But seriously, I think they fit very different areas in a wardrobe. My Alden Wingtip boots are an overlap in color to a couple different shoes I own, but I don't really think of them as duplicate. I think CXL and chili boots are very different, especially if you shine your chili boots.
One is a totally casual pair that is completely comfortable with jeans or chinos but isn't going to dress slacks or more formal business casual attire. I wear my (natty) CXL boots without too much thought about weather, getting a bit scruffy, etc.,
The other is fine with jeans but really shines with chinos and dressier pants and many suits if you want to go there. I wear my Alden WTB's in lots of ways (I love them with jeans), but I do consider "what am I going to be doing out there?" when I wear them - I wouldn't take them out in the woods, etc. if I had an easy alternative.
As for what people see, I think it is more about you and what you're trying to present. I dress for myself - looking like I want to puts me in a frame of mind. The boots are part of an overall picture and more important as a detail to you than most people. Coco Chanel said something close to this once: "If a woman is poorly dressed, you notice the dress. If she is impeccably dressed, you notice the woman." Same here - little details are meant to disappear IMHO. (And I'm a dude, but whatever - the girls can't have all the fun)
Net: I think there are ample reasons to have both of these boots. They're in the same end of the color spectrum, but have very different roles. My $0.02.
Really appreciate this breakdown. Trying to gather as much insight about brown cxl as I can before September (im a cxl virgin, and this will be my first cxl experience)...this gives me something to chew on...Im thinking that if I just cant get past the perceived redundancy aspect I have with the two, then I may just exchange the dark chili for oxblood, and cop the brown Higgins Mill, and walk away with a win-win.