Hi Anne! I hear you. I am trying to address the question this year, "Do I have to keep items forever, if they're not obviously and clearly worn out? This is not just a question about preference, since it means I have to find replacements in a challenging retail environment, with less money and time than I've had before.
What about........
A steamer? Yep. It's a purchase, and it's not as fun as lipstick or a new pair of shoes, but I"m looking into it. Most of my items aren't easy to press on a traditional ironing board, and many of the fibers won't take the high heat, either. I wonder if a steam, instead of a press, might be easier on your clothes, and faster, overall? I think it would help with the ruffles --- and the morning rush out the door!
Also, some ideas:
Pairing with a tube or pencil skirt and boots
Wearing open over a white tee, with cropped or ankle pants
Wearing over a dress, or a skirt and top that form a column of color --
Wide leg, flowy pants
The last two would embrace the retro element, since women used to wear ensembles topped with jackets. You could think of the jacket as 40s inspired, rather than 2009 inspired!