5 Cute Fall Outfits With Black Ankle Boots - Simple Styling Tutorial

In this lookbook, I’m going to show you how to style ankle boots for fall. We’re going to be taking a look at different types of clothes - cropped jeans, skinny jeans, capri pants, a dress, tights, and a skirt - and see how you can make them work with ankle boots.

I’ve put together five cute fall outfits with black ankle boots - let’s take a look!

How to wear ankle boots with cropped jeans

1. Ankle boots with cropped jeans

To start, I’ve gone for cropped jeans. I find cropped jeans very flattering, and I particularly like styling them with ankle boots. The trick with ankle boots is to make sure you go for something that is relatively skinny around your ankle.

These boots aren’t super tight against my skin, but they come up close, making them a lot easier to style because you can tuck things in and leave things out without having too much trouble with the width of the top of the boot.

When it comes to cropped jeans, particularly, that cropped ankle on the boots will just sit under the hem quite nicely. I went for a pair in a mid-wash with a frayed hem and put them together with a plain white t-shirt. Just an easy, classic outfit.

As this is a really simple outfit, I decided to elevate it with a smart leather handbag. When it’s cold, you can layer a blazer and a chunky knit scarf over the top.

How to wear ankle boots in cold weather

2. Ankle boots with capri pants

For something a bit more formal, I really like pairing my boots with a smart pair of pants. Here I’m wearing a pair of capri pants. They have a crease down the front, so they are fairly tailored. If you have a longer pair of pants, you could tuck the hem into the top of your ankle boots.

I’ve paired the pants with quite a smart shirt, but I’ve styled it in a relatively laid-back fashion, just by leaving an extra button open and rolling up the sleeves. This is a smarter look but wearing it with ankle boots gives it an on-trend vibe.

What to wear with skinny jeans & ankle boots

3. Ankle boots with skinny jeans

On to skinny jeans, I’ve decided to pair mine with a mohair blend cardigan in that kind of grandad-style look. Cardigans and skinny jeans look great together, and a pair of booties just finish off the look.

When it comes to skinny jeans, there are a couple of different ways that you can style your ankle boots with them. You can either leave them out and go over the top of the ankle boot, which is my personal favorite.

You can also tuck your jeans into your boots. If your boots are slightly wider at the ankle, then that is when this looks best. Another way to style them is to do a turnup on your jeans, which gives your outfit a whole different vibe.

How to wear tights with ankle boots

4. Ankle boots with a dress

Onto a dress, which I think works really nicely with ankle boots.

There are a few little rules that I tend to stick to when styling outfits like this. I generally prefer midi dresses; if I’m going to go for a mini, I prefer the shape of the mini to be quite oversized. The reason for that is that it levels out the bottom half of me to feeling more slimline.

I don’t think that I would ever style a dress like this with a pair of ankle boots without a pair of tights. I really need that black longline running all the way down to my toes; it’s very lengthening and elongating at the same time.

I paired the dress with a vintage leather jacket to toughen up the look and make it feel a bit more sharp and rock-chick.

How to wear fall ankle boots

5. Ankle boots with a skirt

This skirt is quite a straight, pencil shape with a slit up the front. I really like the look of denim midi skirts with ankle boots together. I paired it with a cashmere crewneck to keep things really simple and quite slimline on my top half.

Those two pieces together are really lovely, and then the ankle boots just give the look a tougher edge.

Cute fall outfits with ankle boots

Hopefully, this lookbook has shown you just how versatile one pair of ankle boots can be in your wardrobe. Once you’ve got a perfect pair of ankle boots, don’t be afraid to have a go styling them with different pieces that you have.

Whether you’re going for something formal or laid-back and casual, go ahead and create a gorgeous ankle boots outfit that you love!

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 1 comment
  • Marie Marie on Sep 28, 2021

    Tonight I had them on with a Jean and dress up silk shirt .. those ankle boots are so sexy never get out of fashion