About Boots and Socks

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.

I hope these tips are helpful to you.

  1. Very good advice. It is very difficult for me to find boots the fit well and mainly stick with booties and pants. When I travel north during the winter and boots are required I have had success with Pikolinos ankle boots. They are well constructed and stylish. Amazon carries this line and many times at a good price.

    Thanks Susan

  2. (Breathes a sigh of relief. . . ) . I am so glad I am not the only femme d’un certain age that doesn’t do dresses very much. As much as I would like to wear more dresses, you are so right – our bodies do change even if we are taking care of them. And for the life of me I will never understand why women our age wear a dress with bare legs. Your routine — long pants line or dresses with nude hose/heels — is the same thing I do. Thanks for making me feel normal!

  3. I do not wear tall boots anymore for the same reason as you, Susan. Prior years of working out and weight lifting have left me with very muscular calves and even the wide calf boots don’t fit. So it is short ones for me. I have a favorite pair by Munro Sport but haven’t been able to find the exact style this year. I’ll have to try a different style in the future. My jeans must always come over the top of my boots. I hate seeing someone wear short boots with a couple of inches of exposed leg. Just my pet-peeve.

  4. Your other readers read my mind! I have been wanting to ask you for the same information, but I have been so busy with Christmas preparations that I haven’t gotten around to writing that email. Thank you for this information – it really helps!

  5. After a year of not getting to wear boots because a custom brace was being made and fitted for me and required semi-bulky walking shoes, I am now wearing the most helpful brace *and* boots. It took a double zip wide width boot and a trip to shoe repair to see if they could fix the boot to fit the brace. They could and I and am happy as a clam, wearing boots and feeling cool. Thanks for your post!

    1. Hi Peggy – guess I’m not the only person with a brace/bulky walking shoes who still likes to look my best…isn’t this ‘site informative/interesting/inspirational? I have adapted many of Susan’s looks to my own situation, and you’ve given me a good idea for dealing with boots! Now if I could only erase these 15 pounds I’ve gained since I’ve been married (nearly 48 years!).

  6. I love dresses in the winter with leggings and a riding boot.

    In the winter in the north sheer pantyhose don’t work as well as tights. JJill makes a great one.

    Really like all of your boots except the tack boot. As a rider they should stay in the barn.

    Most comfortable manufacturers of boots: Cole Haan, Born, Ariat

  7. This post was really helpful, as I also am switching from dresses to pants and boots, but finding the sock pairings tricky. I’m confused though–in the beginning, you said you wear tights or sheer hose, but at the end you said you wear nude pantyhose with dresses. So do you mean you wear tights or hose under your pants, and if so, full or knee highs, and how do you keep them from sticking to the pants? (Sorry if I misunderstood and this is a dumb question.) Thanks again for all your observations and advice.

    1. If I do wear a dress, I will always wear silky nude stocking with nude shoes in the warmer weather. In the winter, it will always be black hose and shoes with a black dress. The thickness of the legwear depends on the casual or dressy attire I wear with it. Sheer with dressy items, opaque with more casual items. The opaque tights I have now are from White House|Black Market. They have a smooth, silky texture, so most of my pants do not drag on them. If they do, I take that to mean I need to switch to pantyhose instead. (I don’t wear knee highs.) I hope this helps to clear up your questions. Sorry I wasn’t clear. I started out thinking only of the winter months.

  8. I was wondering what brand/color you use for your summer hose? I’m having a hard time finding something just right. I just can’t do the no stocking thing that the younger gals wear. Mary

    1. I always look for pantyhose that have a bit of shimmer to them and absolutely no orangish hue (remember the horrible orange color called suntan?). I have these at the moment and they are nice looking on the legs while giving some coverage as well.

  9. Very helpful. I love the main photo of you on this post. You look even thinner. Love the
    outfit. Thanks for the information.

  10. I am a little confused. Since you stated in the second paragraph that you don’t wear tall boots because of muscular calves (a problem I share) but are shown with the leggings and tall boots, can I assume that you found a pair that worked and, if so, which ones? Thanks in advance.

  11. Absolutely love the look with the leggings. But, I struggle with appropriate leggings. Where do you find good quality ones that hold up and are heavy enough to wear like you do? Your blog just keeps getting better and better; you look fantastic and you’re an inspiration – keep it up!

    1. I look for the thickest and heaviest leggings I can find. Fabrics such as denim, faux leather, and very heavy knits that are completely opaque are the only ones I consider.

  12. Thank you so much for these very helpful tips about boots, Susan. You mentioned an excellent tip that triggered an “aha!” moment for me: “…the taller the boot, the lower the heel”. Merry Christmas and Happy 2018 to you and Mr. Mickey!

  13. I enjoyed your blog on boots. Have you ever tried cowboy boots? They are awesome and VERY well made for the money. I wear “ropers” during the winter with dress pants, tights, or jeans with socks. I have a pair of black ropers and a pair of brown ropers with pink stitching. I get a lot of compliments on them. They have lug soles that prevent slipping.

    1. I would wear nude hose, but I usually wear nude shoes as well because I don’t want to break up that line to the floor. I always try to make my legs look longer than they are.

  14. Susan,
    Interesting post. You certainly have a wide variety of black boots. My daughters and I were also cursed with stumps for calves and are wondering if the stretchy boots are tolerable for extended periods of time without blood flow restriction? Have you found good brands in other colors, such as cognac? Black is always slimming for the problematic areas, though. Thank you for your continued expertise and entertainment.

  15. Hey Susan, great article. Super fashionable. will definitely introduce my mum to your blog. While I’m not really in favor of the tight toe boxes and high heels on boots, the Chelsea boots you mentioned seem to have a wider toe box and low heel. Which I’m absolutely in favor of if one has to wear heels. My point being building the arches of your feet are of utmost importance when it comes to living a healthier life. Problems in the foot move up the kinetic chain, from the ankles to the knees to the hips and the back. Here’s a great article on building the arches of your feet: https://www.thesewisefeet.com/how-to-fix-flat-feet/

    Hope it helps you and your readers!

    Jason Hughes

  16. Always a pleasure to see your posts
    As glamorous as ever
    I always try to follow your advice and receive many compliments
    Keep up the good work ,!!
    Us older ladies really appreciate your
    help and always nice to see you smiling face

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I share tips and inspiration for using what you already have in contemporary ways. Defining words include effortless, classic, refined, discreet, and elegant. My style is chic, minimal, and timeless with a bit of edge.