Pointed toe ankle boots

From my own recollection not too many years ago, pointy toe shoes are not that popular. I remember my boyfriend even describing it as ugly at the time. But today they are not only mainstream fashion, they also look amazingly beautiful when styled with the right pieces. To explain this trend, some can simply explain that fashion trend is a circle. I also agree, but I’ll also give a lot of credit for the way the outfits keep evolving. It’s like basketball. Play styles are a circle, but the entire game of basketball has evolved with more experimentation or basically more trying to try different things. Pointed toe ankle boots are one of the most popular types of shoes. For this blog post, I have collected some of the best pointy ankle boot outfit ideas for you.

Pointed toe black leather ankle boots, wool coat and mini skirt


Pointed ankle boots are particularly suitable for winter. For an elegant look, you can wear a gray sweatshirt and a gray wool coat for the top. Combine them with a black leather mini skirt, stockings and the black pointy ankle boots.

Wear it with a black leather jacket and cropped mom jeans

black leather jacket pointed ankle boots

Wearing mom jeans won’t make you look like a mom as long as you style them right. (Sorry if I offended a mom. Moms can look cool too, no question.) To create this cool mom jean outfit, pair it with a white button-down shirt with vertical gray stripes. Wear black leather pointy toe ankle boots and drape a leather jacket over your shoulders for a touch of cool.

Wear it with a polka dot blazer and black cropped jeans

Pointed toe ankle boots and polka dot blazer

For those of you who need to dress casual for work, the blazer you wear can be a little more creative to spice up your work outfit. For example, wear a blue button down shirt and a black and white polka dot blazer over it. Black skinny jeans and pointed leather thong boots are the perfect complement to this professional looking stylish outfit. By the way, fans of the polka dot fashion trend might be interested in our blog post on polka dot dress outfit ideas.

Pointed-toe ankle boots, a black wool coat, and ripped skinny jeans

Pointed toe booties, black wool coat, ripped skinny jeans

There are always times when I just dress in black and look cool. This outfit isn’t the coolest of all black outfits imaginable, like a black leather jacket, but it has some warmth and coziness about it. Pair a black sweater with a black wool coat for top to pull off this look. Add a touch of roughness by wearing black skinny jeans and pointed toe ankle boots.

Suede ankle boots with long black wool coat and leggings

Suede Pointed Toe Ankle Boots Wool Coat

Seems like I mentioned some leather ankle boots, it’s time to talk about my other favorite: the suede ankle boots. Wear a black sweater dress with a long black wool coat for a neat outfit. Pair these pieces with black leggings and tan suede boots.

Ankle boots with a black blazer and gray skinny jeans

Pointed toe black blazer ankle boots

As a stylish and minimalistic outfit, you can wear a white V-neck t-shirt and a black blazer for the top. Add gray skinny jeans and black ankle boots to the equation. As simple as it looks, this is a very smart looking business casual work outfit. The key is that the parts fit.

Wear it with a Color Block Knit Sweater and a Leather Flare Mini Skirt

pointed toe boots leather flare mini skirt

If you want to add a touch of creativity and happiness to your all-black outfit, you can do something like this outfit idea. Instead of wearing a solid black sweater, wear a color block sweater that uses some shocking colors like pink. A flare mini skirt has an added cuteness compared to a pencil skirt. Complete your outfit with leggings and pointed toe boots.

Wear it with a gray oversized wool blazer

gray oversized wool blazer ankle boots

Here is another outfit idea related to mom jeans. Just wear a black sweater and oversized gray wool blazer for the top. Wear cropped mom jeans and pointy ankle boots to cover your buttocks.

Wear it with a comfortable knit sweater with a leather pencil skirt

black pointed toe booties comfortable knit sweater

Pointed toe ankle boots look really good with a minimal outfit. For example, wear them with a light gray oversized knit sweater and a black leather skirt. The look is clean and beautiful.

Green bomber jacket with pointed ankle boots

green bomber jacket pointed toe ankle boots

Pointed ankle boots and skinny jeans will make you look slim when paired with the right pieces. For example, wear a white blouse with your skinny jeans to optically move your waist up. Wear a green bomber jacket to offset the slight awkwardness of the tucked-in blouse. Complement this cool and durable outfit with black ankle boots.

Wear it with a black sweater dress and a long cardigan

black sweater dress pointy toe booties

For an all black outfit that looks feminine and elegant rather than dark, wear a black sweater dress and a long cardigan for the top. Wear black pointed toe leather ankle boots without leggings to complete the look.

Short leather jacket & black mini skirt

short leather jacket black mini skirt pointy boots

Sometimes you want to make yourself even taller by wearing a cropped jacket to visually push your waist up. As an example, you can wear a cropped black leather jacket over a white shirt with buttons for the top. Pair them with a black high waisted leather mini skirt and pointed suede boots. By the way, you might be interested in finding more short jacket outfit ideas here.

Gray suede ankle boots with a striped t-shirt and jeans

gray suede ankle boots black and white striped t-shirt

I’m mentioned in another blog post that I’m a fan of the black and white striped t-shirt. And one of my favorite ways to style it is to wear it with ripped jeans and white sneakers. This time we make the outfit more feminine by replacing the sneakers with gray suede ankle boots.

Pointed toe red ankle boots, black blazer and mini skirt

red pointed toe booties black blazer

When you’re wearing an all-black outfit, sometimes adding some red can spice up the whole look. For example, wear red pointed toe ankle boots, a black blazer and a black mini skirt for a low-profile yet beautiful look.

I hope you enjoy the list of pointy ankle boot ideas I have compiled. Really try some of these and see how they suit you. These outfits are generally pretty easy to pull off.

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