Good shirts form the backbone of any tailored wardrobe. We recommend getting most of your shirts in whites and light blues (although I heavily lean towards light blues, as white can sometimes look a bit formal). Whether in solid colors or stripes, a white or light blue shirt can serve as a background to your necktie and jacket, allowing you to pick what you want to wear in the morning without requiring too much thought (busy tie, blank shirt).
At the same time, it can be good to have a few unusual shirts in your closet, if for no other reason than to have some variety. In the fall, I like to wear tartans and brushed cotton plaids with corduroy and tweed jackets. They have the kind of visual heft that goes well with a heavier jacket, in a way that a standard, light-blue dress shirt just doesn’t bring. I don’t wear them with neckties (darker shirts don’t really work with neckwear), but they’re great for a casual, open-collared kind of look.
For summer, there are the unusual stripes and checks you see above. Whether in red double-stripe or a summery check, or maybe even a candy stripe that involves three colors, these can be great for wear under casual sport coats. The key is to choose a jacket that leans a bit more on the casual side – something like a French blue jacket rather than your usual navy blazer.
Of course, the problem with straying too far from your usual whites and light blues is that you can easily get into some ugly designs. Try something that’s just a small play off the usual classics and don’t wear these with neckwear. With the right choices, you can add some nice variety to your wardrobe without taking too many risks.