this post was submitted on 04 Jul 2026
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"dress shoes" feel awful.
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.
Reminds me of another thing I hate about dressing up. I once was chided heartily for wearing the "wrong" color of socks to a wedding. Why would anyone else give a shit that my socks were white instead of black? Apparently they do, and harshly judge me for it.
OK, white socks with a dark coloured suit would look rather silly.
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.
They're owned by Nike
Ha ha, my residual /r/MaleFashionAdvice instincts kicked in on this one.
:)
That's where I got my start! Those heady days of yore. I miss having money.
Bad dress shoes feel awful. When I used to wear them at a dresser job, I loved my Bostonians.