I've ordered a whole lot of booties over the past month.

I've made my decisions, but I figured maybe this would be useful for someone?

Brown Lace up Boots
#1-2 are Steve Madden Leader boots in brown. These fulfilled my want for brown mid-calf lace up boots. I also tried the Born Zelia but I didn't order brown and then I didn't get the sale price, and then I didn't want to pay the full price. I also forgot to take a picture. I also liked how the Steve Madden's have a zipper on the side which will make them easier to get on and off. I keep all my shoes by the garage and put them on while carrying bags and toddler chasing, so ease in putting them on is key.

Black Wedge Booties
#3-5 is a comparison between Clarks Rosepoint Dew in black and Toms Desert Bootie in black. I ended up keeping the Clarks, though it was a tough decision. I liked the plaid liner in the Toms, the heel is slightly shorter and a little wider making it feel more stable. The cushioning of the Clarks is better though. My goal is to wear these with tights and dresses/skirts, so I felt the pointier toe on the Clarks was a little cuter for that application. I am tempted to go back for the Toms in a different color though!

Moto Booties
#6-8 is a comparison between Frye Veronica Back Zip Short Bootie and Cole Haan Alix Moto Boot. I already own Frye Veronica slouch boots in brown, so I was a little hesitant to duplicate, even though I really like them. In the end the leather of the Cole Haan was a little softer and they were more comfortable. I felt they were a little more feminine with the blocky heel too. And, they were a bit cheaper. I know the Fryes would have broken in, but they are quite stiff to start and I think that put me off. Plus, the back zip and snaps were kind of a pain compared to the pull on style of the Cole Haan.

#9 is a comparison of my very old (c. 2004??) Via Spiga black wedge booties which I haven't worn in years since they are completely worn out, but saved nonetheless, and my new Clarks. So I'm excited to finally have a replacement this year!

Anyway, hope this was helpful for someone!