How to Wear Boots With Jeans

Woman wearing Llynda More black tapered heel boots with jeans.

Boots and Jeans Are a Year Round Style

Hello lovely ladies! As the designer of ladies fashion boots, I’ve been asked several times, “How should I wear boots with jeans?” Today let’s discuss a few ways we can pair boots and jeans together to help us look amazing, and of course when we look amazing…how do we feel? Amazing!

There are many different cuts of jeans, each requiring a specific style boot to look flattering on the body. For now, let’s focus on how to wear boots with skinny jeans and leggings, as they are women’s leg coverings of choice due to their comfort and slenderizing effect.

One of the wonderful things about skinny jeans and leggings is that they stretch and bend when we do. Women today demand more comfort in the fashion world than used to put up with in the old days. Modern women can be active, fashionable and comfortable all at the same time. And, of course, because skinny jeans and leggings cling to the shape of our thighs and calves, they allow a boot to fit smoothly and comfortably over the top of them without material bunching up under the boots. It’s no wonder that skinny jeans and leggings are so popular with women, especially when wearing boots.

Llynda More grey chunky heel boots with grey diamond boot tops shown in two different configurations with jeans.
Grey ‘More Light’ boots with
‘Grey Diamond’ boot tops by Llynda More

One of the best ways to wear boots with leggings if you want a long, lean look is to wear black leggings with a heeled knee high boot that is form fitting to your calf. In the past, many women have had a hard time finding a knee high boot that fits their calf well because conventional one-piece knee high boots can only be purchased based on a woman’s foot size, no matter the shape of her calves. A woman may have a small foot and large calf, so a size 6 boot may fit her foot, but the upper part of the boot is too small for her calf, or…she may have a large foot and a small calf, again, being faced with the same problem. I designed and patented a boot that comes in two parts for the specific reason of solving this problem. With my design, an ankle boot can be purchased in a woman’s foot size and a matching boot top can be purchased in a woman’s calf circumference size. This enables a woman to get the perfect fit for both her foot and calf. As shown in the photo above in which I am wearing a grey faux leather boot top pulled all the way up to my knee on my crossed over leg, you can see that it fits my calf perfectly. This form fitting boot top coupled with a matching grey ankle boot with a 3 inch chunky heel creates a sleek, long look.

The second way to couple a boot with leggings (or bare legs or nylon stockings) to create a slenderizing effect is by wearing a short or mid-calf boot that is at some point wider than the calf. This creates an optical illusion of the calf being slimmer than it actually is because the human eye perceives width by comparison to other nearby objects in view, in this case a wider boot. With reversible, flexible boot tops that are part of my two-part boot design, a woman can fold over the top of her boot top to create a mid-calf style boot and make a wide cuff at the bottom to give this optical illusion. As shown in the photo above of my boot on the floor, I have folded down the grey faux leather boot top all the way to the midpoint of the heel, exposed the reversible side of the boot top that has a beautiful grey and black diamond pattern, and then turned up the cuff on the bottom to create a wider width than my calf.

Llynda More black tapered heel boots and Golden Girl boot tops shown in two different configurations with jeans.
Black ‘More Love’ faux leather boots
with ‘Golden Girl’ boot tops by Llynda More

The same can be said for wearing boots with skinny jeans if you want a long, lean look. Wear dark blue or black skinny jeans with black knee high boots that have a heel and are form fitting to your calf for an ultimate long look. In the photo above, I am wearing a black vegan leather boot with a boot top that is form fitting to my calf and has a gold reversible side, so I created a nice cuff at the top. Although the gold cuff does create a break in the flow of the dark colors between the bottom of the heel and the top of the leg, it is nevertheless a small break, and the beauty of the gold color makes up for it. If looking your most slender at all times is your only goal, you will have to limit yourself to wearing black from head to toe every day with little to no decoration or color in your outfits that will break up the flow of dark material…. and you may find yourself getting rather bored. In that case, a little break here and there in your slenderizing flow is the next best thing such as the gold cuff at the top of the knee high boot as shown above.

For the mid-calf boot shown on the other leg, again, I manipulated the boot top into a style that creates an optical illusion to trick the eye of the beholder into thinking my calf is less wide than it actually is. I styled the boot top to have a ruffle at the bottom that is wider than my calf. Although the gold ruffle interrupts the flow of dark colored boots and skinny jeans, I was willing to sacrifice a tiny percentage of slenderizing effect in order to enjoy this fun, unique and eye-catching look.

These are just a few of many wonderful ways to wear boots with jeans. Every woman has a different body type and only she knows what styles she feels most comfortable wearing. With transformable boots that you can customize to accentuate your best characteristics, you can experiment to suit your individual body type and feel more confident than ever wearing boots with your jeans, leggings, and skirts.


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