Depends what you want and what sort of things you're walking on, what sort of distance, etc...
Don't be afraid to splash out on quality footwear though, it can be the difference between your feet feeling great or feeling like you can't walk by the end of the week.
Besides that, the only real things I can say are:
I've got a pair of magnum boots for work, they're absolutely solid. Pretty important considering that I'm on my feet pretty much 10 hours straight most days. Only time they ever feel uncomfortable is when the insoles are due a change, or if I'm not wearing appropriate socks for the temperature. Solid all-year-round boots imo, I've worn them in winters and during heatwaves. They help to keep your feet warm (though the cold soon starts to creep in) and they don't feel unbearable in direct sunlight in the height of summer. Break-in was basically nothing. I've had a few pairs and I've never felt like they've been a pain to break-in. They've generally been ready pretty much from the start. So if you're not opposed to a proper boot, they could be worth looking into.
Look at heel lock lacing to reduce heel slippage
In cold weather, the feet are often neglected when it comes to layering up. Be sure to wear weather-appropriate socks as cold feet can make a HUGE difference to comfort. Dunno if I have weird feet, but when my feet are cold, it's not the cold I feel, it's the aches that the cold causes to my feet.