I LOVE high boots. As a mom, I often feel like I am toeing the line of is this too mommy/is this too over the top and I feel like over the knee boots are my ticket to balancing both in the winter.
I have two go to pairs. One is a pair with a 3" stiletto pair in a dark gray Stuart Weitzman I splurged on around three years ago (this seasons version to the side).
I bought them end of season when Mall of America still had a store (tear) and I will love them forever. I wore them a ton pre-covid with dresses that were not super fitted and over skinny jeans when I was wearing something longer or baggier on the top. For my style, I wouldn't wear them with something super fitted (I'm blushing writing this now :) but I feel killer in them whenever I wear them.
My other pair I adore are also by Stuart Weitzman, their beloved 5050 suede boot. I had a pair of Blondos I used for years (and really did like), but when I saw these at Optiz Outlet last year I think I audibly gasped. I scored them for around $150, which is over $550 off the ticket price! So yes, they are expensive, but they are even more beloved to me than my stiletto pair as they go with everything! Since they have the low heel I can wear them with more fitted and looser items. I wore them to the orchestra with my son pre-covid with a leather skirt and sweater tucked in. I could chase after him still if the occasion arose, while feeling beautiful at the same time. I also wear them a ton for appointments and for just day to day things as they are beyond comfortable with the low heel.
Here's to the real start of MN winter, hope everyone enjoyed our final burst of summer!