Insoles are the key as recommended by u/Username-Creative.
I recommend having a boot with over an 8-inch heal, as it offers more support for your ankles.
I'm not much of a fan for having a steel toe. It could get you into some legal trouble, should you ever kick someone.
I also recommend getting a boot that feels like a tennis shoe but also will have good traction. My recommendation would be this: https://www.amazon.com/dp/B001HPOGQ6 It has a huge amount of absorption, yet the grip/traction will be good for all kinds of weather.
You might also want to look into getting custom insoles made by podiatrist. They cost me $400 over 15 years ago, but they have lasted me for years! Well worth the investment. Everyone's foot is drastically different, and a majority of the time its not just eh shoe that counts.
Well, like many have said, you're gonna want a black dress shoe, and a simple sneaker.
For the third shoe, I like ~this~ because IMHO it can basically cover everything else in between. It's waterproof and will make it through intense rain/snow, but it's not big fat and clunky, so it actually looks nice and crisp with jeans and a sweater or button-down, and it's comfy in nice weather too. Pick your favorite color.
Timberland Earthkeepers Tremont size 9.5, black - $75 + shipping
These are brand new, never worn. Here's the Amazon page for reviews: http://www.amazon.com/Timberland-Mens-Tremont-Inch-Boot/dp/B00B9PADZ2
Timberland Earthkeepers Tremont size 9.5, black - $75 + shipping
These are brand new, never worn. Here's the Amazon page for reviews: http://www.amazon.com/Timberland-Mens-Tremont-Inch-Boot/dp/B00B9PADZ2
I wear these on rainy days: http://www.amazon.com/Timberland-Mens-Earthkeepers-Britton-Hill/dp/B00NEZ7CWW
The new models seemed to have changed the styling to something I don't really like. There might be some of the older models in your size, like the ones I linked.
I think the 8119 is much better looking than the Brooks Brothers version. That's what I'd probably go for if I were in the market.
They look a lot like Earthkeepers. Possibly an older version or they just got the top 3 eyelets replaced with speed hooks.