Some thoughts..... Are the shirts 100% cotton? Blends sometimes are not good, and look tired to begin with. -Are you using an iron that is too hot? (if so, lower temp) -Are you 'misting' the shirts as you iron? (if not, do) I hope also that you are removing the collar stays before ironing (if possible) Also, Iron the collar flat out. do not fold the collar and iron in the fold. you want the collar to 'roll' over, when the ironing is done. I concur with the others, and yourself, about getting perhaps some metal stays, or even doubling up on the stays. Try to prepare a weeks worth of shirts in advance, so day to day, you will not have to fuss as you rush off to work. If this problem persists, maybe you better invest in better quality shirts after all. Try Hathaway. They are reasonable quality for the price. One last thought.... A little trick I do, is to take a sheet of papaer towel, fold length-wise twice, creating a strip of paper towel. I slip this between my neck & shirt collar, juuust under the collar line. The paper towel will secretly absorb perspiration, leaving your shirt collar looking fresher longer. -hope this helps.