I like both options but see them as serving slightly different purposes.
I am always trying to "lighten up" in winter. It's tough in my climate.
I think the Chie booties are dressier and more feminine/ even bombshell and would work well with dresses and skirts as well as pants. They would blend easily with other prints, IMO. I have several pairs of animal print footwear (one leopard and one snakeskin) and I find they harmonize surprisingly well with almost everything. Maybe not plaid pants, but otherwise, it's pretty easy.
The J. Crew ones are gorgeous, too. They seem more like a trouser boot to me although they might also work with skirts and dresses.
With fair hair, I love having a lighter bootie option for winter. It's great for bookending with my hair and allowing me to wear lighter toppers/ jackets. But in my climate I still find it pretty tough to wear light footwear in true winter. Keep in mind that I am almost always walking, in a very slushy, snowy, grubby city with uneven sidewalks. From late December through to April, it's pretty much snow boots when I am outdoors.
