With Tucked-In Jeans
Select a pair of skinny jeans. The jeans you wear need to hug your leg in order to fit beneath your riding boots without bunching up. For this reason, skinny jeans are the best option. If you do not have skinny jeans, you can fold another pair of jeans into your riding boots. Select the snuggest pair of jeans your own to accomplish this. Create a clean, even cuff by folding the bottom of each leg up. Roll up enough of the material to reveal your ankle. Pull the extra material at the back of each leg out and fold it over, creating a crease. Roll the leg of your jean up once more to create another cuff that can secure the cuff in place.
Consider the color and wash. A traditional blue denim works great with riding boots of all shades and styles, but you can also have a little fun by playing with skinny jeans in different colors. Other neutrals, like black and gray, can create a flattering and mature look. White skinny jeans have a clean yet daring appearance. Nowadays, jeans come in a variety of bright and pastel hues, as well. You can add a fun shock of color to an otherwise plain outfit simply by exchanging your standard blue jeans for a magenta jean or light orange jean.
Create a Western look with the right blouse. If you have brown riding boots, you can use them in a country-Western inspired outfit. While riding boots and cowboy boots are two very different beasts, brown riding boots are reminiscent enough of cowboy boots to make the look work. Wear a simple plaid button-down shirt. You can choose a shirt in a loose or fitted style, but either way, it should have some volume to it in order to balance out the sleek, slim silhouette of your lower half. Stick with medium to dark wash, blue denim skinny jeans. Accessorize as desired. You can wear simple jewelry or look for a few country-inspired pieces to accent this ensemble. Keep things fairly understated, though. Trading cowboy boots in for riding boots softens the Western style, so your accessories need to be softened, as well.
Go for an equestrian style. Riding boots are worn when riding horses, so adding a hint of equestrian flair to your style pays homage to this fashion fad's origins. Wear white or cream colored skinny jeans and black riding boots. Select a crisp, fitted shirt with clean lines. A standard white button-down shirt works well, but there is room for variety here as long as the silhouette remains clean. Slip a blazer on over your shirt. Wear a fitted blazer in black or navy blue for a more traditional look, or try a colored blazer for a fun spin on this style.
Attempt a casual look. The simplest way to wear your riding boots is with a standard blouse and your usual accessories. Select riding boots and skinny jeans in any color and style. Just make sure that the colors coordinate with the colors of your blouse. While most tops work well enough, the best option is a loose, flowing blouse made of soft, draping fabric. You can choose an empire-waist top to define your waist, or you could simply wrap a belt around an airy blouse at the waist to add the same sort of definition. Regardless, a shirt with volume creates a smart contrast with the skinny silhouette of your bottom half.
Covered by Flared Jeans and Trousers
Wear bootcut jeans. These jeans are aptly labeled as “bootcut” because they flair out just enough at the bottom to slip comfortably and loosely over boots of all heights and styles, including riding boots. This style works best when work with standard blue denim, but you can select any wash that appeals to you. If you do opt for a colored jean, stick with neutral colors like black, gray, white, and brown. Make sure your jeans are long enough to cover the majority of your boot but short enough to reveal the toe and heel of the boot.
Alternatively, trade your jeans for corduroys. As with bootcut jeans, you should wear your corduroys over the boots so that just the toes remain visible. Play with the color of your corduroys. You can wear corduroys in a traditional color, like tan, brown, black, or gray, or you can opt for a deep shade of a less traditional color, like olive green or midnight blue.
Dress the look up. This look can be turned into a business-casual style with relative ease when you select a pair of dark wash jeans or corduroys and black riding boots. Wear a simple button-down shirt over your pants or a well-fit blouse in a solid color or fine pattern. You can wear a blazer over the shirt to add a greater degree of professionalism to this look, or you could leave it off for a stronger casual hint. Accessorize, but keep it simple and classy. Plain metal jewelry is preferable over elaborate costume jewelry with large gemstones or bright colors.
Dress the look down. By wearing light to medium wash jeans and a less professional top, you can easily make black or brown riding boots work for a chic, easy-going weekend ensemble. Your top can be loose and flowing or snug and fitted. Since your jeans flare out at the bottom, the silhouette on your legs is not quite as skinny as it is when you wear skinny jeans with your riding boots. As a result, you can wear a loose, flowing shirt to maintain an overall air of balance or you can go with a snugger top to create a smoother, more streamlined appearance from top to bottom.
With a Skirt or Dress
Mix things up with a maxi skirt. Select a maxi with more volume so that the skirt does not cling to your boots. Also consider trying out a maxi skirt or dress with a long slit up the side to transform the look from dowdy and maternal to daring and flirty. To prevent the look from becomes too boxy or shapeless, wear something fitted at the top. Choose a fitted top with a daring neckline or exposed back when wearing a maxi skirt. If wearing a maxi dress, shrug a fitted cardigan, blazer, or jacket on over the dress to create more shape around your torso.
Show off your legs with a shorter skirt. Select a full, A-line, or pleated skirt to balance out the slim silhouette of your lower leg. Go with a mini skirt if you have riding boots that extend up to your knee or past it. The idea is to allow a portion of your leg to peek through in between the boot and lower hemline of the skirt. A knee-length skirt works well if your riding boots hit below the knee. Moreover, knee-length skirts flatter most body types and can be used to create both sweet and sexy looks. You have considerable room to play around with tops when wearing a shorter skirt. Fitted tops are often used to balance out the curves created by a flared out skirt, but whether you choose a shirt with a demure or sultry style is up to you.
Decide between bare legs and covered legs. If wearing a thin, flowing fabric, bare legs often looks best. For heavier materials, leggings and tights may look more appropriate. A knee-length skirt made of a stiff material like wool, tweed, corduroy, or denim is often associated with cooler weather, so tights often seem fitting in this instance. Short and long skirts made from light, breezy materials like linen and various cotton blends often look better when worn with bare legs, since this style is more commonly associated with warmer weather.
With Leggings
Pick out an appropriate color and texture. 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. 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.
Wear leggings with a skirt and riding boots. 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. 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.
Slip on a pair of shorts for a funky, fashion-forward style. 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. The shorts can be standard blue denim, but you can also have fun with a gray denim, colored khaki, or patterned pair of shorts. 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.
Try on a long tunic. 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.
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