My sense is that any cotton that has the fibers of fabric running at some type of bias tend not to wrinkle. So, cotton twill -- all fibers running at a 45* bias -- and herringbones -- fibers running at alternative 45* biases -- will tend to wrinkle the least amount when compared to other cottons of similar weight. Of course, also the thicker the cotton the fewer the wrinkles, but then you start talking about real oxford cloths, etc. I agree with A. Harris about the fit -- I have 2 Jantzen shirts so far. One was a form fit, the other a medium fit. The medium fit wrinkles more than the form. This may have something to do with the fabric, but the fit must have something to do with it as well. Moreover, the form fit is INCREDIBLY easy to iron. I suspect that is the case with most Jantzen fabrics, but it must have something to do with less fabric to iron as well. I currently am waiting on an 11 or 12 shirt order. I copied Bjorn H. in many respects -- I think I ordered 4 fabrics that he has -- because I took him as the gospel in terms of fabric quality. I put in a hefty amount of twills and herringbones (probably at least 6 out of 12), and also did two pin-point oxfords (I've seen some impeccably dressed gentlemen in my office wearing beautiful solid color suits with pin-point oxford shirts and it really is a nice contrast when you have a nice color shirt; I ordered the lavender pin point oxford). I should be receiving the shirts within the next 2 weeks (that will put me at 5 weeks). So, if you can hold on for a bit, I'll give a report. Note that I ordered mainly dress shirts, as opposed to more sport shirts. So my fabrics may not be the ones you are going for anyways. But I did order a purple gingham check (Bjorn H. rec); a multicolor stripe (another Bjorn rec); and a prince of wales green/blue check (my one shirt that will truly be limited to casual wear).