OK, let me start by saying I'm glad y'all got me off the fence about my boots. With that all sorted, I can now ask for recommendations for work shoes.

I work outdoors (more or less), and I mostly have winter covered. So many options for winter, lots of boots. My Chippewa boots are supportive and comfortable, and they're made to take abuse. I'll probably replace my Bates tactical boots with a wide width pair this winter. I will probably be dropping a couple hundred bucks on them, which hurts but I loved the last ones to death so I'm cool with it. They're made well enough to withstand 3+years of my serious abuse and they're comfortable, so they're worth the price.

That's not real helpful when it's September 15th and we're still seeing temps around 90F. I've managed to get through summer with my Twisted X canvas loafers (they're not real supportive for my arches, but there's room for an insert if they start bothering me too much). See pic 1. While they're not wide width, they're wide enough. No pinched toes, blistered balls of feet, abraded ankles, blistered heels. However, I can't wear the same pair of shoes every day, hence the need for recommendations. My wide width Naturalizer sneakers are comfortable as in no pinching or rubbing or smoothing, but they're not real supportive and there's no cushioning. They'll do for now, but they already look like death because they got wet and wrinkly after 2 wears.

Must have:
* width. Generally, I need a wide width. Some medium width shoes run wide and that's fine.
* leather or easily washed fabric. By wash, I don't necessarily mean washing machine. A good squirt with a water hose or shower wand will usually suffice to get the fruit stickies out. Absolutely no synthetic leather, it's too unforgiving with the comfort and the smells.
* arch support or room for an insert. High arches, and a super picky right foot (old injury).

No high heels, no platforms. The ground where the pumpkins and firewood and watermelons happen is gravel and has lots of wood chips and giant chunks of bark and other hazards for platforms and heels. Lug soles are cool but not a must-have as long as it isn't slippery because the walk-in cooler is often treacherous.
No boots. I wear shorts, and this is Texas where it's freaking hot, so it has to be summer appropriate. No sandals, because that's just asking for miserably sticky feet.

So, any recommendations are very welcome. I have GOT to keep my feet happy, because the last weekend at work was just gross. My right foot, the picky one, hurt all weekend. Today was better with the Skechers, but still not where I know it could be. I'm not averse to spending money on work shoes if they're super comfortable and supportive. It just chapped my hide to have to drop almost eighty bucks on Skechers because I couldn't stand the foot pain and I couldn't wait on shipping and didn't have time to drive down to the metroplex where there's better shopping.
Thank you for your help!
XOXO