A smooth legging in a shade that matches your riding boots will create a crisp, trendy appearance, but you can play with color and texture to put different spins on your style.  Cable-knit leggings have a warm, cozy ambiance, while other textures and patterns, like lace-overlay, can have a flirty or playful air.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/f\/f6\/Wear-Riding-Boots-Step-13Bullet1.jpg\/v4-460px-Wear-Riding-Boots-Step-13Bullet1.jpg","bigUrl":"\/images\/thumb\/f\/f6\/Wear-Riding-Boots-Step-13Bullet1.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-13Bullet1.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"}  You can also wear leggings that contrast against the riding boot in order to show your boot off more. For instance, white leggings against black riding boots can create a dynamic contrast capable of making your riding boots stand out more.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/3\/36\/Wear-Riding-Boots-Step-13Bullet2.jpg\/v4-460px-Wear-Riding-Boots-Step-13Bullet2.jpg","bigUrl":"\/images\/thumb\/3\/36\/Wear-Riding-Boots-Step-13Bullet2.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-13Bullet2.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"} The most common thing to wear leggings and riding boots with are winter skirts and dresses.  Consider wearing smooth, solid leggings with a sweater dress for a sleek fall and winter look. To create a cozier appearance, trade the smooth leggings for a cable-knit pair.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/b\/b1\/Wear-Riding-Boots-Step-14Bullet1.jpg\/v4-460px-Wear-Riding-Boots-Step-14Bullet1.jpg","bigUrl":"\/images\/thumb\/b\/b1\/Wear-Riding-Boots-Step-14Bullet1.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-14Bullet1.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"}  When selecting a separate skirt to wear with your riding boots and leggings, choose a heavier material like wool or corduroy over something light and airy like linen.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/d\/d4\/Wear-Riding-Boots-Step-14Bullet2.jpg\/v4-460px-Wear-Riding-Boots-Step-14Bullet2.jpg","bigUrl":"\/images\/thumb\/d\/d4\/Wear-Riding-Boots-Step-14Bullet2.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-14Bullet2.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"} This look is a little bolder and less common than many others, but it can create a dramatic effect when done well.  Select a pair of fitted shorts that come down to the mid-thigh. Super short shorts can work, as well, but long shorts that come down to the knee reduce the effect by shortening the leg too much.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/a\/af\/Wear-Riding-Boots-Step-15Bullet1.jpg\/v4-460px-Wear-Riding-Boots-Step-15Bullet1.jpg","bigUrl":"\/images\/thumb\/a\/af\/Wear-Riding-Boots-Step-15Bullet1.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-15Bullet1.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"}  The shorts can be standard blue denim, but you can also have fun with a gray denim, colored khaki, or patterned pair of shorts.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/d\/d5\/Wear-Riding-Boots-Step-15Bullet2.jpg\/v4-460px-Wear-Riding-Boots-Step-15Bullet2.jpg","bigUrl":"\/images\/thumb\/d\/d5\/Wear-Riding-Boots-Step-15Bullet2.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-15Bullet2.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"}  This is also a good opportunity to play around with colored and patterned leggings. For example, you could try metallic leggings to give your style added sheen. When wearing colored or patterned leggings, though, you should avoid shorts with bright colors or patterns. You should also keep your shirt fairly subdued to prevent anything from clashing.    {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/a\/a4\/Wear-Riding-Boots-Step-15Bullet3.jpg\/v4-460px-Wear-Riding-Boots-Step-15Bullet3.jpg","bigUrl":"\/images\/thumb\/a\/a4\/Wear-Riding-Boots-Step-15Bullet3.jpg\/aid2707784-v4-728px-Wear-Riding-Boots-Step-15Bullet3.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class=\"mw-parser-output\"><p>License: <a rel=\"nofollow\" class=\"external text\" href=\"https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/\">Creative Commons<\/a><br>\n<\/p><p><br \/>\n<\/p><\/div>"} A loose tunic that comes down to your mid-thigh can create a stylish yet casual weekend look when matched with riding boots and simple leggings.  The loose, flowing appearance of a tunic balances out the slim-fit style of leggings and riding boots. For this look, smooth leggings that closely match the color of your boots work better than leggings in elaborate patterns or contrasting colors.

Summary:
Pick out an appropriate color and texture. Wear leggings with a skirt and riding boots. Slip on a pair of shorts for a funky, fashion-forward style. Try on a long tunic.