Knee high boots are the most useful shoe of fall, but only if they fit. A wide calf boot gives you more room in the shaft, so it zips up easily, sits smoothly over your leg and works over jeans or tights. I went deeper on a related idea in Khaite Boots: Shaft Height, Calf Width and Comfort.

 

Every boot here comes in a wide calf fit, and many also come in a regular calf. Check the fit option on the product page before you order.

 

I sorted them into leather riding and block heel boots first, then suede and dressier heeled boots.

A black leather boot with a low block heel is the one to start with. It works with jeans tucked in, a midi skirt or a sweater dress. The black pair with a square toe looks especially modern, and the faux leather pairs are a great lower price option.

 

For brown, the dark brown riding boot with a ring detail and the caramel leather pair look rich next to cream and camel. The light brown western style pair adds a little character, and the black lug sole boot is the one for rainy days.

 

My fitting room test: measure the widest part of your calf and compare it to the shaft width listed on the product page. What I would skip: shafts with no stretch panel if you are between sizes.

Suede knee high boots look softer and more dressed up. The black suede kitten heel and the dark brown flat suede pair are the easiest. The chocolate suede pair with a pointed toe and the one with a block heel look great with a knit dress.

 

For something dressier, the burgundy slouchy pair on a slim heel is the statement here, and the deep brown leather kitten heel feels elegant. The dark brown leather pair and the black suede pair with a block heel are easy picks for work.

 

What I look for: a full length zip. What I would skip: a heel too thin to walk in all day.

Wear black leather boots with a sweater dress and opaque tights, or tuck straight jeans into a brown pair with a chunky knit.

 

Keep a pair of boot shapers inside so the shaft stays upright and does not crease between wears.