I love Sidi quality but their last is too curved for my feet and I get that same pain on that lateral tuberosity, the little wing-ding bone where you show it in red.
So, Specialized last is definitely straighter and I just got Shimano shoes. The last is a bit more curved that Specialized, but straighter than Sidi. Time to try on some other brands.
LOL! The “wing-ding” bone. Pain at the 5th metatarsal head is generally a shoe gear/pressure irritation as was mentioned (esp if you have a mild tailor’s bunion, or lateral bowing of the 5th metatarsal - a common finding that normally isn’t an issue in the general population - just not cyclists in stiff/narrow shoes attached to cleats with 10,000 revs at a time).
As was also mentioned, Sidis generally run narrow (they do make a wide version they call mega) and are awesome shoes if they fit - if not, I’d suggest the Specialized shoes.
Save yourself a lot of time and go try on the new bontrager shoes. I had similar problems, tried the new bonti road it felt awesome. I had LBS order the new Bonti Hilo and it is awesome. Plenty of room in toe box and foot feels flat and powerful where in the sidis felt like foot was leaning to the outside putting pressure exactly where your problem is. Went from road bike to tri bike then got Hilos, i think shoes made more speed improvement then tri bike. Also have never wore socks with hilo. Just did 106 miles(no socks) on sat and not a single pain in feet where before just lived with pain after about 25.
Have had the exact same issue with my Sidi’s and put up with it for 15 years until it really started to become aggravated off the bike. Switched to Specialized trivents and BGs and the discomfort has disappeared.
I had pain a bit back from that area a few years ago, only in my right foot. In my case it was not the shoe but a bad gait; I was running too much on the outside of my foot and not matching my left side’s stride.
I think I’ll try to nab some Specialized shoes on eBay. Are their size scale the same as that of Sidis? If I can currently stick my finger in between my heel and the back of the shoe, should I go down half a size?