More questions came from readers asking for tips on wearing boots and socks or hosiery. Today I will share some styles of boots and explain what to wear them with and why.
My favorite boots are low and black. I have a few pairs that I wear in regular rotation all winter. I wear black opaque tights when the weather is freezing, sheer black hose when I dress more formally, and crew socks when I am dressed casually in jeans.
The color of your socks or tights should relate to your pants, not your shoes. Crew socks are shorter than knee socks. I don’t wear knee socks, trouser socks, or tall boots because I have muscular calves. The socks’ top line always shows through the pants, and the boots will not go on over my calves. So there is a physical reason for my choices. My favorite socks of all time are no-show socks here.
My favorite shoes or boots have a pointed toe and a block heel. I never find totally flat shoes with very little structure or support comfortable. I bought the boots shown above earlier this year, and I have worn them more than any of my others because they hit the sweet spot of style and comfort for me. They have been worth the investment.
The boots above are Chelsea boots. The rounded toe has a more casual attitude. My Franco Sarto boots are several years old. I have worn them many times over the years because they are so comfortable and look great with jeans. I prefer to wear a straight leg jean that covers the top of the boot. I do not tuck my pants into short boots or cuff them above the top of the boots because I need to extend my leg’s line as much as possible.
I don’t own any tall boots, but they can be worn with pants or a skirt and black tights or with leggings and a long sweater. Tip for wearing tall leather boots with pants, tuck your pants into crew socks and then pull the boots on. Your pants should always fit very slim to the body if you tuck them into boots. If you wear a leather skirt, do not pair it with high leather boots. That’s just too much leather in one look, and it results in visual overload.
Over the knee boots can be worn with leggings and long tunics that cover your bottom completely. I follow the rule, the higher the boot, the lower the heel. These Vince Camuto boots I am wearing above are from a few years ago. They have a wide elastic panel down the back of them and flat heels.
I do not bare my legs in shorts or knee-length dresses. Things change as we age, and legs are certainly no exception. I am not a fan of wearing dresses, but if I must, I always wear sheer nude pantyhose, and I match my shoes to my skin color in summer. If I wear a dress in winter, it will always be a dark color and worn with black hose or tights and black shoes or boots.