Hi Nanabear --
I am also fussy about color combos but I guess I'm fussy in a different way from those who only like cognac and lighter browns with black!
I'd wear your chocolate booties and black jeans together in a heartbeat. I love mixing low-contrast neutrals (navy/denim and black, navy and deep brown, charcoal with either).
While I don't really care if folks think I pulled the wrong color shoes etc to go with my clothing and often wear only solid versions of black/brown together, I *do* think adding a black + deep brown pattern into the stew can make things seem more intentional.
Below are some ways I wear my espresso and black together. I say wear yours in good health!
Photo 1: Black/brown scarf, black leather jacket -- I've worn this with black and dark brown skirts and trousers
Photo 2: Putting a black/brown knit top with solids of the same -- a bit too much leather here given black boots/jacket and dark brown purse!
Photo 3: I've worn this with brown jackets/sweater and boots as well as the black shown here
Photo 4: me holding up the knit top against the scarf to test the mix, so it looks a little lumpy -- I did go onto wear the two together!)
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