The gray/white/camel colors go with almost everything. It's the style that makes the outfit seem too matchy. It's almost like I have to deliberately mismatch it to make it seem like I'm not trying too hard. When I look at it, I see the straight line which makes me want to pair it with something modern. I also want it to pop, which means I need to go monochromatic or very simple.
I had planned to wear it with a white top and navy pants. I just realized that the white top is too white so I swapped it out for the cognac penny.
The chambray goes amazing with a burgundy top and light taupe skirt. And almost everything else. White jeans, dark jeans, military green, khaki, ....
Now if you wear a lot of black, the colorblock could be great. I am drawn to light neutrals and prints this summer, but the colorblock would look great with my black trench. Chambray might be a little dull with an all black outfit. I don't wear all black much.
I love how you explained about being too matchy and trying so hard to make it look like you're not! I wear lots of dark jeans, white jeans and black jeans with white Ts and light neutrals tops, but not all black. I can see how I must look so matchy matchy to others!
