The materials are far more expensive for starters. They also use more expensive buttons, more stitching at the seams (SC uses 3 rows for example), the dye can often be quite a bit more expensive (SC uses natural indigo in some shirts as an example), some shirts have reinforced parts, the design most likely took much longer to produce (adding to cost), and also brands like Old Navy and Gap have factories which are significantly cheaper, in China, where as Japanese companies make all their stuff in Japan where labor cost is much higher. Lastly, when you only make say 120 shirts in one style you have to have a higher mark up than if you produce 10,000 shirts. If brands like Sugarcane and the Flathead made as little per piece as Gap they would be out of business, plain and simple. Edit: And let me add, if you were to handle a Sugarcane shirt and a Gap shirt beside each other, you would notice huge differences in quality, even if you have no experience in judging it. The SC shirt I bought is probably the single most durable shirt I've ever handled anywhere, let alone owned myself.