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Well then more of an example then, brown tennis shoes goes with just about anything right? Wearing jeans and a grey sweater isn't that crazy is it?

Heel slip will cause blisters on your foot and early wear on the shoe.

would a chambray shirt work with olive green chinos and brown boots?

IMO, the skull one is pretty ugly. Has a huge gold logo all over one side of it

I have neither the patience or the machine/skills, lol

The boot is a Loake Shilton, my sneakers is a pair of chucks.

My brown 1000 Miles just showed up in the mail yesterday. Any quick tips for care? Should I use a tree in them? What other quick product suggestions...

yes i thk it works. but that depends on the tone of the colour
diffcult to tell without pics

Well, if they're non-returnable, I definitely suggest an athletic insole. It'll help with that ankle problem (which doesn't bode well...) and the heel slip. Wear thicker socks too. Both have worked for me. Don't do anything until they're broken in. They're already treated. A shoe tree is to keep the shape of shoes. For casual boots like those, it's a little silly unless you're storing them long-term. Once worn and scuffed, avoid colored polish unless the scuffing is deep and you hate the leather color showing. Use clear/non-colored Kiwi polish for a shine or Mink Oil for a satin sheen, water-proofing and to keep the leather soft. Others might recommend Obenauffs'

Brown tennis shoes? Sounds pretty gross, show a picture.

I litte bit like

White or Black would look 10x better and go with 100x more fits

anyone know how to get rid of some salt damage on leather boots?

Can anyone tell me what is a good way to protect a leather outsole from rain/wet ground?

Does it even need protection (I imagine it does)?

You can still wear leather soles on wet pavement just fine as long as you give them a few days of rest to dry out before you wear them again, but when wet they'll be more susceptible to wear. If you plan on wearing them regularly in wet conditions, I would topy them (a rubber sole placed over the leather).