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Beige ankle boots with all neutral colour outfit

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We all love wearing boots or want to wear boots more often but need inspiration on the different ways to wear boots throughout the year. There are different types of boots that need different types of styles which bring that pop to an outfit and show your style.

If you have short legs, favour slim-fitted boots with heels and pair them with slim-fitting mini skirts or slim pants, or tights in a matching colour to add length to your legs, for example, try wearing a mini skirt with ankle boots to create a longer leg line.

If you have wide feet, go for boots that have a round or almond-shaped toe rather than a pointed one. Avoid straps or buckles near the base of the boots and try wearing bootcut pants over them to minimize the width of your feet.

There are two ways to wear boots with pants and jeans: If you have slim/skinny fit pants, choose ankle or knee-high boots to tuck your pants/jeans into, slouch boots are comfier to use that style. If you have wider leg pants, like flared or boot cut jeans, choose narrow, smooth plain boots without buckles or straps and wear the pants over them.

For combining boots with skirts and dresses, the general rule is the shorter the skirt the longer the boots would be, thigh-high boots look great with short or mini-skirts and ankle-high boots go well with maxi skirts and dresses. Try knee-high slouch boots with longer skirts and wear mid-calf boots with a skirt or dress at the knee.

If you wear heeled boots with a fuller dress or skirt, they can fall just above the top of the boot. If your dress is more form-fitting, it should come to a few inches above the boot or knee.

Ankle boots are probably the most popular type of boots to wear daily. And if there's one staple your closet needs, it's the versatile ankle boot. They are generally easy to pair with lots of outfits. Booties end right at the ankle while ankle boots can end one to four inches above the ankle (low shaft). If the boots go any higher than that, they would be mid-calf boots.

Shorter heels in ankle boots can give you a strong cowgirl type look while a higher and more delicate look will go well with skinny jeans and a casual blouse or even a t-shirt. Classic ankle boots have a stacked heel or a chunky wedge, round toe or pointy toe which is more flattering.

Brown ankle boots
Brown high heel suede ankle boots
Black block heel ankle boots
Black leather ankle boots with embellishments
Brown suede fringe ankle boots
Black block heel leather ankle boots
red suede block heel ankle boots

ANKLE BOOTS can be easier to style with just about anything – from leggings to skirts, to dresses to cuffed jeans, rolled under jeans, cropped jeans and more with jeans, pants and midi-length dresses.

The cropped hemline on these jeans creates a frame for showing off your favourite boots, as a general rule, the hem of your jean to either meet the top of your boot shaft or leave max two-finger width of skin between the bottom of your hem and the top of the boot. If you are wearing skinny jeans, you can tuck them into your boots, if not, you can either cuff them or leave them on your boots. Make sure the boot openings are not awkwardly bigger than your pants. Pair your wide-leg or flared jeans with a pointed toe, block heel boots to elongate your legs.

Ankle boots with skinny jeans or leggings are a classic combination. Stiletto ankle boots look great with skinny jeans and leggings. The wide ankle opening booties are also flattering with a pair of figure-hugging leggings and an oversized turtleneck or cozy sweaters.

Ankle boots paired with a short shirt dress or neutral colour sweater dress, pleated skirts and tights create a sophisticated fall look. Try wearing them with opaque black tights and a short-cut sweater dress and flat ankle boots for a laid-back look. A monochromatic look, with boots, tights and skirt all in one colour looks perfect, such as a black pencil skirt or dress, black tights and black ankle boots.

Pointed-toe leather (mid to high shaft) boots work best for work clothes, you can wear pair of high shaft black leather boots with long wide-leg culottes, skinny pixie pants, pencil skirts or shirt dresses. Remember, it looks more professional when the booties hit the hem of your pant and show no skin.

Cowboy boots with jean
Brown mid calf strapped boots
Dark brown cowboy boots

You usually want boots or clothing to end at the slimmest parts of your body, but MID-CALF BOOTS end right at the thickest part of your calf and if not worn correctly they can make you look short and stumpy. COWBOY BOOTS, RAIN BOOTS, RIDING BOOTS and UGG BOOTS are among the most popular styles of mid-calf boots.

Cowboy boots create a distinctive, rugged, and slightly edgy look and can be used as a fashion statement. When you wear cowboy boots, try not to incorporate more than one Western-themed item into your outfit at once, like spurs, cowboy hats, and ponchos. And do not pair boots that have a busy design with a busy outfit.

Wear your cowboy boots over light colour skinny jeans, and denim and complete your look with a jacket or blazer. You can tuck them underneath your straight, boot or wide-leg jeans, but they are meant to be shown off, not hidden under the hem. You can wear your cowboy boots with long oversized knits or cardigans over leggings as well. Denim cut-off shorts and rompers are the perfect blends for cowboy boots. Choose boots that have some colour that matches any prints on your romper to make it all come together.

Loose, printed (floral etc.), silky, flowy mini or knee-length dresses, and sundresses can create an interesting contrast with the structured, rugged look of a cowboy boot. 

