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I am prone to blisters, and for me, the solution is always wearing some form of socks, unless I am wearing sandals. I find boots or booties are the least likely to give me blisters, because they don't have an edge, and they are less likely to shift.

If they can be open toe, the Dansko Isabel sandal is THE most comfortable work shoe I've ever owned. They have adjustable straps and has a low supportive sole that's a lot like a tennis shoe in terms of feel but they don't look terrible on the foot (they look 100x better in person). I got them for my first pregnancy and they have lasted for years of almost constant wear and have been adjusted through feet swelling. It's actually a discontinued style so you can find it pretty cheap on EBay or other online sources. I buy one size up in Danskos because my feet are wider.

They are more than you want to spend, but I wear my Dansko Maria boots daily. I'm saving up for a second pair in another color. Hands down, the most comfortable pair of shoes I own.

Do you have a comfort shoe store near you? I'd really suggest going there and seeing what is available.

Taryn Rose is a great brand, as is Orthaheel (Orthoheel?). I wear Rockports, especially their boots.

I have feet that are "difficult" (small, wide, bunions) and a long walking commute (1.5 miles each day) so I am very serious about my shoes. Like you, I like in Birks all summer and I love them. I have a pretty casual workplace, so not sure if any of these would work for you, but in colder weather I alternate between: Merrell boots, Toms avalons, various sneakers (right now a wide width Nike), Dankso clogs (I have the Ingrid style), and in the winter I swear by Ugg Adirondack. Most of these are pretty expensive but it is worth it to me, and some of them have lasted forever (my Danskos are almost 10 years old). Agree with others that I'd visit a "comfort shoe" store and try on a bunch of styles. Btw, I used to wear flats all the time but I really can't do it now that I'm older and walk more.