-your-face defiance of convention, bold waistcoats are almost expected, and you can match a color in the pattern with that of your jacket.
As is usually the case with any bold colors or patterns, accessories are a good place to start with checks because they represent a relatively small dose of the pattern and can integrate that bit of interest you want against an otherwise reserved outfit without becoming visually overwhelming. The most commonly represented checks on neckties are windowpanes, shepherd checks, and glen checks/Prince of Wales patterns. Tartans like black are great for casual or wooly winter ties. Notice that when windowpane check appears on a tie, the pattern is displayed on a bias or diagonally to follow the angle of the tip.
In drab winter weather, plaid scarves are a terrific option as well, lending interest and excitement when colors are more muted.