Irregular Choice (IC) shoes are difficult to give advice on because of the HUGE variation in shapes and styles they offer (everything from brogues to heels to sneakers to boots!). The following advice is general only. Always use the AU size conversion if you are comparing to HCD sizing, as the size charts are NOT the same: for example a 38 in HCD is an AU 8-8.5, where an IC 38 is an AU 7.
I would class IC as a medium to somewhat wide fitting shoe – but only in the rounded or more square-toe styles. Tapered toe styles are fine for medium to wide feet, but the pointed toe styles are best for people with more narrow feet.
If you already own Chocolaticas, my recommendation is this: if your Chocs are a perfect to snug fit and/or if you have quite wide feet, you will want to size UP in Irregular Choice. If your Chocs are a roomy or loose fit, you will likely want the same size in Irregular Choice.
“Will they stretch?” Not really.
Orthotic friendly? This will depend very largely on the style IC shoe you are ordering and we would recommend buying a size up if you want to fit a full length orthotic in any of the IC heels.
Wide Foot Friendly? Yes, especially if you follow the advice above and size up.