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Stylish Boots: The Complete Guide on Choosing & Styling

Stylish Boots: The Complete Guide on Choosing & Styling

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.

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. For 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.

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.


Ankle boots
Ankle boots
Ankle boots
Ankle boots

ANKLE BOOTS are probably the most popular type of boots to wear daily. If there's one staple your closet needs, it's the versatile ankle boot. They are generally easy to pair with lots of outfits. They 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.

Difference between Botties and Ankle Boots is that 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.

Ankle boots
Ankle boots

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.

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 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.

In winter, try wearing your wedges in boot form. Ankle or knee-high boot with a wedge heel can give your outfit the extra edge. Wear them over tights and with a shift dress and layered knits for a cool off-duty look.

Chelsea Boots :

Pointed Toes :

Block Heels :

Dress Boots :

Wedge Boots :

Lug-Soles :


Open toe red suede booties
Black suede high heel 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 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.

Block Heel Booties :

Dress Booties :

Combat Boots 

Combat boots
Combat boots
Combat boots
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.

Combats :

Lace-ups :

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. 

Buckles :


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, SLOUCH BOOTS and UGG BOOTS are among the most popular styles of mid-calf boots.

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

Western boots create a distinctive, rugged, and slightly edgy look and can be used as a fashion statement. When you wear western inspired 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 color 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 color 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. 

Western Boots :

UGG Boots :

Biker Boots:

Slouch Boots :


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.

Designer Tall Boots :

Franco Sarto Knee High Boots :

Naturalizer Knee High Boots :

Riding 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.

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