Well, it will depend on how much wear you'll get out of them, and only you can know that. But since you said that you wear a lot of black and brown, then a bootie in each color makes sense.

If the boot is great and you can afford it, I think the law of duplicates falls here. I am hard on shoes and have fussy feet. A good looking comfortable shoe is really hard to find. I would get both. I also think there are color combos that will work with one and not the other. Is the brown a lighter shade? That might make a difference.

Hmmm. How have you worn duplicates in the past?

Well I guess I don't understand the question Angie

I like uniforms if that is what you mean. In fact your flop proof outfits are so helpful.

I like classic and fool proof.

Well, I can say that last fall/winter I lived in two pairs of black ankle boots: one black and one brown. They weren't identicals, but this is what I fell back on repeteadly during the colder months when I needed socks and couldn't wear pumps or ballet flats.

The black pair aren't even real leather - they are pleather - but uber comfy and the pleather is actually a plus in our harsh winters. Doesn't get destroyed by salt crystals. I've had them for a few years.

This season I've upgraded to the stuart weisman oxfords - and they are actually a dark silver, not black.

But I'm sure I'll still get a lot of wear out of the brown ankle booties (they're a dark chocolate brown with suede detailing) because they work better when I'm wearing browns and greens.

I always like to have brown and black options in footwear I use a lot because often different outfits just call for one colour and not the other. For me, it would depend on your other footwear and if you have something to fill the brown gap if you don't keep those ones.