Hi, long time since I've been here but...
A problem with finding comfortable shoes is one thing I can relate to...and how!!
The only ones I wear these days (until my daughter's wedding, where it'll have to be sandals) are Hush Puppies Bounce tie-up shoes. Definitely old-lady looking, but the black don't seem quite as much that way.
You'd think if you're not going for fashion it would at least be easier to find something, but we all know that's not true. I had a terrible time getting the right size from Foot Smart, even though I've been wearing the same shoe style for decades. I kept trying to explain to them that what the online site calls "Wide" now actually shows up at my door labelled "Medium" (sigh)...and is indeed a medium. It happened repeatedly. Finally they told me they were no longer available and I found them on the Hush Puppies site. I paid about
$100, and alternate between 2 identical pairs.
Ah, the days when we could skip out of the house in whatever pretty little nothing shoe we wanted! Actually, though, I've had to hunt for a good fit since I was about
25 because my feet have always been wide at the toes. Over the years they've gotten more and more sensitive, and now after 2 spine surgeries they just never shut up - cramping, burning, buzzing, and if I poke them wrong as I'm sliding them on with my reacher and shoe horn - - PAIN!