I am also a 44 and made a switch to the s works shoe. I started with the sidi ergo 2, then went to shimano R220's and then the s works. The S works has been the most comfortable BY FAR for ME. has a nice size toe box and the ability to tighten down the shoe with the boa straps is very nice. The sidi ergo had a very nice heel adjustment and super light. the shimano was the heaviest but was also comfortable. (I just go them to small) The shimano was a wider than my sidi's. Looks are all a matter of personal choice but I think the shimano's are the cats MEEEEOW all around for comfort and looks.

helmets: get someone who works a shop to help you. hopefully they know a thing or two and aren't just there for a paycheck and work their shift. My bike shop has a lot of knowledge and took the time to show me the difference between helmet fit. there is a difference between them. some protect the front or back of your head better then the next you try on. after trying them on have the salesman look to see which helmet will have the best coverage of protection.