Can you wear Dansko clogs? I have some in a dark color and in long pants I can get away with those. Great for your feet.

I have not tried the Angela Scott ones -- so pricey! -- but in more my serious running days (and after breaking a small bone in my foot), I wore oxfords from j.crew. It is hard to find lace up oxfords for women, these look comfortable and not too clunky (I like the clunky ones, they just seem more youthful and casual to me). https://www.nordstrom.com/s/trotters-livvy-flat-women/5734717

Angela Scott!

https://theofficeofangelascott.com/collections/womens?gclid=EAIaIQobChMI8JfuzIun-QIVEPrICh1XIgm_EAAYASAAEgKPH_D_BwE

Try Vionic. Maybe something like these?
https://www.vionicshoes.com/willa-slip-on-flat.html?color=187

Why don't you try Naturalizers?

Straight or tapered pants with jodhpur boots, other classic boots, or loafers.

Bump

Also, I have accepted the fact that I’m not going going to win any fashion awards, but my goal is, I look professional, not too dowdy, but I’m not in pain at the end of the day or even after 1 hour of wearing said shoes.

I like booties with a chunky heel. Paige brand has shockingly comfortable ones. I am a runner too and completely get where you’re coming from.

Thanks! I realize I need to move past sneakers/birks at a brokerage firm - at least while I’m new - ha ha. But there are a lot of women who seem to pull off high heels all day - I’m impressed!
I do draw the line at crocs. My teens wear them constantly. I get they’re comfortable but wow they are ugly. I can hardly bring myself to walk the dog in them.

I have the same problem op. I have these and they go with a lot of things.

https://www.dsw.com/en/us/product/naturalizer-vivienne-ballet-flat/482930

I don’t wear standard dress heels anymore, anywhere, but I don’t wear sneakers or Birkenstocks to work either.

Pay for some more comfortable but professional, supportive dress shoes. Loafers, supportive low heels with chunkier bottom heels that are below 1” are fine.

I’ve had good luck with Naturalizer, Frye boots, and things that are rated well for comfort. ( Cole Haan, etc)

Some of the Birkenstock loafers look very professional, I think - are they not suitable for the clientele you work with?

I’m a mid-fifties dedicated morning runner - I to go 4-5 miles most week day mornings.
I struggle with professional shoes. I want to baby my feet, and view moving around throughout the day in comfy flats as a way to stretch my calves out. I don’t take the time to stretch in the morning. During the pandemic when my office was empty and I stopped meeting with clients I completely ditched even my office flats (flimsy, no arch support, rub that wonky bump on my heel) and wore my beloved birks - cute patent leather platforms - I love them. In the winter I wore Sketchers slip ons- basically sneakers. I know - it’s sooo unstylish, but heavenly on my feet.
I am starting a new client facing job in the financial industry. I need new shoes! I tend to wear slacks with a slight flare that look cute with heels - pumps in winter, chunky sandals w a heel in summer. In my mind, I appreciate cute shoes. But I can not fathom wearing heels all day - mostly because my calves get so tight, and it messes with my morning run.
Any recommendations? Signed, You’ll Have to Pry My Birkenstocks Off My Dead Body