Not an expert by any means, but these are definitely Wagner Ware pans. In the first half of the 20th century, they dominated the market. "Sidney" is for Sidney, Ohio, where the company was based. My wife and I use a Wagner Ware Dutch oven all the time. Great stuff, and yours are obviously in great shape and should serve you well. From what I understand (my wife knows more about this than I do), the vintage pans--which yours obviously are--are prized among collectors. Very cool!
The first skillet is a Crescent foundry (Ozark). There's not a lot of info on when they were in operation. I would guess by the features of the skillet it would be from 1920 to 1940.
The Wagner is an easier one to date. It dates from 1935 to 1959.
Learned an important lesson with cast iron. Made biscuits in the oven in one. They looked beautiful. Put on oven mit to take them out. Holy crap it was like 9000 degrees. Burnt my hand right through the glove. Stung for like an hour. Biscuits were great though.
All I have read with the dates are what I posted. That skillet was made in that style for years. No real way that I know of to tell the date any closer.