A well made pair of leather dress shoes will eventually mold themselves to your feet. It's a different feeling to a sneaker, not fabric and foam rubber obv, but they can be super comfy. I've even got a pair of Frye boots I've had for like 20 years that feel tight when you first pull them on but then they're just like a second skin, you forget they're even there

I wear dress shoes with thick black athletic socks. They feel 1000x better. Who really looks closely at your socks anyway.

Really depends. They've dropped off in quality and there are better shoes, but in terms of pure comfort, Cole Haan uses the same cushioned inserts as Jordans in some of their dress shoes, as one example.

Bad dress shoes feel awful. When I used to wear them at a dresser job, I loved my Bostonians.

I will never understand chunky shoes. When I was young, people at school were picked on for having very big feet, getting called a clown or a t-rex or something.

Now it's fashionable to wear shoes that are both oversized for your feet, heavier than they need to be, and make your feet look disfigured (not that I have anything against people with disfigured feet). What does having weird shapes on your feet achieve? Especially when the same people wear the same bland outfit-of-the-month as all of their fast fashion friends. Either lean into the avant garde or stay basic. You can't pick both and pretend it's cool.

EDIT: Not particularly bashing Elliot here. I don't like the look but at least it's mostly cohesive? And definitely on-brand for Elliot's style.

Same company that sells a canvas tote bag for $1700. Must be legit!