Open toe red suede booties
Black suede high heel booties
Red suede high heel booties
Suede high heel lita booties

Most BOOTIES come in the skinny high heel or the low block heel and you can wear them year-round.  They come in the form of Lita, Lace-up or wedge booties.  You don’t want booties to cut you off any higher than a couple of inches above your ankle because they can make you appear shorter.

You can pair booties with skinny ankle jeans, leggings or with long floaty boho dresses or sleek trousers and a button-down for the office. 

Make sure your jeans should never puddle or scrunch at the ankle, if so roll them up or tuck them in your booties. If you are not wearing a skinny cut, such as boyfriend jeans, then cuff the hems of your jeans to a few inches above the top of your booties. Generally, stick to anything between no skin and two finger widths of skin between the bottom of your hem and the top of the bootie. On the other hand, trousers are harder to style with booties, they should be exactly at the ankle or grazing the top of the boot.

When you pair with skinny jeans or leggings, make sure you add a longer jacket, tunic or sweater which keeps the silhouette in proportion.

When you pair them with dresses, look for booties that have a low-cut front on the ankle, opt for nude colour booties that elongate your legs. Try to choose a dress that is cut at the knee or above.

A monochromatic look pair well with booties, such as a combination of black ripped skinny jeans, a loose black top and black booties.

Black leather combat boots
Black leather combat boots
Brown combat boots

COMBAT BOOTS are especially famous among girls because of their edgy and sporty vibes. They offer great versatility, and you can pair combat boots with many different outfits, such as shorts, thighs, leggings, ripped jeans, pleated skirts, jeans, plaid shirts, graphic tees, chunky/oversized sweaters, knit jumpers, skater dresses, leather jackets. Option to pair them up with complementing-coloured pieces and matching accessories.

Black thigh high lace up boots
White high heel lace up boots
Brown high heel lace up boots

There is a variety of LACE UP BOOTS, the elegant ones are with a stiletto heel, pointed toe and long laces up to the top at the front. Pair your lace-up boots with stylish, skinny jeans, leggings or a relaxed or loose-fitting pair of jeans that you can cuff at the bottom to emphasize your shoe. But bigger cuffs can make your lower half appear shorter, so if you’re below average height then stick to smaller turn-ups. You can pair them with a midi or maxi skirt, maxi white or floral dresses for a more polished, dressed-up outfit. 

Brown knee high block heel boots
Brown suede knee high boots
Brown knee high boots

KNEE HIGH BOOTS tend to keep you warmer, and they’re much better at keeping rain, sleet, and snow from getting inside your boots. They can have buckles or straps, are typically zippered, and come in a variety of colours. They usually have a super straight and stiff shaft with minimal design and no slouching of the fabric.

Knee boots with a thicker stacked heel are more common instead of skinny heels. The thick heel balances the high shaft of the boot and looks balanced, perfect for everyday wear with jeans, leggings, trousers, and skirts. The sleeker the boots and the straighter the lines the better. The most common ones are brown and black suede or leather boots.

Black leather thigh high high heel boots
Black leather thigh high wedge heel boots
Black over the knee boots

The higher the shaft of the boots the more feminine the boots get. OVER THE KNEE and THIGH HIGH BOOTS are like ankle boots and booties, the only difference is a couple of inches. Over-the-knee boots have anywhere between a 20 and 25-inch shaft while a thigh-high boot has over 25 inches. You can also tell the difference between how the top of the boot ends. In thigh-high boots, the shaft gets larger towards to top so they truly go up to your thighs.

Non-shiny black leather or suede thigh-high boots are more common. They are sleek and chic, cover your entire leg and help you look tall and lean. 

Knee-high to over-the-knee boots are great for the winter and can help legs look more slender. The challenge, however, lies in how to wear them in such a way that is both classy and chic. Shorter hemlines tend to be a perfect fit with these shoes. If you are wearing a longer skirt, make sure that there is no skin showing between the hem of the skirt and the top of the boots.

Disclaimer : Mystylebox is a participant in the Amazon Services LLC Associates Program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. As Amazon Associates, we earn from qualifying purchases.


Black Ankle Boots with jeans
Black Ankle Boots with shorts
Black Army Boots with black jeans
Block Heel Red Ankle Boots with floral skirt
block heel White ankle boots with black pants
Black block heel lace up boots with cuffed jeans
White block heel ankle boots with denim outfit
Black thigh high block heel sock boots
Brown suede wedge ankle boots with neutral colour suit
Black combat boots with mini skirt
Black leather mid calf boots with jeans
Black leather ankle boots with ripped jeans
Black suede knee high boots with black jeans
Brown knee high rider boots with white mini flowy dress
Black combat boots with red shorts and jacket


Ankle boots


Low, blocked heel boots that cover the ankle. They are stylish, sturdy, and versatile. You can pair it with semi-formal or casual outfits such as boyfriend, straight or skinny jeans, flowy circle skirts, oversized knits, mini skirts, leather jackets and trench coats.

