Autumn boots advice needed

[TheLostSwede]

Hello gentlemen,

I currently have dark brown monk straps and dark brown derbies. I am now looking for a boot and have decided to go for a chukka or a chelsea.
I intend to wear them casual with jeans/cords/chinos and not with suits. I have trouble deciding color and material.

I'm thinking snuff suede chukka

or

black calf chelsea

or

snuff suede chelsea

What do you think looks best? I would like to introduce snuff or black since I already have two dark brown shoes.
Truth be told I want both styles but for this autumn I will settle for one of them.

 

[Murlsquirl]

Snuff suede chukkas. Mine (Alden) get worn all the time.

 

[TheLostSwede]

Snuff chukkas it is

I'll probably get a chelsea next year. Which color looks best on chelseas in your opinion? snuff/brown/black, suede or calf?

 

[Astaroth]

Black calf is almost without exception too formal to wear well with jeans, even in boot form, and so given your list of trousers I'd avoid that option.

I'd more likely go for a dark brown, rather than snuff, in either calf or suede for the 2nd pair of boots. You could consider black suede if you really are wanting to go for black but personally it'd be lower down on my list.

Personally going for an antique/dark tan brouge derby boot this year as my third pair having already got the snuff suede chukka and dark brown waxed calf chelsea