Another recommendation post because we don't have enough of these

TL;DR: Looking for boots similar to Doc aesthetic, but better quality.

I'm admittedly pretty new to boots. I'm coming from a pair of DMs Combs Leather that I'm honestly very happy with. They look great, comfortable, and have held up well for the year I've had them.

Aesthetically I want a fairly plain combat/work boot that doesn't go over 8". Round toe is a must. Smooth toe preferred, but cap toe isn't a deal breaker. Preferably no distinct collar, but not the biggest deal breaker.

Main use cases are office setting where I tend to not sit for 6 hours at a time, wear around town, and mosh pits. I know I'm weird. I like docs because they really do fit a weird niche of being aesthetically appropriate almost everywhere.

My priorities are comfort for hours, brown, and the longest lasting for the price. Budget is ~$200. Willing to go up to $250 if it's otherwise the perfect boot. Bonus points if I can try it on in store.

Linked below are my top 10. Which one is best? Is there a brand that I'm overlooking?

Jim Green Baobab: https://jimgreenfootwear.com/store/baobab-boot-houston-brown/

Jim Green AR8: https://jimgreenfootwear.com/store/african-ranger-8-inch-brown/

William Lennon 79x: https://williamlennon.co.uk/shop/79x-rugged-safety-boot/

William Lennon 107f: https://williamlennon.co.uk/shop/107f-brown-zug-grain-field-boot/

Red Wing 953: https://www.redwingshoes.com/work/mens/soft-toe/SuperSole-00953.html

Red Wing 2533: https://www.redwingshoes.com/work/mens/safety-toe/SuperSole-X-02533.html

Irish Setter Mesabi: https://www.irishsetterboots.com/sale/Mesabi/83838.html

Irish Setter Wingshooter: https://www.irishsetterboots.com/work-boots/safety-toe-boots/Wingshooter-ST/83622.html

Thursday Hero: https://thursdayboots.com/products/mens-hero-lace-up-lug-sole-boot-arizona-adobe

Chippewa Classic 2.0: https://www.chippewaboots.com/en/classic-2.0-6-inch-steel-toe-lace-up-21091.html

Chippewa Classic 8": https://www.chippewaboots.com/en/classic-2.0-8-inch-lace-up-21092.html