Wedge booties


Wedged heels, comfy boots, usually with suede surface and come in different styles. You can pair it with casual or dressy outfits depending on the style.

Army boots


Lace-up boots made of leather or nubuck with thickened upper parts to support the ankle and grooved flat sole have eyelets made of metal and a long tongue. You can pair it with denim, khaki or sporty pants, patterned shirts, hoodies, sweaters, and sports jackets.

Biker boots


Low-heeled boots with a loose-fit shaft that stops above the ankle but before the middle of the calf, usually have adjustable straps passing over the instep and around the ankle. You can pair it with casual outfits such as leather jackets and pants, jeans, tights, leggings, and t-shirts.

Chelsea boots


Close-fitting ankle-high boots with an elastic side panel and rounded toe cap, no laces, or zippers. Can be worn with casual outfits such as skinny or cropped pants and jeans, shirts, and t-shirts.

Desert boots


Lightweight, ankle-high suede boots with flat soles, open lacing with 2-3 pairs of eyelets and rounded toe. Can be worn with semi-casual outfits such as shirts, jackets, skinny or straight pants and jeans, oversize knits and sweaters, trench coats and leather jackets.

Combat boots


Laced heavy, chunky boots with a grooved flat sole and a rounded toe cap. You can pair it with any type of jeans, mini skirts, and grunge-style outfits.

Cowboy boots


Country style pointed-toe boots with a short boot shaft that stops at the middle of the calf, has a low angled heel, no lacing, and may have decorative stitches. Can be worn with bold casual outfits such as long or mid-length printed, flowy dresses or skirts with denim jackets.

Lita boots


Statement boots with chunky high heels and thick/sturdy texture. They come in a variety of colours and can be worn with dressy outfits such as any length dresses and skirts.

Lace-up boots


They are the boot versions of flat shoe styles such as oxford, brogues, and derby shoes. The elegant ones are with a stiletto heel, pointed toe and long laces up to the top at the front. Lace-ups can be as long as thigh-high as well. Can be worn with chic and dressy outfits.

Chukka boots


Ankle-high leather boots with suede or leather uppers, rubber flat shoes and open lacing with 2-3 pairs of eyelets. Can be worn with casual jeans and pants, cozy sweaters and cardigans, loose for lightweight layers, casual skirts and dresses.

Platform, Chunky boots


Statement boots that have thick soles, heels and a variety of colours and designs. You can pair it with casual or eye-catcher outfits.

Frye boots


Characterized by a harness belt around the ankles and mid-calf shaft with handles on the sides, has 2-inch heels, ankle, or knee-high length. The harness includes straps and a metal ring. You can pair it with casual outfits such as jeans, shorts and long, circle skirts and dresses.

Snow boots


Waterproof boots with wool lining. The most famous ones are moon boots. They come in different styles and colours. They can be worn with casual and sports outfits.

Shearling boots


Loose-fit flat boots made from sheepskin and assembled with the fleece on the inside. Can be worn with casual outfits, jeans, loose-cut coats and sports jackets.

Hiking boots


Water repellent and proof all over snug fit boots with rubber soles to protect feet and ankle during outdoor activities. Can be worn with casual and sports outfits.

Riding boots


Low heeled (1 inch or low, which was used to prevent the foot from sliding out of a stirrup, rounded toe), knee-length with a rounded top edge, leather boots fit tightly around the calves, have a zipper running down the back of the boot shaft. You can pair with down coats, raincoats, sheepskin coats, polo thirsts, fitted jackets, skinny pants and leggings.

Rain boots


Waterproof boots made of rubber or plastic, have a chunky rubber sole. Can be worn with casual outfits.

Slouch boots


Have an unstructured shaft that falls into folds, usually made of suede or other foldable textures. You can pair them with casual or dressy outfits such as jeans, leggings, mini or midi circle skirts and dresses.

Cuff boots


Have a fold-over upper, and a variety of heels, lengths, and styles. You can pair them with casual or dressy outfits such as jeans, leggings, mini or midi circle skirts and dresses.

Knee High boots

Knee High

Boots that rise to the knee or just below, tighter around the leg shaft and ankle, made of leather or suede. They are very versatile and can be worn with any style, mostly jeans, leggings, any length skirts and dresses.

Over the Knee boots

Over the Knee

Boots reach over the knee, usually tighter around the leg shaft, made of soft leather or suede, variety of heels. They have anywhere between a 20 and 25-inch shaft. You can pair them with casual or dressy outfits such as jeans, leggings, mini or midi circle skirts and dresses.

Thigh High boots

Thigh High

High boots that reach up to the thigh, and stretch the legs, are usually made of suede. Their shaft is approx. over 25 inches and gets larger towards the top. Can be worn with mini skirts and dresses, skinny pants, leggings, mid-length coats and jackets.

Sock boots


Heeled boots with the top of the boot fitting to the leg like a sock, made of suede, leather or neoprene. You can pair it with any style from casual to dressy.

Types of Flats
Types of Heels
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Types of Belts
Types of Hats
Types of Handbags
Jewelry Guide
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