Stylish Ways to Wear Boots
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Stylish Ways to Wear Boots

Stylish Ways to Wear Boots

One of the most common questions that I am asked when working with style clients is which boots to wear with different pants, skirts, and dresses. It can be confusing, as small details, heel heights, and shaft heights can make a big difference in a boot working with a garment. I hope this blog helps you in putting together looks with everyone’s favorite shoe type.

Several elements determine if a boot works or not:

  1. Shaft height – Length of the part of the boot that comes up the leg
  2. Heel height
  3. Color
  4. Material
  5. Toe shape
  6. Heel shape/material – Wedge, chunky, spike, stacked
  7. Embellishments

As I discuss the options, I will be referring to these details.

How To Wear Boots With Full-Length Pants

When wearing full-length pants, the shape of the pant leg determines the best boot for the look.

How To Wear Boots With Full-Length Pants

Wide-leg pants need a toe that peeps out of the hemline or the foot can look stubby and the boot is lost. To elongate the leg, choose a color the same as the pants. Pointy-toed boots and elongated toes with a slight chop work best with these pants. Since the legs are wide, a tall boot can work underneath the pants. A heel (short or high) will continue the long look of the pants.

For straight-leg pants, you have lots of options, but a bootie is best since there is not much room in the leg of the pants. Flat or heeled options work well with straight legs. If you like a Chelsea style or the really flat ankle boots, this is the style to wear them with. Keep in mind that the really flat and short booties may make it look as if you are standing in a hole. They often have rounded toes as well which doesn’t not help the overall look.

Booties also work well with bootcut styles. A tall boot can work if the boot cut allows room, but we are looking for a shaft that doesn’t come up to the knee. A pointy or elongated toe looks great with the flare of the boot. Avoid overly rounded or stubby styles with bootcut pants.

For tapered-leg pants, we are looking for boots that allow for the pant leg to be tucked in or one that the hemline grazes over the top of the bootie. If you choose a short scrunchy bootie though, they may make the leg look heavy at the bottom, so I recommend avoiding that option. When tucking pants or jeans, try folding the pant around the leg so that the boot slides on more easily and the look is sleek.

How To Wear Boots With Cropped Pants

For cropped styles, we must think about leg exposure. We do not want to chop off the leg, and need to consider what, if anything, will cover the exposed part of the leg.

How To Wear Boots With Cropped Pants

Culottes and gauchos call for a tall boot, to the knee if possible. Keep in mind that if you are tall or petite, you will need to check the shaft length of the boot to decide if it is right for you. All tall boots are not the same height. For this look, we want a boot that comes up underneath the hem of the garment. You want a snug shaft to give a nice lean look– no scrunched shafts for these pants.

For a cropped flare or boot-cut pant, boots may not be the best option, but they can work. Booties are the one to choose. You will want the shaft of the boot to come high enough to land under the hemline. Skin showing between the boot and hemline will look odd and cut the leg in an unflattering place.

For wide-leg cropped pants, a tall bootie is a great choice, making sure that it extends up underneath the hemline. Choose a heeled version to elongate the leg. You will also want to choose a snug shaft that keeps the look long and clean.

How To Wear Boots With Dresses

Dresses are a place where boots can really complete a look, but a coordinating boot style is important to keep the look harmonious. Don’t just wear a boot to cover the legs. Make sure that the boot is a style match to the dress.

How To Wear Boots With Dresses

For shorter straight dresses, both tall boots and booties can work. Choose a snug shaft in any heel height. To complete the look, add hosiery or tights that match either the hemline of the garment or the color of the boot. For the sleekest look, choose a monochromatic combination of dress, tights, and boots in the same or similar shades. An over-the-knee boot works with this option for a very modern look.

For a knee-length dress, choose a tall, knee-high, snug-fitted boot or slightly slouched boot, or a mid-height boot with a heel. If this is a business or “dressy dress”, the boot should be dressy as well, leather or suede, and in good condition. A pointy toe is usually the best option here, but I won’t rule out a squared or slightly rounded toe since the dress gives us a long lean look.

For midi-length dresses, we want a boot that comes up underneath the hemline. Flat or heeled options work, but choose a snug shaft. A riding boot is a great option here.

For maxi-length dresses, a sleek bootie with a heel, a tall heeled, or a flat version will work. As stated above, though, make sure the boot is in alignment with the style of the dress. A peep-toe bootie can look great with this length.

How To Wear Boots With Skirts

Skirts and boots are a winning combination.

How To Wear Boots With Skirts

For a straight mini-skirt, a tall boot, to-the-knee, or over-the-knee works. If you want to wear a bootie, choose a snug medium height. This boot needs at least a slight heel to look best.

For a pencil skirt, a sleek tall boot, or a medium to tall bootie will keep the look sharp. Only choose the bootie if you are tall or long-legged, as it can chop the leg off visually. With the bootie, wear tone-on-tone hosiery so as not to break the line, choose a lower-cut bootie. We do not want a small wedge of skin showing midway down the calf, as this will cut the leg at an odd point, and make things look disjointed. Make sure this boot isn’t too slouchy, and in good repair. This is not the look for Western or rustic styles.

For the midi length full or aline skirt, a tall boot is the best option. The boot should meet or come up underneath the hemline. The heel can be flat, mid, or high. Avoid a slouchy boot with the volume of this skirt. A more casual western or BOHO-style boot can work with this shape if the skirt is in the same style.

I hope this guide helps you to wear your boots well!

Happy Styling,


Gail Scott

Gail Scott is Creative Director for Style and Beauty. She is a makeup expert and personal stylist. If you would like professional advice with Gail, please sign up for her exclusive 2-hour 1:1 session. Or schedule a 15 minute Style Chat with Gail to ask your questions.

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