How to Wear Ankle Boots with a Dress

This past Saturday happened to be a beautiful day in my hometown of Adelaide, so I threw on a dress and some ankle boots and off I went to enjoy a lovely late lunch with the husband.

And of course, in true Instagram Husband style, I made him take an outfit photo of me!

It was a hit with many of you, but one voice stood out from the crowd.

Over on the Sonia Styling Facebook page, Belinda said: OK I need tips Sonia, I just can’t do ankle boots and a dress, I try but ugh can’t do it!”

I made Belinda a promise to round up my best styling tips and pop them into a blog post, so here they are!

How to wear ankle boots with a dress

How to wear ankle boots with a dress

Surafina ‘Mi Corazon’ Shift Dress (size S/M) $89.95 | FRANKiE4 ‘VANESSA’ Ankle Boots (size 6) $299.95

Tip #1: Bare Legs, Neutral Boot

My first tip is for those glorious days where it’s warm enough to get your pins out.

In order to elongate your leg, opt for an ankle boot in a neutral hue such as beige, taupe or tan. It’s less of a stark and severe look than black, which can literally look like it’s cutting you off at the ankles and therefore makes your legs look shorter.

The height of the boot is less of a factor. As you can see in the above photo, I’ve gone for a slightly lower cut boot, but I also quite like a taller boot which sits at the very top of my ankle. Either way, just remember – bare legs, neutral boot.

Tip #2: The Boot, The Whole Boot & Nothing But The Boot

No matter the length of your dress, the key to an aesthetically pleasing look is to make sure you can see the entire boot.

Obviously this is easy to achieve with a short or knee length dress, but if a midi or maxi length is more your style, be mindful of whether you can see the ankle boot in its entirety.

As you can see below, this midi length sweater dress works well with a slightly lower cut ankle boot, as there’s just enough skin between the hemline of the dress and the top of the boot to completely show it off.

If you’re wearing a maxi dress, you can opt for a lower or higher cut ankle boot, but make sure there’s some leg showing in the form of a split or hemline that hits the top of the boot.

How to wear ankle boots with a dress

PassionQ Striped Cardigan from Whitehaven Emporium (size S/M) $60 | PassionQ Sleeveless Turtle Neck Dress from Whitehaven Emporium (size S/M) $55 | Spend-less Shoes ‘Wezzi’ Ankle Boots $59.99

Tip #3: Get Down To Details

It’s not just about the colour or height of the ankle boot – but the detail too.

To create a different look, try on styles that feature cut-out details on the front or side of the boot. This can help to elongate the leg and draw the eye all the way down.

Also, consider the fit of the top of the boot. For some people, a wider, looser fit at the top of the boot works for them. For others, a closer fit is the way to go. Try on both and see which you prefer.

Finally, play with prints and finishes. Don’t be scared to try an animal print ankle boot or one with a mock-croc or patent finish. You might just be pleasantly surprised at how fabulous they look on you!

Tip #4: Monochrome Magic

When it comes to wearing tights with ankle boots, monochrome is magic.

By pairing black opaque tights with black ankle boots, this creates a seamless look that also makes my legs look longer.

This would work for any colour, but just make sure you can match your tights as closely as possible to the colour of your ankle boots.

How to wear ankle boots with a dress

Bohemian Traders ‘Racer Lounge Dress’ (size XS) $139 | Forever New ‘Britney’ Opaque Tights $16.99 | Spend-less Shoes ‘Pia’ Ankle Boots $59.99

Tip #5: Try, Try and Try Again!

And the end of the day, fashion really is trial and error.

The only way you’re going to know what suits you is to try on different styles of ankle boots and see for yourself which ones look best on you.

Take photos in the changerooms, take along a fashionable (and honest) friend or family member, and above all – just give them a go!

Ankle boots add an effortless cool factor to any outfit and are a winter staple that should be embraced by everyone.

For more ankle boot styling tips and tricks, check out these posts:

What are your styling tips and tricks when it comes to wearing ankle boots with a dress?

This post features items provided to me for my editorial consideration in accordance with my Disclosure policy. This post contains affiliate links, which means if you click to buy the item, I earn a little commission but you don’t pay any extra.


  1. says

    Giiiiirl you’ve nailed it! I can usually get away with boot/dress combo because I’m eight feet tall, but I am still a bit iffy about ankle boots. I think I need to reconsider.

    Also how good is the Bohemian Traders racer dress? So warm, so comfy. Looks amazing on you x

  2. says

    Absolutely love the bare legs/neutral boot advice! And yes, try try try – different boot lengths, different dress lengths work in different ways with my (fairly average) height. X


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